Two Brothers Sailing Adventures

Chicago Private Boat Charters & Events

Chicago Boat Chartersfor Events and Special Occasions

Plan a private Lake Michigan sailing experience for birthdays, bachelorette and bachelor parties, date nights, proposals, corporate outings, holiday weekends, and Chicago summer events.

Private charters from Montrose Harbor. BYOB-friendly. Restroom onboard.

U.S. Navy Blue Angels jets in formation with smoke trails against a blue sky—Chicago Air and Water Show atmosphere
Lake Michigan - Chicago

Not Sure Which Charter Fits Your Event?

Use these quick recommendations to choose the right experience for your group.

Good to know

Events, routes, and timing may vary based on weather, lake conditions, lake traffic, holiday demand, and captain discretion. For high-demand weekends and major Chicago events, booking early is recommended.

FAQ

What is the best charter for a birthday in Chicago?
The Private Chicago Sailing Charter works well for classic birthday outings, while the Chicago Playpen Sailboat Charter is better for a more social summer lake day.
What is the best charter for a date night?
The Chicago Sunset Sailing Charter is usually the best fit for date nights, anniversaries, and special evenings.
Can we bring food and drinks?
Yes. BYOB and light food are welcome. Keep food simple and easy to serve onboard.
Are holiday weekends high demand?
Yes. Fourth of July, Memorial Day, Labor Day, and major summer weekends can book quickly.
Where do charters depart from?
Charters depart from Montrose Harbor in Chicago. Detailed boarding instructions are sent before your trip.