Top 152 Things to do in Chicago, Illinois

People head to the Windy City for more than just pizza , as they should. In the summer you can claim part of the Lake Michigan shoreline, and when temperatures dip Millennium Park opens up an ice skating rink. From fine dining to world-class shopping , there are plenty of fun things to do in Chicago, Illinois. Of course, the Chicago art and culture scene is also quite the draw, bringing in all types of travelers from around the globe. You’re bound to leave Chicago with a full stomach and lots to talk about.

1893 World's Fair Walking Tour with Bar & Food Stops
Perhaps more than any other event in Chicago's history, the 1893 World's Fair sparks imaginations and captivates visitors to the Windy City. Delve into the archives for an interactive tour, stopping along the way for games, food, and drink that... Read More

Categories: Culinary Experiences, Restaurants & Nightlife, Tours & Sightseeing

3 hours

Free cancellation

$58
per Traveler

2 Hour Segway Tour
Get a new perspective of the Windy City on this guided streamlined adventure. Glide past iconic landmarks, along the scenic shores of Lake Michigan, and through the city's most beautiful parks. This is an ideal tour for anyone with a... Read More

Categories: Tours & Sightseeing

2 hours

Free cancellation

$65
per Traveler

3 Hour Segway & Lakefront Tour
Sweep through the city in serious style—atop your own steerable Segway. Offered by the guys who first came up with the Segway tour, this tour guarantees you’re in good hands. Comb through Chicago's greatest hotspots and revel in the historical... Read More

Categories: Tours & Sightseeing

3 hours

Free cancellation

$70
per Traveler

360 Chicago Observation Deck
Soak up the Windy City at cloud level. The 94th-floor perch atop the John Hancock Center offers floor-to-ceiling windows showcasing Chicago’s top vistas. Admire the sparkling skyline, gaze across Lake Michigan's glimmering waters, and learn about the city’s famous landmarks.... Read More

Categories: Attractions

1 hour

Free cancellation

$18
per Adult

360 Chicago Observation Deck with Prosecco
Unobstructed 360-degree views and sparkling white wine awaits you in the heart of Chicago. With floor-to-ceiling windows, the 360 Chicago observatory offers you panoramic vistas of downtown Chicago, Lake Michigan, and 4 neighboring states. Read More

Categories: Attractions

1 hour

Free cancellation

$61
per Couple

75-Minute Architecture Riverboat Tour from Navy Pier
Equal parts boat and buildings, this river cruise features a widescreen perspective of the skyline and up-close views of its most iconic structures. Board an open-roof vessel and float with the current as an architecture expert shares the fascinating history... Read More

Categories: Day Cruises & Water Activities, Tours & Sightseeing

1 hour

Free cancellation

$35
per Adult

90-Minute Express Segway Tour
Glide your way through the Windy City on this 2-wheeled adventure. Ride past signature landmarks, through beautiful parks, and along the magnificent shoreline of Lake Michigan. This guided express Segway tour is the perfect way to see a lot of... Read More

Categories: Land Adventures, Tours & Sightseeing

1 hour 30 minutes

Free cancellation

$50
per Traveler

A Slice of Chicago Pizza Tour
Food is a big deal in Chicago, from hot dogs to 3-star restaurants, but if there's one food Chicagoans rave about most, it's undoubtedly Chicago-style pizza. This gooey, cheesy, deep-dish pie with its thick, cornmeal crust was invented at Chicago’s... Read More

$45
per Adult

Adler Planetarium
Journey beyond the moon, through the stars, and to the edge of the galaxy—all without leaving Chicago. At the Adler Planetarium, explore the exhibits, artifacts, and interactive displays that have been transporting visitors into the cosmos since 1930. Read More

Categories: Attractions

5 hours

Free cancellation

$31
per Adult

Amazing Scavenger Hunt Adventure
Embark on an interactive tour of Chicago and discover the city while using hints and completing unique challenges. See landmarks and historical locations as you solve clues on your smartphone that lead you on a memorable tour of the Windy... Read More

Categories: Adventures, Land Adventures, Tours & Sightseeing

3 hours

Free cancellation

$38
per Group

Architectural Masterpieces of the Loop Walking Tour
Chicago is home to some of America's most noteworthy architectural achievements, including the country's very first skyscraper. Take a fascinating journey back into history and learn all about the progression of architecture over the course of the city's history in... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$25
per Adult

Architectural Walking Tour of Chicago's River Walk
Avoid having a "been-there, done-that" experience in Chicago during a tour that shows you a hidden side of the Windy City. Explore the city's world-renowned architecture and learn about details of some of its buildings that are too often overlooked... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$25
per Adult

Art & Architecture Segway Tour
Explore Chicago's magnificent architecture on 2 wheels during a guided Segway tour. Cruise along the shores of Lake Michigan for prime views of the iconic skyline while your guide opens your eyes to the city's rich history. Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours 30 minutes

Free cancellation

$75
per Adult

Art Deco Skyscrapers: Riverfront Trolley & Walking Tour
Crane your neck and gaze at the looming Art Deco edifices that dot the streets of downtown Chicago. This classic architectural style is emblematic of the Windy City, and your tour takes you to 3 of its most shining examples... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$25
per Traveler

Art Institute of Chicago
Spend the day lingering over one of the finest collections of art in the world at The Art Institute of Chicago. Born as part of The Chicago World's Fair in 1893, this beloved institution’s formidable selection now showcases more than... Read More

Categories: Attractions

1 day

Free cancellation

$23
per Adult

Barrel Bus Craft Brewery Tour with Beer Samples
Craft beer is as popular as it has ever been, and this guided, all-inclusive brewery tour is the best way to taste a variety of exquisite brews while learning how they're made. Hop aboard the Barrel Bus and settle in... Read More

Categories: Culinary Experiences, Restaurants & Nightlife, Tours & Sightseeing

2 hours

Free cancellation

$65
per Traveler

Barrel Bus Craft Distillery Tour
Indulge in Chicago's highest quality spirits during a tour that takes you to the city's most renowned distilleries. This all-inclusive experience includes transportation on the quirky Barrel Bus, expert commentary, and plenty of tastings of skillfully distilled liquor. Read More

Categories: Culinary Experiences, Restaurants & Nightlife, Tours & Sightseeing

2 hours

Free cancellation

$65
per Traveler

Barrel Bus Prohibition-Themed Gangster Tour
Chicago's past is rife with the sordid deeds of infamous gangsters. Take a tour of the Windy City's history of organized crime during the Prohibition era and see some of the old stomping grounds of mobsters like Al Capone, John... Read More

