Top 55 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.

2 Hour Segway Tour by City Segways
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 person

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 person

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
Couple ( 2 Travelers )

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 person

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 person

Beautiful: The Carole King Musical
Enjoy award-winning music alongside the inspiring story of music legend Carole King. Beautiful takes you on a journey through history to share the story of chart-topping songwriting, work and personal relationships, and amazing reflections on a life filled with warmth.... Read More

Categories: Events & Shows, Sports, Tickets & Passes

2 hours 45 minutes

$95
per person

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

$63
per person

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

$60
per person

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

$48
per person

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 person

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

$96
per person

Chicago Shop & Shuttle by Shop America
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 person

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 person

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 person

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 person

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 person

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

$92
per person

Favorite Food 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 person

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 person

Go Chicago Card
Discover Chicago’s finest museums, restaurants, cruises, and more with your Go Chicago Card. Combining some of the city’s top attractions, with advantages such as convenient discounts and skip-the-line access, this pocket-sized perk ensures you see all the Windy City has... Read More
GO Private Express - 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 person

GO Private Express - 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 person

GO Private Express - 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 person

GO Private Express - 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

$95
per person

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 person

Historic Chicago Walking Bar Tour by Chicago Detours
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 person

Historic South Shore Tour by Gray Line Chicago
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 person

Hop-On Hop-Off City Tour by Chicago Trolley & Double Decker
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 person

Indoor Skydiving Experience at Naperville by iFLY
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

1 hour

Free cancellation

$70
per person

Indoor Skydiving Experience at Rosemont by iFLY
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

1 hour

Free cancellation

$70
per person

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 person

Legendary Marquee Theatre 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 ensures a starry-eyed evening of fascinating history and sheer elegance. Read More

Categories: Attractions

1 hour

Free cancellation

$15
per person

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 person

Loop Interior Architecture & Pedway Walking Tour by Chicago Detours
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 person

Macy's Star Shopper Package by Shop America
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 person

Made in Chicago Designer Shopping Tour
Discover Chicago’s most exquisite designers, including Alice & Olivia, Kimberly Ovitz, and Wren, as you stroll through a unique and creative marketplace. Your personal shopping stylist shares success stories and local trivia while leading you to boutiques that only a... Read More

$50
per person

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

$65
per person

Museum Campus & Lakefront Segway Tour by Absolutely Chicago Segway
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

$69
per person

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

$126
per person

Panoramic North Side Tour by Gray Line Chicago
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 person

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

$206
per person

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 person

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 person

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 person

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 person

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 person

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

$15
per person

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 person

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

$122
per person

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 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

$23
per person

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 person

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 person

Windy City Neighborhood Boutiques Tour
Explore boutiques in 2 of Chicago's hippest neighborhoods—Bucktown and Wickerpark. Your personal stylist leads you to the hard-to-find boutiques that you won’t find back home or along the Magnificent Mile. Read More

Categories: Tours & Sightseeing

2 hours

$50
per person

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 person

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