Chicago Sightseeing Tours & Cruises tours

Chicago Sightseeing Tours & Cruises - Page 21

329 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.

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4.45

Chicago Skyline Sail on Tall Ship Windy

From $91

1 provider live

Sail on Chicago's official tall ship

Restroom on board

4.44

Chicago Hop-on Hop-off Bus Tour and 360 CHICAGO Deck

From $84

1 provider live

Explore Chicago's top landmarks on a double-decker bus

48-hour unlimited hop-on hop-off tour access

4.44

Chicago Skyscraper Walking Tour

From $35

2 providers combined

Explore Chicago's architectural evolution

Admission to the Chicago Architecture Center exhibits

4.44

Chicago Architecture Walking Tour

From $35

3 providers combined

Explore iconic Chicago architecture

Certified and professional guide

4.43

Chicago Private City Tour with Hotel Pickup

From $539

1 provider live

Explore Chicago's iconic landmarks

Private transportation

4.43

Chicago Tiki Bar Cruise on the River

From $41

1 provider live

Feel the warmth of a tiki-inspired design

Music

4.42

Chicago Lakefront Bike Tour

From $49

2 providers combined

Feel the wind as you bike along the lakefront

All required equipment (bike and helmet)

4.42

Chicago Street Art Tour

From $40

2 providers combined

Explore vibrant street art in Chicago

Tour guide

4.42

Chicago Lakefront Electric Bike Tour

From $69

1 provider live

Ride along the scenic Lakefront path

Bottled water

4.42

Chicago Fireworks Dinner Cruise on Lake Michigan

$142-$273

3 providers combined

Marvel at Navy Pier's fireworks display

Plated dinner

4.42

Chicago Haunting History Tour

From $64

1 provider live

Explore Chicago's Victorian 'Easy Street'

Restroom on board

4.41

Chicago Private Walking Food Tour

$128-$310

3 providers combined

Savor iconic Chicago deep-dish pizza

Private and exclusive tour