Categories: Culinary Experiences, Restaurants & Nightlife

2 hours

Free cancellation

$35
per Traveler

Best of Chicago & 360 Chicago Observation Deck
From the North Side to the South Side, scenic drives to sky-high sights, this half-day excursion covers serious "Chi-town" ground. Cruise the Eastside Outer Drive, stop and smell the roses at the city's vibrant parks, and come close to the... Read More

Categories: Attractions, Tours & Sightseeing

5 hours 30 minutes

Free cancellation

$58
per Adult

Best of Chicago & Deep-Dish Pizza
Get ready to satisfy your craving for a true taste of Chicago. This comprehensive coach tour around the city’s finest sights concludes with a Chicago-style pizza with your name on it. Circle The Loop, Millennium Park, and more—stopping along the... Read More

Categories: Culinary Experiences, Restaurants & Nightlife, Tours & Sightseeing

5 hours 30 minutes

Free cancellation

$63
per Adult

Best of Chicago Tour
Let the Windy City carry you away as you explore Chicago top to bottom, scoping out the city's must-see parks, can't-miss lake views, and iconic architecture on this half-day tour. From the Loop to Lincoln Park, keep your camera at... Read More

Categories: Culinary Experiences, Restaurants & Nightlife, Tours & Sightseeing

4 hours

Free cancellation

$44
per Adult

Bike & Brew Tour
Enjoy a scenic bike ride along Chicago's famous Lakefront Trail as you journey to unique breweries for beer and food samples. Visit Chinatown and Pilsen neighborhoods where the brew culture is particularly strong. Your guide tells you all about the... Read More

$36
per Adult

Bike & Yoga Tour on Chicago's Lakefront Trail
Bike Chicago's tranquil, scenic Lakefront Trail in the quiet of the morning—a fantastic way to get to know the city and its people. Stop at one of the many sandy beaches along the way and meet up with a Vinyasa... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours 30 minutes

Free cancellation

$70
per Traveler

Bikes, Bites & Brews Bike Tour
Burn off calories almost as fast as you consume them. Your bike ride around Chicago pauses all pedaling before the city's tastiest culinary treats. From a bubbling slice of deep-dish pizza and a mustard-slathered hot dog to frosted cupcakes and... Read More

$79
per Adult

Blue Man Group
Blue Man Group, one of Chicago's longest-running shows, is a unique audiovisual experience—vibrant, colorful, and hilarious. Family-friendly and fabulously blue, this critically acclaimed show features innovative music and technology combined with good-humored social commentary. Read More

$55
per Traveler

Bucktown & Wicker Park Beer Tasting & Bar Tour
Get off the beaten track and into some of Chicago's most welcoming and history-filled bars during a beer-tasting tour that covers the Bucktown and Wicker Park districts. Visit drinking establishments that are teeming with character while learning fascinating tidbits about... Read More
Chicago CityPASS: 5 Must-See Museums & Attractions
Explore 5 of Chicago’s premier attractions at a discounted price, and enjoy special privileges with either VIP access or Fast Pass admission for most attractions. This pass is perfect if you want to explore the city on your schedule. Read More

Categories: Attractions, Tickets & Passes

9 days

Free cancellation

Save!

$208

$98
per Adult

Chicago Helicopter Experience
Experience the Windy City from above with a dazzling daytime helicopter tour—the ultimate way to take in the city's beauty. Learn about the history of the Chicago and see some of its most famous landmarks as you soar over the... Read More

Categories: Adventures, Air, Balloon & Helicopter Tours

20 minutes

Free cancellation

$128
per Traveler

Chicago Minibus Sightseeing Tour
Cruise around the Windy City in a stylish and comfortable minibus, as you scope out the city's cloud-skimming skyscrapers, art-filled parks, and charming neighborhoods. Along the way, let your knowledgeable guide share intriguing insight about Chicago's storied past and make... Read More

Categories: Tours & Sightseeing

2 hours

Free cancellation

$31
per Adult

Chicago Mob Tour: Criminals & Gangsters Bus Tour
Explore Chicago's underworld on this guided bus tour of gangsters and mobsters. Investigate Scareface Al Capone, The Untouchables, the Chicago Mob, John Dillinger, H. H. Holmes, and more. Read More

Categories: Attractions, Tours & Sightseeing

1 hour 30 minutes

$40
per Traveler

Chicago Shop & Shuttle
Enjoy roundtrip shuttle service between downtown Chicago and 2 of the Windy City's premier shopping destinations—The Shops at North Bridge and the Fashion Outlets of Chicago. Benefit from special discounts and rewards as you shop for deals at brand-name and... Read More

Categories: Attractions

5 hours

Free cancellation

$39
per Traveler

Chocolate Lover's Walking Tour
Satisfy your sweet tooth on this mouthwatering walking tour of the Magnificent Mile, stopping at several artisan chocolate boutiques for samples of their finest produce. Walk with an expert guide who leads you on a tasty tour of some of... Read More

Categories: Culinary Experiences, Land Adventures, Restaurants & Nightlife, Tours & Sightseeing

2 hours

Free cancellation

Save!

$25

$22
per Traveler

City Lights at Night Bike Tour
A smooth, 8-mile ride along Chicago's famed urban landscapes is particularly enchanting come nightfall. With knowledgeable commentary, awe-inspiring landmarks, and incredible scenic views, this relaxing evening bike tour inspires, informs, and illuminates. Read More

Categories: Land Adventures, Tours & Sightseeing

3 hours

Free cancellation

$48
per Adult

City Lights Tour by Absolutely Chicago Segway
Glide along the sidewalks and lakefront while taking in the luminous, iconic Chicago skyline and listening to your guide point out the city highlights. Your segway is equipped with lights to better see all the nuances of Chicago's stunning architecture... Read More

Categories: Tours & Sightseeing

2 hours

Free cancellation

$65
per Traveler

Classic Lake Michigan Tour
Sit back and relax as you gaze across the water and embrace the magnitude of Lake Michigan. In many ways, you feel as though you are heading out to sea, but the calmness of the water confirms that you... Read More

Categories: Day Cruises & Water Activities, Tours & Sightseeing

40 minutes

Free cancellation

$21
per Adult

Coffee Walking Tour
Given the city's famously chilly and windy weather, it's no wonder that Chicagoans love to cozy up with a hot cup of coffee. Delve into Chicago’s café scene with a tour of its best coffee shops, sipping java and nibbling... Read More

Categories: Culinary Experiences, Land Adventures, Restaurants & Nightlife, Tours & Sightseeing

2 hours

Free cancellation

Save!

