Chicago Sightseeing Tours & Cruises tours

Chicago Sightseeing Tours & Cruises - Page 4

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.

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4.57

Chicago Brunch Cruise on Lake Michigan

From $157

1 provider live

Savor a delicious brunch buffet

Unlimited coffee, hot tea, and iced tea

4.57

Chicago River Dinner Cruise with Fireworks

From $335

1 provider live

Savor a delicious plated dinner

Delicious plated dinner with freshly prepared entrees, salads, and desserts

4.57

Chicago Riverwalk Architecture Walking Tour

From $49

1 provider live

Explore Chicago's iconic skyline

Live, in person tour guide

4.57

Chicago Boat Tour at Sunset

From $1600

1 provider live

Cruise past iconic Navy Pier

WiFi on board

4.57

Chicago Fashion Outlets Private Shopping Tour

From $270

1 provider live

Explore luxury boutiques

Private transportation

4.57

Chicago Union Station Movie and TV Walking Tour 90 Min

From $50

1 provider live

Explore iconic film locations

Visual and audio media to enhance your tour experience

4.57

Chicago Evening Cruise on Lake Michigan

From $46

1 provider live

Embark on a relaxing evening cruise

One drink ticket

4.57

Chicago History and Evolution Walking Tour

From $118

1 provider live

Uncover Chicago's vibrant history

Professional and experienced tour guide

4.57

Chicago Sedan Sightseeing Tour 4 hr

From $250

1 provider live

Experience luxury in a private sedan

Private transportation

4.57

Chicago Pedicab Tour with Music 1 hr

From $80

1 provider live

Enjoy a relaxing ride with your favorite music

Private pedicab tour of Chicago

4.57

Chicago Private Tour

From $300

1 provider live

Explore iconic Chicago landmarks

Guide languages in English and Spanish

4.57

Chicago Blues Concert Aboard Tall Ship

From $81

1 provider live

Sail on the iconic Tall Ship Windy

Access to all ship amenities (restrooms, bar, seating areas)