All things to do in Chicago

All things to do in Chicago

Tours & things to do hand-picked by our insiders

Top 10 Insider's Picks See all

Chicago CityPass

5 star rating: Highly Recommended 173 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 ...  Read more

Location: Chicago, Illinois
Duration: Flexible

From USD $94.00

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

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 ...  Read more

Location: Chicago, Illinois
Duration: 6 hours (approx.)

From USD $124.99

Chicago City Hop-on Hop-off Tour

4.5 star rating: Recommended 509 Reviews

See all the sights of Chicago at your own pace! On a Chicago City Hop-on Hop-off Tour you can get off the bus at any scheduled stop to visit Chicago's most ...  Read more

Location: Chicago, Illinois
Duration: Flexible

From USD $35.00

Skydeck Chicago Admission

4.5 star rating: Recommended 192 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 ...  Read more

Location: Chicago, Illinois
Duration: Flexible

From USD $18.00

Chicago Architecture River Cruise

5 star rating: Highly Recommended 478 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 ...  Read more

Location: Chicago, Illinois
Duration: 1 hour 15 minutes (approx.)

From USD $31.75

Behind-the-Scenes Chicago Pizza Tour by Coach

4.5 star rating: Recommended 28 Reviews

Get an exclusive view inside four famous Chicago pizzerias on this 3.5-hour tour and enjoy delicious slices at each! With your small group by mini-coach, go ...  Read more

Location: Chicago, Illinois
Duration: 3 hours 30 minutes (approx.)

From USD $60.00

Go Chicago Card

4 star rating: Recommended 85 Reviews

With the Go Chicago™ Card, get access to more than 25 top Chicago attractions, tours and activities all at one low price! Tour the Shedd Aquarium; enjoy fun ...  Read more

Location: Chicago, Illinois
Duration: 1, 2, 3 or 5 days

From USD $79.99

Lake Michigan and Chicago River Architecture Cruise by Speedboat

4.5 star rating: Recommended 69 Reviews

Chicago is renowned for its stunning and original architecture, and the most relaxing way to see it is on a cruise on the Chicago River! You'll learn all ...  Read more

Location: Chicago, Illinois
Duration: 75-minutes

From USD $37.00

Chicago City Sights Helicopter Tour

5 star rating: Highly Recommended 9 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 ...  Read more

Location: Chicago, Illinois
Duration: 30 minutes (approx.)

From USD $198.99

Tommy Gun's Garage Dinner and Show

4.5 star rating: Recommended 94 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 ...  Read more

Location: Chicago, Illinois
Duration: 3 hours (approx.)

From USD $60.00

Chicago Crime and Mob Tour

4 star rating: Recommended 58 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 ...  Read more

Location: Chicago, Illinois
Duration: 1 hour 30 minutes (approx.)

From USD $39.95

Chicago Grand Half-Day Tour

4 star rating: Recommended 151 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 ...  Read more

Location: Chicago, Illinois
Duration: 4 hours (approx.)

From USD $48.00

Chicago City Tour and Chicago River Cruise

4 star rating: Recommended 49 Reviews

Discover Chicago from both land and water on this scenic half-day tour. Take a narrated coach tour through the city’s South Side and see highlights including ...  Read more

Location: Chicago, Illinois
Duration: 4 hours (approx.)

From USD $58.00

Chicago Sunset Dinner Cruise with Buffet

4.5 star rating: Recommended 27 Reviews

Celebrate a night out in Chicago with dinner, dancing and sightseeing aboard a three-hour luxury cruise on Lake Michigan. Glimpse top Chicago attractions like ...  Read more

Location: Chicago, Illinois
Duration: 3 hours (approx.)

From USD $99.14

360 Chicago (formerly John Hancock Observatory) Admission

4.5 star rating: Recommended 39 Reviews

The best views of Chicago can be yours at 360 Chicago (John Hancock Observatory)! Perched 94 stories above the Windy City, the 360 Chicago provides commanding ...  Read more

Location: Chicago, Illinois
Duration: Flexible

From USD $18.00

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