$25

$22
per Traveler

Cruise with 3-Course Lunch Aboard Chicago Odyssey
A relaxing cruise aboard the Odyssey is the perfect way to take in views of Chicago's iconic skyline and waterfront landmarks. A perfectly prepared 3-course meal and lively DJ entertainment complements an already sophisticated experience and makes you feel like... Read More
Cupcake Walking Tour
There's simply no sweeter treat than the cupcake. Since the pint-sized-dessert trend swept Chicagoland, shops peddling these personal pastries have popped out of the oven by the baker's dozen. Sample your way through the best frostings and flavors in the... Read More

Categories: Culinary Experiences, Land Adventures, Restaurants & Nightlife, Tours & Sightseeing

2 hours

Free cancellation

Save!

$25

$22
per Traveler

Daily Bike Rental
Chicago is recognized as one of the most bike-friendly cities in the United States by cycling enthusiasts, and for good reason. Get set up with a comfortable bike and a detailed map of the city's numerous bike lanes and trails,... Read More

Categories: Land Adventures, Tours & Sightseeing

12 hours

Free cancellation

$41
per Adult

Dining at Hard Rock Cafe with Priority Seating
Dine like a rock star among pop, soul, and rock 'n' roll memorabilia—costumes and instruments from your favorite musicians—at the Hard Rock Cafe. Skip the lines with priority seating and enjoy a classic meal and a cookie. Read More

Categories: Culinary Experiences, Restaurants & Nightlife

2 hours

Free cancellation

Save!

$25

$23
per Traveler

Downtown & Skyline Vistas Trolley Tour
Climb aboard a charming trolley and dive into the dynamic parks, scenic drives, and vital waterways of the Windy City. Hear about the intriguing development of this Midwestern metropolis and enjoy various stops that offer unique perspectives and dramatic views... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$25
per Traveler

Evening Double-Decker Bus Sightseeing Tour
Cruise around the illuminated streets of Chicago aboard an open-top double-decker bus that allows you to see the city’s most spectacular sights. Listen to fascinating stories that reveal the windy city’s multilayered history while catching views of iconic towering skyscrapers.... Read More

Categories: Tours & Sightseeing

1 hour 15 minutes

Free cancellation

$29
per Adult

Evening Segway Excursion
Glide your way through the Windy City at night, humming past its iconic landmarks, zipping through its beautiful parks, and cruising near the shores of Lake Michigan. If you're lucky, you might even get to check out a stunning Chicago... Read More

Categories: Attractions, Tours & Sightseeing

1 hour 30 minutes

Free cancellation

$50
per Traveler

Evolution of the Skyscraper Walking Tour
Start with simple stones and end with high-strength steel as you embark on an architectural adventure to track the development of Chicago’s iconic skyscrapers. From stately columns to ostentatious façades, explore the Windy City’s building background from the ground up.... Read More

Categories: Land Adventures, Tours & Sightseeing

1 hour 30 minutes

$20
per Traveler

Explorer Pass: Choose 3 or 5 Museums, Attractions & Tours
Choose from more than 25 of Chicago's most amazing attractions, museums, and tours with this Explorer Pass and experience the city at your own pace. With your choice of up to 4 activities, enjoy access to famous locations as well... Read More

$72
per Adult

Exploring Old & New Architecture Walking Tour
Uncover the dynamic architectural scenes unfolding amid the bustling streets and intersections of downtown Chicago. See elegant stonework displayed next to modern high-rises and find out how the city’s architects approached the development of the Windy City’s urban landscape. Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$20
per Traveler

Extreme Speedboat Thrill Ride
Onboard Chicago's highest horse-powered passenger boat, feel the spray of the water and the whip of the wind as you slice through Lake Michigan. Your adrenaline kicks into gear when the captain accelerates into twists and turns—sometimes a full 360... Read More

Categories: Tours & Sightseeing

30 minutes

Free cancellation

$31
per Adult

Favorite Food & Drink Walking Tour
The smells of the city's most famous foods entice you right from the beginning on this delicious culinary tour. Enjoy famous Chicago-style pizza, hot dogs, craft beers, and a brownie from the folks who invented it. Read More

$55
per Adult

Fireworks over Navy Pier Segway Tour
Chicago's incredible lakefront is the setting for this outing to see some spectacular sights in the evening. A smooth Segway ride carries you past famous sites like Grant Park and Buckingham Fountain, giving you some great views of Lake Michigan... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours 30 minutes

Free cancellation

$75
per Adult

Fireworks Segway Tour
Hone your Segway skills as you take an evening journey past and through some of Chicago’s most popular attractions, and then enjoy a magnificent fireworks display over Navy Pier. Read More

Categories: Tours & Sightseeing

2 hours 30 minutes

Free cancellation

$65
per Traveler

Fireworks Speedboat Cruise
Blast off at dusk in an open-air vessel cruising at 45 miles per hour (72. 5 km/h) across Lake Michigan. Marvel at the magnificent skyline as you race across the lake, gripping tightly while your speedboat boat takes 180- and... Read More

$33
per Adult

Flanagan's Wake Dinner Theater
Flanagan is dead, but don’t be sad because remembering his life is all about laughs. Celebrate the life of dear Flanagan the Irish way—by hoisting a pint and joining in on the tales that unfold. Enjoy the set of the... Read More

$42
per Traveler

Fox River Valley Winetasting Tour
Pour a glass and taste the terroir of the Fox River Valley on this immersive look at the wineries and vintners scattered through northern Illinois. Savor rich reds, enjoy crisp whites, and explore innovative blends as you check out the... Read More

Categories: Culinary Experiences, Restaurants & Nightlife, Tours & Sightseeing

7 hours

Free cancellation

$158
per Adult

Gangster History Walking Tour
Explore the history of Chicago's underworld on this guided walking tour to some of the city's most infamous mob and gang-related spots. Learn about the outlaw days of the Second City, from Mad Sam Destefano to Al Capone, and see... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$18

$15
per Traveler

Gangster Tour
Learn about the sinister side of Chicago infiltrated by Al "Scarface" Capone, Sam Giancana, and Tony Accardo. Venture through the decades, visiting speakeasies, hangouts, and crime scenes of some of Chicago’s most notorious mobsters, while your guide provides interesting commentary.... Read More

Categories: Tours & Sightseeing

2 hours 30 minutes

Free cancellation

$76
per Traveler

Great Room Escape
Watch the door close and the lock turn as you get trapped in a room with only your wits to rely on. On this brain-tickling excursion, gather friends to help you tackle challenging riddles, puzzles, and clues that lead you... Read More

Categories: Adventures

1 hour

$40
per Traveler

Guided Tour of Legendary Chicago Sports Venues
Sports fanatics can get their fill of history of legendary Chicago sports venues while making stops for photo ops in front of The United Center, Wrigley Field, Soldier Field, and US Cellular Field. Your guided tour ends at Harry Caray's... Read More

Categories: Tours & Sightseeing

3 hours

Free cancellation

$40
per Adult

Historic Chicago Walking Bar Tour
Sip drinks and nibble on appetizers at 3 historic bars as you learn about the city's entertainment and party history while marveling at incredible architecture. Stroll at a leisurely pace with your guide to appreciate the iconic architecture and pubs... Read More

$39
per Traveler

Historic South Shore Tour
The South Shore of Chicago is bursting with cultural institutions, history, and beauty. Board a comfortable coach to take in the many sights along the southern lakefront such as Grant Park, Museum Campus, and the South Commons. Bring a camera... Read More

Categories: Tours & Sightseeing

2 hours

Free cancellation

$29
per Adult

Historic Treasures of Culture & Commerce Architecture Walking Tour
Uncover the Windy City’s exceptional architecture as you stroll between historic department stores, luxurious hotels, and towering office buildings. With a volunteer from the Chicago Architecture Foundation leading the way, explore the work of Chicago’s ambitious architects on this walking... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$20
per Traveler

Hop-On Hop-Off Bus Tour
Tour the sights of Chiacgo—renowned for its blues, jazz, comedy, shopping, and dining—at your own pace on a double-decker bus. This hop-on hop-off tour takes you all around the city’s major landmarks including Grant's Park, the Magnificent Mile, 360 Chicago,... Read More

Categories: Land Adventures, Tours & Sightseeing

1 day

Free cancellation

$35
per Adult

Hop-On Hop-Off City Tour
From parks and piers to markets and museums—Chicago’s a cultural mixing pot of the old, the new, the cutting-edge, and the classically historic. This flexible hop-on hop-off tour frees you up to discover every sight and neighborhood that strikes your... Read More

$35

$33
per Adult

Indoor Skydiving Experience at Naperville
Experience all the plummeting, free fall, and soaring sensations of skydiving without ever getting on a plane. This indoor skydiving experience puts you in a vertical wind tunnel, so you can float weightlessly in space for an unforgettable adrenaline rush... Read More

Categories: Adventures, Attractions

1 hour

Free cancellation

$70
per Traveler

Indoor Skydiving Experience at Rosemont
Experience all the plummeting, free fall, and soaring sensations of skydiving without ever getting on a plane. This indoor skydiving experience puts you in a vertical wind tunnel, so you can float weightlessly in space for an unforgettable adrenaline rush... Read More

Categories: Adventures, Attractions

1 hour

Free cancellation

$70
per Traveler

Italian Food Walking Tour
Taste your way through Chicago's vibrant Magnificent Mile and Gold Coast on this Italian food-focused walking tour. Try mouthwatering Italian beef, homemade meatballs and marinara as well as savory rice balls. Read More

Categories: Culinary Experiences, Land Adventures, Restaurants & Nightlife, Tours & Sightseeing

2 hours

Free cancellation

Save!

$25

$22
per Traveler

Kid-Friendly Bike Tour
Perfect for families with kids of all ages, this easy cruise through Chicago’s parks and along its lakefront trails is specially designed for tikes under 10. Cover 4. 5 miles (7 km) at an easy pace as you pedal to... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

Free cancellation

$42
per Adult

Lake View & Lincoln Park Beer Tasting & Bar Tour
Chicago's Lake View and Lincoln Park districts are home to a treasure trove of welcoming, locally owned bars and breweries. Join a group of like-minded beer lovers and visit the many drinking establishments that pepper these neighborhoods. Read More
Lakefront Neighborhoods Bike Tour
Pedal out of Downtown Chicago and tour the quaint and locals-favorite neighborhoods that surround the city's core. This leisurely 7-mile (11-km) loop covers ground in upscale Gold Coast, historic Old Town, and North Side beaches, with your guide narrating each... Read More

Categories: Land Adventures, Tours & Sightseeing

3 hours

Free cancellation

$48
per Adult

Lakefront Segway Tour
Experience Chicago's sights aboard a Segway on a guided excursion. Cruise through the Windy City, past iconic landmarks, gorgeous parks, and magnificent Lake Michigan. In just a few hours, see all of the top sights while listening to entertaining commentary.... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours 30 minutes

Free cancellation

$68
per Adult

Lakefront Speedboat Tour
Craving a way to make some waves? Cruise on a high-speed catamaran past Chicago's finest shore-side sights—adrenaline rush included. Board your turbo-charged vessel and shoot for Lake Michigan’s open waters. Along the way, your onboard guide provides city insights and... Read More

Categories: Adventures, Day Cruises & Water Activities, Tours & Sightseeing

30 minutes

Free cancellation

$22
per Adult

Land and River Architectural Tour
Appreciate Chicago’s architecture from the comfort of a coach and from the water as you cruise along the shoreline in a stunning streamliner yacht. Get a lay of the land by bus as you pass notable sights and landmarks, then... Read More

Categories: Tours & Sightseeing

3 hours 30 minutes

Free cancellation

$60
per Adult

Landmarks & Skyline Helicopter Tour
Take in Chicago's spectacular sights from a bird's-eye vantage point from the wide windows of a state-of-the-art helicopter. Soar over architectural landmarks and waterfront sights as a skilled pilot offers narration about the Windy City's past and present. Read More

Categories: Air, Balloon & Helicopter Tours, Tours & Sightseeing

30 minutes

Free cancellation

$179
per Traveler

LEGOLAND® Discovery Center Chicago
Let your imagination run wild as you build amazing creations, learn top tips from the Master Model Builders, pedal Merlin's Apprentice Bikes, and enjoy the unique 4-D cinema experience at the LEGOLAND® Discovery Center. Read More

Categories: Attractions

1 day

Free cancellation

Save!

$14

$13
per Adult

Lincoln Park Adventure
Park your car and grab a bike to experience Chicago at your own pace. As one of the most popular bike tours, this adventure around Lincoln Park takes you down lake-front trails free of any traffic. Enjoy a serene 2-wheel... Read More

Categories: Land Adventures, Tours & Sightseeing

3 hours

Free cancellation

$36
per Adult

Little Village & Pilsen Food Tour
Chicago's Pilsen and Little Village represent the heart of the city. Originally inhabited by Czechs and Eastern Europeans, these bustling West Side neighborhoods are now home to some of Chicago's best Mexican food, art, and culture. Take a guided food... Read More

Categories: Culinary Experiences, Restaurants & Nightlife, Tours & Sightseeing

3 hours 30 minutes

Free cancellation

$125
per Traveler

Loop & South Loop Beer Tasting & Bar Tour
Delve into Chicago's colorful past during a tour that takes you to some of the Loop and South Loop's most history-filled drinking establishments. This beer-tasting experience opens your eyes to the role that alcohol played in the enterprises of the... Read More
Loop Interior Architecture & Pedway Walking Tour
Strolling at a leisurely pace, follow your guide on a route weaving through buildings and secret shortcuts. Step inside landmark buildings like Marshall Field's Department Store and the Chicago Cultural Center to appreciate magnificent lobbies, corridors, and the underground Pedway... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$26
per Traveler

Macy's Star Shopper Package
Browse Macy's modern fashion while you walk through this historic department store. Formerly a Marshall Field's, the building is known for providing an extravagant and innovative shopping experience. Read More

Categories: Attractions, Land Adventures, Tours & Sightseeing

3 days

Free cancellation

$42
per Traveler

Medieval Times Dinner & Tournament
Hear ye, hear ye. Make haste to the castle to indulge in a night of feasting, combat, and revelry. The knights and horses of Medieval Times are here to thrill you with acts of showmanship and bravery reminiscent of legends... Read More

$66
per Adult

Millennium Park Walking Tour
Discover the fascinating history of Millennium Park on this quick tour around its unique grounds, where spectacular sculptures and art installations cover this iconic Chicago spot. Stand before the mirrored bean known as Cloud Gate, and snap photos of the... Read More

Categories: Land Adventures, Tours & Sightseeing

1 hour

$15
per Traveler

Millennium Park: Beyond the Bean Walking Tour
Stroll the grounds of Millennium Park to discover marvelous sculptures, sprawling gardens, and wide-open fields beneath geometric trellises. Originally designed to commemorate the new millennium, and highly criticized at the time, this park has become the crown jewel of Chicago’s... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$20
per Traveler

Minibus Sightseeing Tour with Chicago River Architecture Cruise
Explore the streets of the Windy City with an experienced local guide as you pop between gigantic lakefront parks and gleaming skyscrapers in a comfortable, climate controlled minibus. Snap photos of historic architecture, uncover public artwork by masters like Picasso,... Read More

Categories: Day Cruises & Water Activities, Tours & Sightseeing

3 hours 30 minutes

Free cancellation

$70
per Adult

Mobsters of the South Side Bike Tour
Pedal your way into Chicago’s seedy, crime-riddled past with a historical biking tour that takes you into what was once the city’s mob-run underbelly. Learn about Al Capone and the Chicago Outfit, learning about Chi-town’s dark side on this 13-mile... Read More

Categories: Land Adventures, Tours & Sightseeing

4 hours

Free cancellation

$60
per Adult

Modern Skyscrapers Walking Tour
Examine the rise of Chicago’s skyline as you wander between stunning modernist structures and elegant minimalist skyscrapers on this fascinating architectural tour. With a volunteer from the Chicago Architecture Foundation leading the way, uncover the newest buildings in the Windy... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$20
per Traveler

Museum Campus & Lakefront Segway Tour
Take in Chicago's finest sights from the back of a convenient and speedy Segway. This guided, 2-wheeled excursion covers 8 miles (13 km) of spectacular lakefront, with informative and entertaining stops at esteemed landmarks including Grant Park, Buckingham Fountain, and... Read More

Categories: Tours & Sightseeing

2 hours 30 minutes

Free cancellation

$74
per Traveler

Museums & Parks Sunset Bike Tour
Ride along the lakefront visiting parks and gardens as the refreshing lake breeze races across your face and the sound of waves smashing across the shoreline envelops you. Whether Chicago is your home town or this is your first time... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

Free cancellation

$42
per Adult

Mystic Blue Lake Michigan Boat Cruise
Take to the waters of Lake Michigan for a scenic evening getaway aboard the Mystic Blue. This cruise combines some great views of Chicago's waterfront with luxury and onboard entertainment that lets you enjoy your voyage in style. Read More
Navy Pier Segway Tour
Set your feet upon a futuristic Segway to glide on 2 wheels down Chicago's Navy Pier. Roll past the Ferris wheel, the anchor from the USS Chicago, and the sprawling stage venues, public parks, shopping plazas, and incredible views of... Read More

Categories: Land Adventures, Tours & Sightseeing

45 minutes

Free cancellation

$45
per Adult

Night City Bike Tour with Fireworks
Spend an enchanting evening biking to Chicago's main attractions as they're illuminated by the twinkling lights of the city. See The Bean sculpture at Millennium Park and the Crown Fountain's intriguing video art display. Top it all off with spectacular... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours 30 minutes

Free cancellation

$40
per Adult

Nighttime City Highlights Helicopter Flight
Experience the magic of Chicago's glittering skyline as you cruise over the city on this nighttime helicopter flight. Chauffeured through the sky by a knowledgeable pilot, learn about Chicago history while gazing at iconic buildings and sights from above. Read More

Categories: Air, Balloon & Helicopter Tours

20 minutes

Free cancellation

$153
per Traveler

Noble Square & Wicker Park Walking Tour with Food
The architecture, food, and people of 2 vibrant and fast-changing neighborhoods make for a great look at the state of Chicago today. See how Wicker Park has transformed from one of the city's roughest neighborhoods to one of its coolest,... Read More

$52
per Traveler

Odyssey Elegant Dinner Cruise
Set off for an elegant evening of dinner and dancing on stunning Lake Michigan. Your Odyssey dinner cruise offers the perfect reason to break out the cocktail attire, and combines course after mouthwatering course with a slow sail tracing Chicago’s... Read More

Categories: Culinary Experiences, Day Cruises & Water Activities, Restaurants & Nightlife, Tours & Sightseeing

2 hours 30 minutes

Free cancellation

Save!

$129

$114
per Traveler

Odyssey Elegant Dinner Cruise with Navy Pier Fireworks Show
Begin your luxurious evening cruise on Lake Michigan with the unique tastes of freshly prepared appetizers, and then make your way to the rooftop lounge to see the world-famous Chicago skyline. Read More

$149

$132
per Traveler

Open Your Eyes: Secrets of the Loop
Discover some of the hidden secrets of Chicago's bustling Loop, including hidden details and untold stories that add bits of color and texture to the city's overall narrative. Stroll through the streets with a guide and learn about the often-overlooked... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$25
per Adult

Panoramic North Side Tour
Experience the vitality and excitement of Chicago’s North Side, home to many flagship retail stores, one of the busiest financial centers in the world, and many cultural institutions. See iconic sights and landmarks such as the John Hancock Center, Wacker... Read More

Categories: Tours & Sightseeing

2 hours

Free cancellation

$29
per Adult

Passion Blues Tour with Dinner
Tap your toes to the lively tunes of Chicago's soulful blues. This authentic immersion into the city's deep musical history makes for a memorable evening of live guitar riffs, spellbinding rhythms, and traditional American eats. Read More

Categories: Tours & Sightseeing

3 hours

Free cancellation

$175
per Traveler

Pizza Walking Tour
Satiate your appetite with warm and savory deep-dish pizza as you pop into 4 of the best pizzerias in town. Follow your guide and see iconic places where movies were filmed in the Windy City as you gain knowledge about... Read More

Categories: Culinary Experiences, Land Adventures, Restaurants & Nightlife, Tours & Sightseeing

2 hours

Free cancellation

Save!

$25

$22
per Traveler

Private Brooklyn Bridge Park Photo Shoot
Let a professional photographer capture you in your best light during a stylish photo shoot that uses Brooklyn Bridge Park and the magnificent New York City skyline as your backdrop. End up with a set of beautifully lit and expertly... Read More

Categories: Tours & Sightseeing

1 hour

$269
per Group

Private Helicopter Tour for 2
Make it a night to remember with bird's-eye views of the Windy City's magnificent skyline during a thrilling helicopter tour. Perfect for a date or other special occasion, this adventure lets you see Chicago from a vantage point that few... Read More

Categories: Air, Balloon & Helicopter Tours, Tours & Sightseeing

30 minutes

Free cancellation

$499
per Group

Private Minivan: Chicago Midway International Airport (MDW)
Enjoy convenient private transportation between Chicago Midway International Airport (MDW) and your hotel in an economy minivan. For transfers to and from Chicago Midway International Airport, the areas to select from include: Read More

Categories: Airport Shuttles & Limos

40 minutes

Free cancellation

$69
per Vehicle

Private Minivan: O'Hare International Airport (ORD)
Enjoy convenient private transportation between O'Hare International Airport (ORD) and your hotel in the comfort of an economy minivan. For transfers to and from O'Hare International Airport, the areas to select from include: Read More

Categories: Airport Shuttles & Limos

40 minutes

Free cancellation

$69
per Vehicle

Private Session with a Local Photographer
Stand in front of Chicago’s most iconic landmarks as your photo is snapped by a professional photographer. Whether you’re posing before the mirror-plated Cloud Gate sculpture or the towering skyline, you’re sure to find amazing backdrops that result in high-resolution... Read More

Categories: Tours & Sightseeing

30 minutes

Free cancellation

$250
per Group

Private Standard Car: Chicago Midway Airport (MDW)
Enjoy convenient private transportation between Chicago Midway International Airport (MDW) and your hotel in the comfort of a standard car. For transfers to and from Chicago Midway International Airport (MDW), the zones to select from include: Read More

Categories: Airport Shuttles & Limos

30 minutes

Free cancellation

$67
per Vehicle

Private Standard Car: O'Hare International Airport (ORD)
Enjoy convenient private transportation between O'Hare International Airport (ORD) and your hotel in the comfort of a standard car. For transfers to and from O'Hare International Airport (ORD), the zones to select from include: Read More

Categories: Airport Shuttles & Limos

30 minutes

Free cancellation

$67
per Vehicle

Private SUV: Chicago Midway Airport (MDW)
Enjoy a relaxed journey in a high-quality SUV between the airport and your hotel. There’s no waiting in a taxi line, and guaranteed fixed rates include flight tracking, 1 hour of wait time, and all taxes, tolls, and tips. Prices... Read More

Categories: Airport Shuttles & Limos

45 minutes

Free cancellation

$115
per Vehicle

Private SUV: Chicago Midway Airport (MDW)
Enjoy convenient private transportation between Chicago Midway International Airport (MDW) and your hotel in the comfort of an SUV. For transfers to and from Chicago Midway International Airport (MDW), the zones to select from include: Read More

Categories: Airport Shuttles & Limos

30 minutes

Free cancellation

$80
per Vehicle

Private SUV: Chicago Midway Airport (MDW)
Enjoy convenient, top-of-the-line private transportation between Chicago Midway International Airport (MDW) and your hotel in the comfort of an SUV. For transfers to and from Midway Airport, the areas to select from include: Read More

Categories: Airport Shuttles & Limos

30 minutes

Free cancellation

$113
per Vehicle

Private SUV: Chicago Midway Airport (MDW)
Enjoy convenient private transportation between Chicago Midway International Airport (MDW) and your hotel in the comfort of an SUV. For transfers to and from Chicago Midway International Airport, the areas to select from include: Read More

Categories: Airport Shuttles & Limos

40 minutes

Free cancellation

$100
per Vehicle

Private SUV: Chicago O'Hare International Airport (ORD)
Enjoy a relaxed journey in a high-quality SUV between the airport and your hotel. There’s no waiting in a taxi line, and guaranteed fixed rates include flight tracking, 1 hour of wait time, and all taxes, tolls, and tips. Prices... Read More

Categories: Airport Shuttles & Limos

1 hour

Free cancellation

$120
per Vehicle

Private SUV: Midway International Airport (MDW)
Enjoy convenient private transportation between O'Hare International Airport and your hotel in the comfort of an SUV. Read More

Categories: Airport Shuttles & Limos

45 minutes

Free cancellation

$120
per Traveler

Private SUV: O'Hare Airport (ORD)
Enjoy convenient, top-of-the-line private transportation between O'Hare International Airport (ORD) and your hotel in the comfort of an SUV. For transfers to and from O'Hare International Airport, the areas to select from include: Read More

Categories: Airport Shuttles & Limos

25 minutes

Free cancellation

$63
per Vehicle

Private SUV: O'Hare International Airport (ORD)
Enjoy convenient private transportation between O'Hare International Airport and your hotel in the comfort of an SUV. Read More

Categories: Airport Shuttles & Limos

1 hour

Free cancellation

$120
per Traveler

Private SUV: O'Hare International Airport (ORD)
Enjoy convenient private transportation between O'Hare International Airport (ORD) and your hotel in the comfort of an SUV. For transfers to and from O'Hare International Airport (ORD), the zones to select from include: Read More

Categories: Airport Shuttles & Limos

30 minutes

Free cancellation

$80
per Vehicle

Private SUV: O'Hare International Airport (ORD)
Enjoy convenient private transportation between O'Hare International Airport (ORD) and your hotel in the comfort of an SUV. For transfers to and from O'Hare International Airport, the areas to select from include: Read More

Categories: Airport Shuttles & Limos

40 minutes

Free cancellation

$107
per Vehicle

Private Town Car: Chicago Midway Airport (MDW)
Enjoy convenient, top-of-the-line private transportation between Chicago Midway International Airport (MDW) and your hotel in the comfort of a town car. For transfers to and from Midway Airport, the areas to select from include: Read More

Categories: Airport Shuttles & Limos

30 minutes

Free cancellation

$82
per Vehicle

Private Town Car: Midway International Airport (MDW)
Enjoy convenient private transportation between Midway International Airport and your hotel in the comfort of a town car. Read More

Categories: Airport Shuttles & Limos

45 minutes

Free cancellation

$95
per Traveler

Private Towncar: Chicago Midway Airport (MDW)
Enjoy a relaxed journey in a high-quality towncar between the airport and your hotel. There’s no waiting in a taxi line, and guaranteed fixed rates include flight tracking, 1 hour of wait time, and all taxes, tolls, and tips. Prices... Read More

Categories: Airport Shuttles & Limos

45 minutes

Free cancellation

$77
per Vehicle

Private Towncar: Chicago Midway Airport (MDW)
Enjoy convenient private transportation between Chicago Midway International Airport (MDW) and your hotel in the comfort of a towncar. For transfers to and from Chicago Midway International Airport, the areas to select from include: Read More

Categories: Airport Shuttles & Limos

40 minutes

Free cancellation

$75
per Vehicle

Private Towncar: Chicago O'Hare International Airport (ORD)
Enjoy a relaxed journey in a high-quality towncar between the airport and your hotel. There’s no waiting in a taxi line, and guaranteed fixed rates include flight tracking, 1 hour of wait time, and all taxes, tolls, and tips. Prices... Read More

Categories: Airport Shuttles & Limos

1 hour

Free cancellation

$86
per Vehicle

Private Towncar: O'Hare Airport (ORD)
Enjoy convenient, top-of-the-line private transportation between O'Hare International Airport (ORD) and your hotel in the comfort of a towncar. For transfers to and from O'Hare International Airport, the areas to select from include: Read More

Categories: Airport Shuttles & Limos

25 minutes

Free cancellation

$61
per Vehicle

Private Towncar: O'Hare International Airport (ORD)
Enjoy convenient private transportation between O'Hare International Airport and your hotel in the comfort of a towncar. Read More

Categories: Airport Shuttles & Limos

1 hour

Free cancellation

$96
per Traveler

Private Towncar: O'Hare International Airport (ORD)
Enjoy convenient private transportation between O'Hare International Airport (ORD) and your hotel in the comfort of a towncar. For transfers to and from O'Hare International Airport, the areas to select from include: Read More

Categories: Airport Shuttles & Limos

40 minutes

Free cancellation

$80
per Vehicle

River & Lake Speedboat Architectural Tour
In a turbo-charged catamaran, glide up the Chicago River for a closer look at the city's vibrant and diverse architecture, before the power is cranked up for a wind-whipping ride along the lakefront. While you cruise, your expert guide offers... Read More

Categories: Day Cruises & Water Activities, Tours & Sightseeing

1 hour 15 minutes

$35
per Adult

Rivers, Parks, & Architecture Tour
Explore the rivers, parks, and architecture that truly make Chicago unique as you cruise along behind your guide on a Segway. Learn all about the iconic landmarks of the city as you pass by, snapping photos of all your favorite... Read More

Categories: Tours & Sightseeing

2 hours

Free cancellation

$71
per Traveler

Riverwalk Food Tour
Get to know the culinary offerings of the Chicago Riverwalk with a tour that introduces you to the great tastes of the Windy City. See the breathtaking architecture along the Chicago River and some of the best views this city... Read More

Categories: Culinary Experiences, Land Adventures, Restaurants & Nightlife, Tours & Sightseeing

2 hours

Free cancellation

Save!

$25

$22
per Traveler

Scenic Helicopter City Tour
Hop aboard a state-of-the-art helicopter and take in Chicago's magnificent sights from a bird's-eye perspective. This thrilling adventure lets you appreciate the Windy City's many landmarks from a sky-high vantage point that few get to experience. Read More

Categories: Air, Balloon & Helicopter Tours, Tours & Sightseeing

15 minutes

Free cancellation

$150
per Traveler

Scooter Rental with Scootaround
Rent a scooter during your time in Chicago for convenient and worry-free mobility, whether you’re traveling for business, are on vacation, or are just passing through. Read More

Categories: Tours & Sightseeing

1 day

$86
per Traveler

Secret Tavern Food & Drink Tour
Get off the beaten track and into Chicago's most out-of-the-way taverns, where the locals go to get away from the crowds and unwind. This guided tour is the best way to explore the bar scene lens of native Chicago mixologists,... Read More

Categories: Culinary Experiences, Restaurants & Nightlife, Tours & Sightseeing

3 hours 30 minutes

Free cancellation

$125
per Traveler

Segway at Sunset Tour
Zip around on a speedy Segway to view Chicago's gorgeous skyline at sunset, flying over paved trails along Lake Michigan's waterfront. Get a new perspective on the Windy City from your friendly guide as you have a blast whipping through... Read More

Categories: Tours & Sightseeing

2 hours 30 minutes

Free cancellation

$68
per Adult

Shared Shuttle:  Chicago Midway International Airport (MDW)
Enjoy convenient and cost-effective shared transportation between Midway International Airport and your hotel aboard a shuttle. For transfers to and from Midway International Airport, the areas to select from include: Read More

Categories: Airport Shuttles & Limos

1 hour

Free cancellation

$26
per Traveler

Shared Shuttle: O'Hare International Airport (ORD)
Enjoy convenient and cost-effective shared transportation between O'Hare International Airport and your hotel aboard a shuttle. For transfers to and from O'Hare International Airport, the areas to select from include: Read More

Categories: Airport Shuttles & Limos

1 hour

Free cancellation

$31
per Traveler

Shop, Dine & Shuttle from Downtown or O'Hare International Aiport
Enjoy roundtrip shuttle service between downtown Chicago or O'Hare International Airport and Chicago's premier shopping outlet destinations—the Fashion Outlets of Chicago. Benefit from special discounts and rewards as you shop for deals at brand-name and high-end retailers and grab a... Read More

Categories: Attractions, Land Adventures, Tours & Sightseeing

1 day

Free cancellation

$46
per Traveler

Shop, Explore, Play or Spa at The North Bridge Shops
The Shops at North Bridge span 6 blocks of Michigan Avenue, just steps from downtown Chicago's beautiful lakefront. Benefit from special discounts and rewards as you shop for deals at brand-name and high-end retailers in the heart of the Windy... Read More

