Chicago Sightseeing Tours & Cruises tours

Chicago Sightseeing Tours & Cruises - Page 2

84 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:

4.58

Chicago Walking Tour with Free Bike or Kayak Rental

From $45

Explore Millennium Park's iconic art

Local, professional guide

4.58

Chicago River Architecture Tour

From $29

Discover the Wrigley Building’s dazzling towers

Boat equipped with restroom and air conditioning

4.58

Chicago Scenic Driving Tour

From $315

Explore iconic Chicago landmarks

Hotel pickup and drop-off

4.57

Chicago Food, History & Architecture Walking Tour

$99-$101

Savor deep-dish pizza and Italian beef

Guided walking tour through downtown Chicago

4.57

Chicago Fire TV Show Set Tour

From $315

Step into the world of Firehouse 51

Private transportation

4.57

Chicago Walking Tour: Modern Architecture

From $35

Explore iconic Mid-Century Modern architecture

Admission to the Chicago Architecture Center

4.57

Chicago LGBTQ+ History Bus Tour

$43-$50

Uncover Chicago's LGBTQ+ history

Private transportation

4.56

Chicago Architecture and Engineering Walking Tour

$30-$35

Explore Chicago's iconic buildings

Expert guide trained as an engineer

4.56

Chicago African American Heritage Tour

From $125

Explore historic Bronzeville

Air-conditioned vehicle

4.56

Chicago Westside Food Tasting Bike Tour

From $99

Taste diverse ethnic cuisines

Four-hour bike tour

4.56

Chicago Lake Michigan Boat Tour

$60-$61

Feel the wind as you speed across Lake Michigan

Life jackets

4.55

Chicago Downtown Guided Walking Tour

$49-$52

Explore iconic public art by Picasso and Chagall

Wheelchair friendly