Chicago Sightseeing Tours & Cruises tours

Chicago Sightseeing Tours & Cruises - Page 6

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 Dinner Cruise on Lake Michigan

From $159

1 provider live

Savor a delicious plated dinner

Unlimited coffee, hot tea, and iced tea

4.57

Chicago River Plated Dinner Cruise

From $208

1 provider live

Savor a delicious plated dinner

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

4.57

Chicago Wicker Park Architecture Walking Tour

From $40

1 provider live

Discover architectural marvels of Wicker Park

Guided walking tour of Wicker Park

4.57

Chicago Downtown Private Walking Tour

From $205

1 provider live

Explore iconic landmarks like Cloud Gate

Private Walking Tour of Downtown Chicago’s Iconic Landmarks and Hidden Gems

4.57

Chicago Fashion Designers Shopping Tour with Stylist

From $153

1 provider live

Explore Chicago's fashion scene

Personalized local fashion boutiques circuit

4.57

Chicago Photoshoot Experience

From $250

1 provider live

Capture iconic Chicago landmarks

Personal Travel Photographer

4.57

Chicago River Yoga Walk Tour 90 min

From $44

1 provider live

Experience yoga along the scenic Chicago River

Live, in person Yoga Instructor/Tour Guide

4.57

Detroit to Cleveland Multi-City Tour 5 Days

From $1191

1 provider live

Explore Detroit's Motor City heritage

Admission to Toronto Sightseeing Harbour Tour, Skylon Tower, and lunch (if selected)

4.57

Chicago Loop Neighborhood Walking Tour

From $60

1 provider live

Immerse in Chicago's vibrant Loop

Local Guide

4.57

Chicago Sailboat Charter with Captain 3 hr

From $719

1 provider live

Sail along the Chicago Lakefront

USCG-Certified Captain trained in First Aid and CPR

4.57

Chicago Galena Historic Sites and River Views Day Tour

From $126

1 provider live

Explore historic Galena

Ulysses S. Grant Home (if price option selected)

4.57

Chicago Skyscraper Evolution Tour in French

From $35

1 provider live

Explore Chicago's architectural history

Free for Chicago Architecture Center members