Chicago Sightseeing Tours & Cruises

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.

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4.63

Chicago Architecture Walking Tour

From $35

Explore Chicago's newest architectural marvels

Admission to the galleries of the Chicago Architecture Center

4.62

Chicago Walking Tour

From $44

Step into Chicago's vibrant history

Top tier 5-star rated professional guide

4.6

Chicago Architecture and Engineering Walking Tour

From $35

Explore iconic Chicago buildings

Expert guide trained as an engineer

4.6

Chicago River Architecture Tour

From $39

Discover the Wrigley Building’s history

Boat equipped with restroom and air conditioning

4.59

Chicago Architectural Interiors Tour

From $35

Marvel at Tiffany stained glass mosaics

All necessary entrance fees

4.58

Chicago Downtown Loop & Millennium Park Walking Tour

From $49

Explore Chicago's vibrant Loop area

Professional tour guide

4.58

Chicago West Side Foodie Bike Tour

$99-$100

Taste authentic Chicago dishes

Local guide

4.58

Chicago Lake Michigan Sightseeing Boat Tour

From $60

Feel the wind as you speed across Lake Michigan

1-hour Lake Michigan tour

4.57

Chicago Instagram Car Tour

From $750

Feast your eyes on iconic murals

All Fees and Taxes

4.57

Chicago LGBTQ+ History Bus Tour

From $50

Uncover Chicago's LGBTQ+ history

Private transportation

4.56

Chicago Lakefront Neighborhoods Bike Tour

$55-$60

Immerse in Chicago's vibrant neighborhoods

Bicycle

4.56

Chicago Ghosts & Haunted History Walking Tour

From $49

Begin an eerie adventure at Congress Hotel

Professional, local tour guide