Frequently Asked Questions
The answers provided below are based on answers previously given to customers' questions.
Q: What are the best options for Chicago Sailing Trips?
A: According to verified reviews on Cool Destinations and TripAdvisor, the best Chicago Sailing Trips are:
- Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship
- Educational Tour and Sail Aboard Chicago's Official Flagship Windy 148' Schooner
- Chicago Air & Water Show - Best Seat On The Lake - Tall Ship Windy VIP Cruise
- Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
- Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
Q: What are the best kid-friendly options for Chicago Sailing Trips Tours?
A: According to verified reviews on Cool Destinations and TripAdvisor, the best kid-friendly Chicago Sailing Trips are:
- Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship
- Educational Tour and Sail Aboard Chicago's Official Flagship Windy 148' Schooner
- Chicago Air & Water Show - Best Seat On The Lake - Tall Ship Windy VIP Cruise
- Chicago Skyline Sunset Sail Aboard Official Flagship of Chicago 148' S/V Windy
- Experience Wed & Sat Chicago Fireworks Aboard Tall Ship Windy from Navy Pier
Q: Which Chicago Sailing Trips have Instant Confirmation?
A: Chicago Sailing Trips with Instant Confirmation include:
- Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship
- Educational Tour and Sail Aboard Chicago's Official Flagship Windy 148' Schooner
- Chicago Air & Water Show - Best Seat On The Lake - Tall Ship Windy VIP Cruise
- Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
- Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
View all Tours with Instant Confirmation →
Q: Which Chicago Sailing Trips have Free Cancellation?
A: Chicago Sailing Trips with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:
- Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship
- Educational Tour and Sail Aboard Chicago's Official Flagship Windy 148' Schooner
- Chicago Air & Water Show - Best Seat On The Lake - Tall Ship Windy VIP Cruise
- Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
- Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
View all Tours with Free Cancellation →
Q: Got any more Chicago trip ideas?
A: We sure do. Check out our curated lists of hand-picked Chicago Tours.
- The Top 10 Chicago Tours and Activities of 2023
- Senior-friendly tours, activities and things to do in Chicago
- The best tours and activities for culture lovers in Chicago
- Top Day Trips from Chicago
- Things to do in Chicago this summer
Q: What are the most popular styles of Tours and Activities in Chicago?
A: Based on our sales data over the past year, the most popular styles of tours and activities in Chicago are: