Top 86 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

$48
per adult

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 adult

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 adult

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

$64
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 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

$35
per adult

Architecture River Tour
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

$39
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

$30
per adult

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

$25
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 adult

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 adult

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 adult

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

$69
per adult

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 or magical evening 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... Read More

Categories: Adventures, Air, Balloon & Helicopter Tours

20 minutes

Free cancellation

$148
per adult

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

$35
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 adult

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 adult

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

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!

$50

$25
per adult

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!

$50

$25
per adult

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

$45
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

$25
per adult

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

$30
per adult

EagleRider Motorcycle Rental
Harley-Davidson® is the quintessential American motorcycle. Take the opportunity to climb aboard this iconic vehicle and experience your vacation destination from an entirely new perspective. Read More

Categories: Adventures, Tours & Sightseeing

1 day

$172
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 adult

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

$15
per adult

Explorer Pass: Choose up to 4 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
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 adult

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

$35
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

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

$49
per adult

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

$149
per adult

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

$34
per adult

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 adult

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

$39
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 adult

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 adult

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!

$50

$25
per adult

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 Michigan Skyline Cruise
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

$24
per adult

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

$75
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: Day Cruises & Water Activities, Tours & Sightseeing

30 minutes

Free cancellation

$25
per adult

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

$19
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

$40
per adult

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 adult

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 adult

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: 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 adult

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

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 adult

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

$129
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 adult

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!

$50

$25
per adult

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 adult

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 adult

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 adult

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 adult

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 adult

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

$39
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 adult

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!

$50

$25
per adult

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

$95
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 adult

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 adult

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 adult

Smartphone-Guided City Scavenger Hunt
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 adult

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 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
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

$15
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 adult

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 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

$59
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

$100
per adult

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

$18
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

$149
per adult

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