Chicago Sightseeing Tours & Cruises tours

Chicago Sightseeing Tours & Cruises - Page 3

270 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 Shopping & Fashion 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 History Museum Private Tour

From $163

1 provider live

Explore Chicago's vibrant past

Admission fee

4.58

Chicago Helicopter Tour at Sunset 45 Min

$751-$849

2 providers combined

Create lasting memories with a bucket list experience

Noise-canceling headsets

4.58

Chicago Haunted History and Ghost Hunt Tour

From $32

1 provider live

Explore Chicago's Millionaire's Row

Ghost hunting gear including EMF meters, dowsing rods, and spirit boxes

4.58

Chicago Walking Tour of the Loop

From $65

1 provider live

Explore iconic skyscrapers

Transit tickets

4.58

Chicago Historic Homes and Cottages Walking Tour

From $45

1 provider live

Explore Wicker Park's charming streets

Historical photos on a private web page

4.58

Chicago Workers Cottages Walking Tour

$40-$45

2 providers combined

Explore the Oldtown Triangle

Historical photos of each stop in a free app

4.58

Chicago Walking Tour with Free Bike or Kayak Rental

From $45

2 providers combined

Explore Millennium Park's iconic art

Local, professional guide

4.58

Chicago Scenic Driving Tour

From $315

2 providers combined

Enjoy a comfortable ride exploring iconic landmarks

Bottled water

4.57

Chicago Al Capone Gangster Tour 3 hr

From $880

1 provider live

Visit historic gangster sites

Hotel pickup and drop-off within Chicago city limits

4.57

Chicago Private Sunset Sail on Lake Michigan

From $508

1 provider live

Sail along Chicago's stunning lakefront

Use of Bluetooth speakers

4.57

Chicago Segway Tour of Landmarks and Ghosts

$64-$78

2 providers combined

Glide through Grant Park's fragrant paths

Professional guide

4.57

Chicago Shopping Tour to Premium Outlets

From $297

1 provider live

Explore luxury boutiques

Private transportation