$40
per Traveler

Skyscraper Segway Tour
Chicago's iconic skyline is marked by some of the tallest and most architecturally impressive skyscrapers in the country. Step aboard an easy-to-operate Segway and cruise along the city's streets during a tour that lets you marvel at these magnificent buildings... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours 30 minutes

Free cancellation

$75
per Adult

Small-Group Little Arabia Food Tour
Fresh bread slathered with olive oil-splashed vegetable spreads, grilled meats scattered wiith fragrant herbs and jewel-like pomegranate seeds, and desserts perfumed with rosewater and honey—the fresh and luxurious flavors of Middle Eastern cuisine are at your fingertips on this delicious... Read More

Categories: Culinary Experiences, Land Adventures, Restaurants & Nightlife, Tours & Sightseeing

3 hours 30 minutes

Free cancellation

$90
per Traveler

Small-Group Little India Food Tour
Savor the flavors of the subcontinent right in the heart of the Windy City on this delicious, food-focused walking tour in Chicago's Little India neighborhood. Sample dishes from India, Pakistan, and Bangladesh, browse specialty shops, and even get a traditional... Read More

Categories: Culinary Experiences, Land Adventures, Restaurants & Nightlife, Tours & Sightseeing

3 hours 30 minutes

Free cancellation

$90
per Traveler

SpaFinder Gift Card
Pamper yourself with a facial, sweat it out in hot yoga, or ease into a state of calm with a soothing massage—however you find your bliss, the Spafinder gift card can get you there. With more than 20,000 participating wellness... Read More

Categories: Spas & Beauty

$50
per Adult

Spirit Fireworks Dinner Cruise
Enjoy fireworks perfectly synchronized to music over Lake Michigan on this cruise designed for fun. Climb aboard and sip cocktails on the open-air rooftop deck. Enjoy a savory dinner as you cruise along the picturesque Chicago coast. Read More

$129

$114
per Traveler

Spirit of Chicago Dinner Cruise
Savor an evening of dinner, drinks, and dancing—all while cruising Chicago's stunning lakefront. Dressed in your favorite cocktail attire, your voyage aboard the luxurious Spirit of Chicago features a gourmet buffet feast and live DJ music set against the Windy... Read More
Sunday Brunch on the Chicago Odyssey
Climb aboard the Odyssey for a delicious brunch cruise around Lake Michigan. Cap off an incredible weekend, or have a group celebration, with a bounty of delicious food combining both savory and sweet that's served amidst amazing views of the... Read More
Sweets & Spirits Dessert Tour
Indulge your sweet tooth and your thirst as you sample the best desserts and cocktails in Chicago. Gorge on samples of chocolates and baked goods before washing it down with creative cocktails. The city is your playground as you partake... Read More

Categories: Culinary Experiences, Land Adventures, Restaurants & Nightlife, Tours & Sightseeing

2 hours 30 minutes

Free cancellation

$55
per Adult

The Chicago Theatre Marquee Tour
Share the same center stage spotlight that was cast on legends like Dean Martin and Frank Sinatra. This behind-the-scenes tour through The Chicago Theatre Marquee Tour ensures a starry-eyed evening of fascinating history and sheer elegance. Read More

Categories: Attractions

1 hour

Free cancellation

$13
per Adult

The Field Museum
What sprung from the 1893 World's Columbian Exposition now stands as Chicago's Field Museum. Its neo-Classical buildings are stocked with more than 25 million artifacts—some up to 4. 6 billion years old. This vast collection of fascinating relics exhilarates history... Read More

Categories: Attractions

5 hours

$38
per Adult

The Ultimate Architecture Tour
Art Deco icons, industrial-era giants, and ultra-modern, glass-and-steel skyscrapers—Chi-town's packed with impressive edifices, and each one has a story to tell. Hear the tall tales behind Chicago's architectural gems on this intriguing look at the Windy City's must-see structures. Read More

Categories: Land Adventures, Tours & Sightseeing

1 hour 30 minutes

Free cancellation

$22
per Traveler

Tommy Gun's Garage Dinner Show
If you know the password to get into this swanky speakeasy, travel back in time to the roaring 1920s complete with gangsters and flappers. Savor a 3-course dinner followed by a raucous musical comedy revue and get a chance to... Read More

$65
per Traveler

Walking Tour of River North & Cathedral District
Learn all about Chicago's rebirth as the "Second City" after the infamous Great Fire of 1871 during this fascinating guided tour. A friendly guide takes you on a trip through time and explains the amazing story of tragedy and resilience... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$25
per Adult

Walking Tour of the Dazzling Interiors of the Loop
Experience the energetic buzz of activity that thrives in the Loop, Chicago's commercial core. Join a guide and see some of this district's most dazzling buildings and interiors, where businesspeople and politicians rush from meeting to meeting and tourists scurry... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$25
per Adult

Walking Tour of The West Loop & Wolf Point
All of Chicago's neighborhoods are rich with culture, but the West Loop is perhaps the closest and most accessible off-the-beaten-path experience for getting to know this world-famous city while sticking close to downtown. Explore this district and marvel at epic... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

$25
per Adult

We Gotta Bingo Dinner Theater Experience
Spend a raucous evening at Der Brew-Ha-Ha, a 200-seat German beer hall, where you eat, dance, drink, and play bingo in a theater experience. Soak up the jolly atmosphere as you become embroiled in a good-natured conflict between 2 rival... Read More

$51
per Adult

Wheelchair Rental with Scootaround
Rent a wheelchair during your time in Chicago for convenient and worry-free mobility, whether you’re traveling for business, are on vacation, or are just passing through. Read More

Categories: Tours & Sightseeing

1 day

$90
per Traveler

Willis Tower Skydeck & The Ledge
In 60 seconds, your elevator climbs to the 103rd floor of the second-tallest building in the United States. From the breathtaking Skydeck, marvel at sights reaching 4 states, scan Chicago's iconic skyline, and venture out onto The Ledge—a thrilling glass... Read More

Categories: Attractions

3 hours

Free cancellation

Save!

$18

$16
per Adult

Wine Tour of Southwest Michigan
Sip and swirl your way around the southern edge of Lake Michigan, stopping off at award-winning wineries scattered along Michigan's fertile shores. Chat with vintners about the benefits of a Midwest climate on grape quality, sample various vintages from around... Read More

Categories: Culinary Experiences, Restaurants & Nightlife, Tours & Sightseeing

7 hours

Free cancellation

$158
per Adult

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