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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4.62

Chicago Architecture Walking Tour

$35-$36

Explore Chicago's elevated train system

Walking tour

4.6

Chicago History and Mystery Walking Tour

$29-$33

Discover Chicago's hidden stories and secrets

All fees and taxes

4.58

Chicago Architecture and Engineering Walking Tour

$30-$35

Explore iconic Chicago buildings

Expert guide trained as an engineer

4.58

Chicago Downtown Loop & Millennium Park Walking Tour

$43-$49

Explore the vibrant Loop area

2 Hour Walking Tour

4.58

Chicago Lakefront Neighborhoods Bike Tour

$53-$55

Immerse in Chicago's vibrant neighborhoods

Bicycle

4.58

Chicago Ghosts & Haunted History Walking Tour 2 hr

$35-$49

Begin an eerie adventure at Congress Hotel

Professional, local tour guide

4.58

Chicago Lake Michigan Sightseeing Boat Tour

$54-$60

Feel the wind in your hair on a speedboat

Life jackets

4.57

Chicago Lakefront & Museum Campus Segway Tour

$67-$70

Glide through Grant Park's garden paths

Professional guide

4.57

Chicago River Architecture Tour

From $49

Discover iconic Chicago landmarks

Guided 2-hour walk along Chicago's Riverwalk

4.57

Chicago LGBTQ+ History Bus Tour

$43-$50

Uncover Chicago's LGBTQ+ history

Private transportation

4.56

Chicago Walking Tour with Bike or Kayak Rental

From $45

Explore Chicago's iconic landmarks

Historical stories about Chicago's past

4.56

Chicago Black Heritage Tour

$111-$125

Explore historic Bronzeville

Air-conditioned vehicle