Things to do in Chicago

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.

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

$18.00
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

$64.00
per adult

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

$45.00
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

$34.95
per adult

Architecture River Tour by Shoreline Sightseeing
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

$35.56
per adult

Art Deco Skyscrapers: Riverfront Trolley & Walking Tour by the Chicago Architecture Foundation
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

$30.00
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

$23.00
per adult

Arts & Architecture Segway Tour
Equal parts art, architecture—and adventure, this 2-wheeled tour combines Chicago’s finest sights with a convenient and speedy Segway. With your expert guide, glide along the lakefront, see modern art at Millennium Park, and admire the works of master architects like... Read More

Categories: Tours & Sightseeing

2 hours

Free cancellation

$74.12
per adult

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

$63.00
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

$60.00
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

$48.00
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

$72.00
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

$69.00

$54.00
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

$96.00
per adult

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

$39.00
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

$45.50
per adult

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

Categories: Tours & Sightseeing

1 hour 30 minutes

$39.95
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!

$50.00

$25.00
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

$22.67
per adult

Downtown & Skyline Vistas Trolley Tour by the Chicago Architecture Foundation
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

$30.00
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

$172.00
per adult

Evolution of the Skyscraper Walking Tour by the Chicago Architecture Foundaiton
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

$15.00
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

$92.00
per adult

Exploring Old & New Architecture Walking Tour by the Chicago Architecture Foundation
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

$20.00
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

$39.38
per adult

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

$54.45
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

$68.61
per adult

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 360-degree... Read More

$34.74
per adult

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

$120.00
per adult

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

$120.00
per adult

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

$95.00
per adult

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

$95.00
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

$20.00
per adult

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

$35.00
per adult

Italian Food 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!

$50.00

$25.00
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

30 minutes

Free cancellation

$19.08
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

$45.50
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

$27.78
per adult

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

$15.00
per adult

LEGOLAND® Discovery Center Chicago
LEGO® bricks come to life at the LEGOLAND® Discovery Center. Let your imagination run wild as you build amazing creations, learn top tips from the Master Model Builders, ride the Technicycle, and sit down for a unique 4-D cinema... Read More

Categories: Attractions

1 day

Free cancellation

$18.90
per adult

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

$42.00
per adult

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

$50.00
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

$64.65
per adult

Millennium Park: Beyond the Bean Walking Tour by the Chicago Architecture Foundation
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

$20.00
per adult

Modern Skyscrapers Walking Tour by the Chicago Architecture Foundation
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

$20.00
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

$74.12
per adult

Museums & Parks Sunset Bike Tour
Your bicycle tour begins with a journey through the local neighborhoods of Gold Coast, Lincoln Park, and Wrigleyville. Ride along the lakefront visiting parks and gardens as the refreshing lake breeze races across your face and the sound of waves... Read More

Categories: Land Adventures, Tours & Sightseeing

2 hours

Free cancellation

$37.00
per adult

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

$146.74
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

$205.74
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

$39.38
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

$26.00
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

$31.00
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

$40.00
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, Tours & Sightseeing

3 hours

Free cancellation

$45.00
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

$50.00
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

$126.34
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 buffs... Read More

Categories: Attractions

5 hours

$23.00
per adult

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

$50.00
per adult

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