Chicago Sightseeing Tours & Cruises tours

Chicago Sightseeing Tours & Cruises - Page 3

68 experiences to discover

Air & Helicopter Tours City & Sightseeing Tours Cruises & Sailing Tours Cultural & Theme Tours Day Trips & Excursions Private & Custom Tours Walking & Biking Tours

Explore the best sightseeing tours & cruises tours and activities in Chicago. Our unbiased ratings help you find the perfect experiences for your trip.

Sort by:

4.48

Chicago Food Walking Tour with Bike or Kayak Rental

$80-$85

Savor Chicago-style deep-dish pizza

Walking tour

4.47

Chicago Fulton Market Donut Adventure 2 hr

$65-$68

Sample Chicago's finest donuts

Donuts!

4.47

Chicago Downtown Food and Sightseeing Bike Tour

From $60

Taste iconic Chicago foods like deep-dish pizza

Food & snacks

4.46

Chicago Bikes, Bites, and Brews Tour

From $89

Savor deep dish pizza and gourmet brownies

Expert local guide

4.46

Chicago Skyscraper Walking Tour

From $35

Explore Chicago's architectural evolution

Admission to the Chicago Architecture Center Exhibits

4.46

Chicago Walking Tour: Magnificent Mile

$30-$35

Discover the transformation from Pine Street to Magnificent Mile

Admission to the Galleries of the Chicago Architecture Center

4.45

Chicago Walking Tour with Mobile App

$15-$17

Explore Chicago's iconic landmarks

Full flexibility: start at any hour, take a break at any time and resume later

4.44

Chicago Private Custom Walking Tour

$110-$127

Explore Chicago with a local guide

Private walking tour

4.41

Chicago Prohibition-Era Walking Tour

From $50

Explore Prohibition-era architecture

Local English-speaking guide

4.41

Chicago Food, History, and Architecture Tour

From $86

Explore Chicago's iconic Pedway

Walking tour

4.39

Chicago River Brunch Cruise

$103-$110

Savor a chef-prepared brunch

2-hour cruise

4.38

Chicago Street Art Tour

From $40

Discover vibrant street art

Walking tour of Wicker Park, Bucktown, and Logan Square