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Chicago
Tours & things to do hand-picked by our insiders

Chicago Architecture River Cruise

838 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 ...  More info

  • Location: Chicago, Illinois
  • Duration: 1 hour 15 minutes (approx.)
From USD $31.75
USD $33.60 Save:USD $1.85

Luxury Overnight Train Journey: Chicago to New Orleans

Enjoy luxury travel with this overnight train service from Chicago to New Orleans. You’ll ride aboard a restored Pullman train car featuring classic, vintage ...  More info

  • Location: Chicago, Illinois
  • Duration: 19.5 hours
From USD $750.00

Chicago CityPass

203 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 ...  More info

  • Location: Chicago, Illinois
  • Duration: Flexible
From USD $96.00

Go Chicago Card

113 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 ...  More info

  • Location: Chicago, Illinois
  • Duration: 1, 2, 3 or 5 days
From USD $84.99

Chicago City Tour and Chicago River Cruise

61 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 ...  More info

  • Location: Chicago, Illinois
  • Duration: 4 hours (approx.)
From USD $58.00

Chicago City Hop-on Hop-off Tour

675 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 ...  More info

  • Location: Chicago, Illinois
  • Duration: Flexible
From USD $34.99

Chicago Explorer Pass

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 ...  More info

  • Location: Chicago, Illinois
  • Duration: Flexible
From USD $92.00

Chicago by Night Helicopter Tour

20 reviews

Watch the Chicago skyline sparkle from the air on this thrilling nighttime helicopter tour! Aboard a heated, state-of-the-art helicopter, soak in amazing views ...  More info

  • Location: Chicago, Illinois
  • Duration: 30 minutes (approx.)
From USD $198.99

Lake Michigan and Chicago River Architecture Cruise by Speedboat

96 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 ...  More info

  • Location: Chicago, Illinois
  • Duration: 75-minutes
From USD $37.06

Chicago Dinner Cruise

30 reviews

Expect the exceptional on this 3-hour premier Chicago dinner cruise experience. Newly renovated, this luxury vessel features a newly furnished rooftop ...  More info

  • Location: Chicago, Illinois
  • Duration: 3 hours (approx.)
From USD $125.99

Blue Man Group at the Briar Street Theater in Chicago

71 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 around ...  More info

  • Location: Chicago, Illinois
  • Duration: 1 hour 45 minutes (approx.)
From USD $53.99
USD $68.99 Save:USD $15.00

Chicago Segway Tour

160 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 ...  More info

  • Location: Chicago, Illinois
  • Duration: 2 or 3 hours
From USD $64.99

Chicago Crime and Mob Tour

111 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 ...  More info

  • Location: Chicago, Illinois
  • Duration: 1 hour 30 minutes (approx.)
From USD $35.95
USD $39.95 Save:USD $4.00

Skydeck Chicago Admission

320 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 ...  More info

  • Location: Chicago, Illinois
  • Duration: Flexible
From USD $19.49

Chicago City Sights Helicopter Tour

16 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 ...  More info

  • Location: Chicago, Illinois
  • Duration: 30 minutes (approx.)
From USD $198.99