What types of sailing charters does Windy City Sailing offer?

Windy City Sailing offers both private sailing yacht charters and bareboat charters along the Chicago Lakefront and Navy Pier. Customers can choose from charters with a captain and crew for groups up to six, or a bareboat charter for groups up to ten with a USCG licensed captain paid separately.

What is the minimum booking for a sailing charter?

All private Chicago sailboat charters have a three-hour minimum. However, charter extensions are available upon request if guests wish to extend their sailing experience.

Can customers bring their own food and drinks?

Yes, Windy City Sailing encourages customers to bring their own food and refreshments, including alcoholic beverages, to enjoy during the sailing charters.

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Windy City Sailing

$900.0K revenue • 6 employees • 400 W Belmont Harbor Dr, Chicago, IL, 60657, United States

Last Updated Feb 16, 2026

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Company Overview

Company Name

Windy City Sailing

Address

400 W Belmont Harbor Dr, Chicago, IL, 60657, United States

Website

windycitysailing.com

Phone

(773) 868-0096

Approx. Annual Revenue

$0.9M

Employees

Established

2003

Google Reviews

5.0 (35 reviews)

About Windy City Sailing

Windy City Sailing is a Chicago-based company that offers private sailing yacht charters and bareboat charters along the Chicago Lakefront and Navy Pier. They provide a range of sailing experiences, from charters with a captain and crew to bareboat charters for groups up to ten people. The company is known for its well-maintained and equipped yachts, as well as its experienced and certified USCG captains.

Business Profile

Read from the Windy City Sailing website on Oct 13, 2026. Hover an item to see the exact wording it came from.

How Windy City Sailing works

Online bookingⓘ

About the website

Website quality (AI-assessed): 8/10 · Current copyright 2026; Detailed FAQs and policies

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Windy City Sailing

Company Overview

Company Name

Address

Website

Phone

Approx. Annual Revenue

Employees

Established

Google Reviews

About Windy City Sailing

Business Profile

How Windy City Sailing works

About the website

Boat Charters & Tours Companies near Chicago, IL

Frequently Asked Questions about Windy City Sailing

What types of sailing charters does Windy City Sailing offer?

What is the minimum booking for a sailing charter?

Can customers bring their own food and drinks?

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