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Sailing Tours & Experiences in Chicago
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Great40+ bookedSailing | Sunset & NightChicago: Tall Ship Windy Architecture & Skyline Sailing Tour
- 75 minutes • Guiding available
From$49.99 /person -
Excellent10+ bookedSailing | DaytimeChicago: Lake Michigan Educational 'Tall Ship Windy' Cruise
- 1.5 hours • Guiding available
From$29.00 /person -
NEWBook nowSailing | Daytime | Sunset & NightChicago: Private Catamaran Sailing for up to 12 people
- 2-4 hours • Private tour • Guiding available
From$1,500.00 /group
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Frequently Asked Questions
1. What are the best Architecture Cruises & Boat Tours in Chicago?
Based on popularity and guest reviews, the best Architecture Cruises & Boat Tours in Chicago are:
- Chicago River: 1.5-Hour Guided Architecture Cruise
- Chicago: Architecture River Cruise Skip-the-Ticket Line
- Chicago: 1.5-Hour Lake and River Architecture Cruise
- Chicago: 45-Minute Family-Friendly Architecture River Cruise
- Chicago: Architecture Boat Tour with Drinks
- Chicago: 1.5-Hour Scenic Sunset Lake Cruise
- Chicago: Architecture Center Cruise on Chicago's First Lady
- Chicago: Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
- Chicago: Fireworks Cruise with Lake or River Viewing Options
- Chicago: Lake Michigan Skyline Cruise
2. What are the top Speed Boats in Chicago?
Based on popularity and guest reviews, the top Speed Boats in Chicago are:
3. What are the most popular Chicago Sunset and Night Cruises & Boat Tours?
Based on popularity and guest reviews, the most popular Chicago Sunset and Night Cruises & Boat Tours are:
- Chicago River: 1.5-Hour Guided Architecture Cruise
- Chicago: Architecture River Cruise Skip-the-Ticket Line
- Chicago: 1.5-Hour Lake and River Architecture Cruise
- Chicago: 45-Minute Family-Friendly Architecture River Cruise
- Chicago: 1.5-Hour Scenic Sunset Lake Cruise
- Chicago: Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
- Chicago: Fireworks Cruise with Lake or River Viewing Options
- Chicago: Lake Michigan Buffet Brunch, Lunch or Dinner Cruise
- Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour
- Chicago: Fireworks Buffet Dinner Cruise on Lake Michigan
4. What are the best Chicago Dinner Cruises?