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.

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4.58

Chicago Scenic Driving Tour

From $315

Explore iconic Chicago landmarks

Hotel pickup and drop-off

4.58

Chicago Lake Michigan Boat Tour

$60-$61

Feel the wind as you speed across Lake Michigan

Life jackets

4.57

Chicago Ghost Tour: Wind and Souls Adults Only

From $35

Feel your spine tingle with ghostly tales

A spooky and historically accurate tour with a local guide

4.57

Chicago Lakefront Segway Tour

$64-$76

Glide past Buckingham Fountain's water show

Certified Segway tour guide

4.57

Chicago Art Walking Tour

From $52

Explore Chicago's iconic public art

Wheelchair friendly

4.57

Chicago LGBTQ+ History Bus Tour

$43-$50

Uncover Chicago's LGBTQ+ history

Private transportation

4.56

Chicago City Tour with Instagram Highlights 6 hr

$750-$999

Explore iconic Chicago landmarks

Bottled water

4.56

Chicago Architecture and Engineering Walking Tour

$30-$35

Explore Chicago's iconic buildings

Expert guide trained as an engineer

4.56

Chicago Fireboat River & Lake Cruise

$47-$57

Cruise on a historic Chicago fireboat

Bathrooms available onboard

4.56

Chicago Skyline Helicopter Tour

$751-$849

Create lasting memories with a bucket-list experience

Noise-canceling headsets

4.56

Chicago Loop Walking Tour

From $60

Immerse yourself in Chicago's vibrant heart

Local guide

4.55

Chicago Prohibition and Architecture Walking Tour

$49-$50

Explore Chicago's Prohibition history

Guided walking tour through downtown Chicago