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 2400 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 103 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

Viator VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise

4.5 star rating: Recommended 98 Reviews

See classic Chicago sights with this Viator VIP package that includes early entry to the Skydeck in Willis (formerly Sears) Tower where you'll be greeted and ... 

Location: Chicago, Illinois
Duration: 6 hours

From USD $124.00

Chicago Segway Tour

5 star rating: Highly Recommended 209 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

Chicago Crime and Mob Tour

4.5 star rating: Recommended 367 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 CityPASS

5 star rating: Highly Recommended 262 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 $106.00

Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)

3.5 star rating: Worth doing 78 Reviews

Take a tour of Chicago and visit the 360 Chicago (John Hancock Observatory)! This comprehensive half-day tour is the perfect introduction to the Windy City. ... 

Location: Chicago, Illinois
Duration: 4 hours

From USD $65.00

Skydeck Chicago Admission

4.5 star rating: Recommended 583 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

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 43 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 92 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 332 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 130 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
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