Things to do in Chicago, Illinois (IL): The Best Boat Rentals

October 8, 2021 Florencio Paulino

The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.
Restaurants in Chicago

1. Windy City Sailing

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5.0 based on 52 reviews

Windy City Sailing

Windy City Sailing provides World-Class sailing and power yacht charters for recreational, romantic and educational experiences to individuals and small groups of up to 10 people. Experience the thrill of sailing and Chicago sightseeing with United States Coast Guard certified captains on our custom yachts. Our charters are personal and private for your group, family or clients.

2. Knot My Boat Charters

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5.0 based on 1 reviews

Knot My Boat Charters

Knot My Boat Charters is a Chicago-based company that specializes in providing our clients with luxurious, yet affordable, boat charters and event accommodations. We provide expertise gathered from 12 years of captaining and 16 years of combined hospitality experience in Chicago. Our team prides itself in providing an exceptional full-service experience to all of our clients.

3. Chicago Sailing

Excellent
60%
Good
10%
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Terrible
30%
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3.5 based on 10 reviews

Chicago Sailing

Chicago Sailing is proud to be Chicago's premier public sailing facility! With a fleet of over 23 sailboats ranging from 22'-53' we offer sailing lessons, captained charters, and rentals. Chicago Sailing is a US Sailing certified school and teaches to the highest standards in sailing. Group and teambuilding events are also available upon request, we regularly handle groups of up to 60 people.

4. Chicago Sailboat Charters

Excellent
87%
Good
13%
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5.0 based on 15 reviews

Chicago Sailboat Charters

5. Chicago River Canoe & Kayak

Excellent
63%
Good
38%
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4.5 based on 8 reviews

Chicago River Canoe & Kayak

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