A sailboat with teak decking, dual steering wheels, and stainless railings on open water at Windy City Sailing.
A boat lounge with wood-paneled walls, skylights, cushioned seating, and a table set for snacks at Windy City Sailing.
A white sailing boat with guests relaxing on the deck, gliding on open water at Windy City Sailing.
A boat with cushioned bench seating, wood paneling, and a table topped with stacked red cups at Windy City Sailing.

Windy City Sailing

Boat

#48 of 290 Birthday Party venues in Chicago
#28 of 267 40th Birthday Party venues in Chicago
400 West Belmont Harbor Drive, Chicago, IL 60657 –
Lakeview, Chicago, IL
From $200
hire fee
Up to 8
seats
Up to 10
standing
Venue doesn't offer catering
Parking available
Manager's avatar
Edwina NA
Your Personal Event Manager from Windy City Sailing
Response rate: 100%
Response time: Within 3 hours
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Partnered with Tagvenue for 3 years
This manager has been a trusted partner of Tagvenue, consistently recognised by customers for their reliability.
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Venue overview

Private sailing charters along Chicago's lakefront offer stunning views of Navy Pier and the city skyline. Perfect for group celebrations, with your own music and a PA system onboard.

This is an AI-generated summary based on client reviews and venue profile

Spaces for hire at Windy City Sailing

Entire Venue at Windy City Sailing
Entire Venue
Boat
·
Whole venue
8 seats
10 standing
Experience an unforgettable time on our beautiful sailsboat. With up-to-date amenities and two bathrooms onboard, we assure the comfort of all our guests. Our yachts are professionally maintained and equipped. In addition, we certify, train and employ United States Coast Guard Captains with over 20 years of experience.
Natural light
Flatscreen TV
PA system / music speakers
Play your own music
from $200 hire fee
Enquire now

Prices and opening hours

Sunday
9:00 am – 5:00 pm
from $200 hire fee per hour
Entire Venue
9:00 am – 5:00 pm
from $200 hire fee per hour
Monday
9:00 am – 5:00 pm
from $200 hire fee per hour
Entire Venue
9:00 am – 5:00 pm
from $200 hire fee per hour
Tuesday
9:00 am – 5:00 pm
from $200 hire fee per hour
Entire Venue
9:00 am – 5:00 pm
from $200 hire fee per hour
Wednesday
9:00 am – 5:00 pm
from $200 hire fee per hour
Entire Venue
9:00 am – 5:00 pm
from $200 hire fee per hour
Thursday
9:00 am – 5:00 pm
from $200 hire fee per hour
Entire Venue
9:00 am – 5:00 pm
from $200 hire fee per hour
Friday
9:00 am – 5:00 pm
from $200 hire fee per hour
Entire Venue
9:00 am – 5:00 pm
from $200 hire fee per hour
Saturday
9:00 am – 5:00 pm
from $200 hire fee per hour
Entire Venue
9:00 am – 5:00 pm
from $200 hire fee per hour

Best Price guarantee: you will always pay the same price as booking directly with the venue, and we never add hidden or processing fees.

Facilities and catering options

Up to 10
standing
Up to 8
seats
External catering allowed
Parking available
BYO alcohol
Unavailable: In-house catering
Unavailable: Accommodation available
Unavailable: Promoted / ticketed events
Unavailable: Alcohol provided

About Windy City Sailing

Windy City Sailing is a Tagvenue Partner. This business has registered with Tagvenue and agreed to our venue partner standards.

Windy City Sailing is a private yacht and sailing charter operator that specializes in small-group, captain-led and bareboat recreational charters.

Venue highlights: Windy City Sailing offers captain-led private yacht charters and bareboat hire, letting hosts choose between a crewed cruise or a self-skippered option. The fleet has open decks and comfortable interiors arranged for socialising and waterside sightseeing, and boats are adaptable for small-group events. Private sailings can be tailored for occasions such as sunset cruises or fireworks-viewing.

Best for: Sightseeing and fireworks-view cruises, family outings and small-group celebrations, and corporate client entertaining or team-building on the water.

Location: Belmont Harbor is a marina-front neighborhood beside moorings and lakefront parkland that provides direct access to open water. The neighborhood has nearby restaurants and bars suitable for post-cruise gatherings.

What guests say: The crew are professional, knowledgeable and consistently focused on safety during private charters. The boats are clean, well-presented and arranged to maximize deckside sightseeing and comfortable socializing.

www.windycitysailing.com •
+1 773-868-0096

FAQ

You are welcome to bring aboard food and drink of your choice.

Cancellations 60 days in advance will receive a full refund.

Cancellations 60 days to 30 days in advance will receive a 50% refund.

Cancellations for events starting within 30 days are non-refundable.

At Windy City Sailing, the following catering options are available:

  • Bringing your own catering/food is allowed
  • Bringing your own alcohol is allowed

  • Paid parking facilities are available nearby

Windy City Sailing is located at 400 West Belmont Harbor Drive, in Lakeview, Chicago, IL.

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Explore other spaces in the area

400 West Belmont Harbor Drive, Chicago, IL 60657
Public transportation
Parking
Hotels
Public transportation
  • Subway Addison 0.8 mi
  • Subway Belmont 0.9 mi
  • Subway Wellington 1.1 mi
  • Bus Halsted & Waveland/Broadway Terminal 0.7 mi
  • Bus Belmont & Halsted Terminal 0.7 mi
  • Bus St. Joseph Hospital 0.8 mi
Parking
  • Parking Belmont Harbor North Lot - Parking lot, W Belmont Harbor Dr, Chicago 0.1 mi
  • Parking 3270 N Lake Shore Dr Parking - 3270 N Lake Shore Dr, Chicago 0.3 mi
Hotels
  • Majestic Hotel 0.4 mi
  • Best Western Plus Hawthorne Terrace Hotel 0.5 mi

Windy City Sailing is popular for

Party Holiday Party Birthday Party Outdoor Space Corporate Event Engagement Party Meeting

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United States > Chicago > Windy City Sailing