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

From USD $31.75
$33.60 Save $1.85

Chicago CityPass

5 star rating: Highly Recommended 195 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 $96.00

Chicago Architecture River Cruise

5 star rating: Highly Recommended 822 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
$33.60 Save $1.85

Chicago City Hop-on Hop-off Tour

4.5 star rating: Recommended 657 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 $34.99

Skydeck Chicago Admission

4.5 star rating: Recommended 301 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 $19.49

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

4 star rating: Recommended 25 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 ...  Read more

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

From USD $124.00

Behind-the-Scenes Chicago Pizza Tour by Coach

5 star rating: Highly Recommended 47 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 $59.99

Go Chicago Card

4.5 star rating: Recommended 107 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 $84.99

Chicago Segway Tour

5 star rating: Highly Recommended 156 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 ...  Read more

Location: Chicago, Illinois
Duration: 2 or 3 hours

From USD $64.99

Chicago City Sights Helicopter Tour

5 star rating: Highly Recommended 14 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

5 star rating: Highly Recommended 106 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 $64.99

Lake Michigan and Chicago River Architecture Cruise by Speedboat

4.5 star rating: Recommended 94 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 $37.06

Chicago Grand Half-Day Tour

4 star rating: Recommended 203 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 $47.99

Chicago Explorer Pass

5 star rating: Highly Recommended 3 Reviews

Create your own sightseeing itinerary with the Chicago Explorer Pass, saving up to 42% on ticket prices. This multi-attraction pass, valid for 30 days after ...  Read more

Location: Chicago, Illinois
Duration: Flexible

From USD $92.00

Chicago Sunset Dinner Cruise with Buffet

4.5 star rating: Recommended 37 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 $101.49

360 Chicago (formerly John Hancock Observatory) Admission

4.5 star rating: Recommended 50 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 $18.99
Insider's Guide to Chicago

Major attractions, tips and our top things to see and do.

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