Chicago Sightseeing Tours & Cruises

132 experiences to discover

Air & Helicopter Tours City & Sightseeing Tours Cruises & Sailing Tours Cultural & Theme Tours Day Trips & Excursions Multi-Day & Extended Tours 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.

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4.66

Chicago Architecture and True Crime Tour

From $35

2 providers combined

Explore Chicago's iconic architecture

History Buff & True Crime Nerd Guide

4.64

Chicago Lakefront Segway Tour

$68-$70

2 providers combined

Glide through scenic Grant Park

Certified Segway tour guide

4.64

Chicago Architecture River Cruise

From $39

2 providers combined

Cruise along all three branches of the Chicago River

Architecture river cruise

4.62

Chicago Architecture Interiors Tour

From $35

2 providers combined

Marvel at the world's largest Tiffany dome

Local guide

4.61

Chicago Architecture Walking Tour

From $35

2 providers combined

Explore Chicago's elevated train platforms

Walking tour

4.61

Chicago Food and Walking Tour

From $85

2 providers combined

Savor iconic Chicago bites

Deep dish pizza slice

4.6

Chicago Lakefront Neighborhoods Bike Tour

$55-$59

2 providers combined

Ride along Chicago's scenic Lakefront Trail

Bicycle

4.6

Chicago River Architecture Tour

From $29

2 providers combined

Discover Chicago's iconic skyline

Boat equipped with restroom and air conditioning

4.59

Chicago Architecture and Engineering Walking Tour

$30-$35

2 providers combined

Explore Chicago's iconic buildings

Expert guide trained as an engineer

4.59

Chicago TV Show Set Tour

From $315

2 providers combined

Step into the world of Firehouse 51

Pickup and drop-off from within 5 miles of downtown Chicago

4.59

Chicago Historic Homes and Cottages Walking Tour

From $45

1 provider live

Explore charming Wicker Park

Historical photos on a private web page

4.58

Chicago Workers Cottages Walking Tour

$40-$45

2 providers combined

Discover the resilient spirit of Chicago

Historical photos of each stop in a free app