Our Top 10 Insider's Picks in Chicago

Skydeck Chicago Admission

4.5 star rating: Recommended 355 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 $22.00

Chicago Crime and Mob Tour

4.5 star rating: Recommended 168 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: 90 minutes

From USD $35.95
$39.95 Save $4.00

Chicago Dinner Cruise

4.5 star rating: Recommended 35 Reviews

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

Location: Chicago, Illinois
Duration: 3 hours

From USD $96.80
$129.06 Save $32.26

Chicago CityPass

5 star rating: Highly Recommended 209 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 $98.00

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

4 star rating: Recommended 36 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

From USD $124.00

Chicago Grand Half-Day Tour

4 star rating: Recommended 244 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

From USD $47.99

Chicago City Hop-on Hop-off Tour

4.5 star rating: Recommended 721 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

Chicago Architecture River Cruise

5 star rating: Highly Recommended 1020 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 ...  Read more

Location: Chicago, Illinois
Duration: 75 minutes

From USD $33.60
$39.20 Save $5.60

360 Chicago Observation Deck (formerly John Hancock Observatory) Admission

4.5 star rating: Recommended 54 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 $20.00

Chicago Sunset Dinner Cruise with Buffet

4.5 star rating: Recommended 44 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

From USD $104.58

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