All things to do in Chicago

All things to do in Chicago

Tours & things to do hand-picked by our insiders

From USD $24.00
From USD $37.95
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Chicago Architecture River Cruise

5 star rating: Highly Recommended 2378 Reviews

Experience one of the world’s most beautiful cities on a 75-minute cruise on the historic Chicago River. On this architecture cruise, head down the main branch ... 

Location: Chicago, Illinois
Duration: 75 minutes

From USD $43.68

Chicago Prohibition Tour

5 star rating: Highly Recommended 98 Reviews

Discover the underground world of the Prohibition-era speakeasy on an entertaining adults-only tour that takes you to four historic Chicago bars. Learn why the ... 

Location: Chicago, Illinois
Duration: 3 hours 30 minutes

From USD $45.00

Chicago Crime and Mob Tour

4.5 star rating: Recommended 362 Reviews

Some of the world’s most notorious criminals, mobsters and gangsters bamboozled their way through Chicago. On this Chicago crime tour, escape into the city’s ... 

Location: Chicago, Illinois
Duration: 90 minutes

From USD $37.95

Chicago Segway Tour

5 star rating: Highly Recommended 208 Reviews

Hop on the most innovative tour to hit Chicago in years! Gliding around the Windy City on your very own Segway, you'll see all the famous sights - Buckingham ... 

Location: Chicago, Illinois
Duration: Flexible

From USD $70.85

Skydeck Chicago Admission

4.5 star rating: Recommended 579 Reviews

Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest ... 

Location: Chicago, Illinois
Duration: Flexible

From USD $24.00

Chicago CityPASS

5 star rating: Highly Recommended 261 Reviews

Chicago CityPASS is the best deal in the Windy City, giving you discounted admission to five of the city's premier attractions. The Chicago CityPASS ensures ... 

Location: Chicago, Illinois
Duration: Flexible

From USD $99.75

Chicago City Hop-on Hop-off Tour

4.5 star rating: Recommended 908 Reviews

Explore Chicago at your own pace during this hop-on hop-off bus trolley of the city. Choose between a 1-, 2-, or 3-day pass depending on your trip time. See ... 

Location: Chicago, Illinois
Duration: Flexible

From USD $30.99

Tommy Gun's Garage Dinner and Show

5 star rating: Highly Recommended 153 Reviews

Welcome to the only speakeasy dinner show in Chicago Tommy Gun's Garage! Just say the password and you'll be transported back to the roaring twenties. You'll ... 

Location: Chicago, Illinois
Duration: 3 hours

From USD $67.00

Chicago Style Food Tour

5 star rating: Highly Recommended 40 Reviews

Confused on what to see and do while in Chicago? It goes without saying that the Windy City has it all; from food, history, architecture, culture and beyond. ... 

Location: Chicago, Illinois
Duration: 3 hours

From USD $55.00

Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour

5 star rating: Highly Recommended 88 Reviews

Get an in-depth look at Chicago Loop architecture on a walking tour that takes you inside landmark buildings in the design-rich city. Appreciate the interiors ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $26.00

Chicago Grand Half-Day Tour

4 star rating: Recommended 329 Reviews

This comprehensive half-day tour of Chicago is the perfect introduction to the Windy City! Discover the highlights of Chicago’s North Side and South Side and ... 

Location: Chicago, Illinois
Duration: 4 hours

From USD $48.00

Chicago Architectural River Cruise

5 star rating: Highly Recommended 129 Reviews

Take in the views on this 90-minute Architectural Tour, a jaw-dropping excursion through a city that defied all expectations … even the laws of gravity.

Location: Chicago, Illinois
Duration: 90 minutes

From USD $48.16

Chicago City Sights Helicopter Tour

5 star rating: Highly Recommended 26 Reviews

Experience all of Chicago’s best sights from the air on this exciting helicopter tour! Aboard a state-of-the-art helicopter, you'll enjoy a magnificent view of ... 

Location: Chicago, Illinois
Duration: 15 minutes

From USD $149.00

Willis Tower Skydeck Dinner

4.5 star rating: Recommended 20 Reviews

Enjoy a VIP dinner at Chicago’s Skydeck where you get breathtaking views of the city. Located in the Willis Tower, the Skydeck perches 1,353 feet (412 meters). ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $117.65

Blue Man Group at the Briar Street Theater in Chicago

5 star rating: Highly Recommended 100 Reviews

See the Blue Man Group, one of Chicago's longest running shows, at the Briar Street Theater in downtown Chicago. The phenomenon that has visited cities ... 

Location: Chicago, Illinois
Duration: 105 minutes

From USD $69.60
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