Chicago Sunset Sailing Charter
Watch the Chicago skyline glow from a private sailboat on Lake Michigan
From$927incl. taxes and fees
Duration
3 Hours
Ideal For
Up to 10 people
Includes
Private sail, captain, safety gear
Highlights
Sail Lake Michigan as the sun sets behind Chicago’s skyline. Your captain will select a route based on wind, weather, visibility, and lake conditions.
- Capture photos of Chicago from the water
- Experience a real sail rather than a motor-only cruise
- Relax with your group aboard a private charter
- Pack layers for cooler lake weather, plus towels and sunscreen
What's Included
- Private sailboat charter
- Licensed captain
- Life jackets and safety gear
- Onboard bathroom
Know before you go
- Bring your own drinks in cans only; glass is not allowed
- Expect the captain to determine whether lake and weather conditions are safe to sail
Cancellation Policy
30+ days before charter: deposit is non-refundable. 15–29 days before charter: 50% of the total charter price is non-refundable. 14 days or fewer before charter: 100% of the total charter price is non-refundable. Unsafe weather may be rescheduled for another available date.
FAQs
No separate fuel or docking fees apply.
Captain gratuity is appreciated but not required.
Meeting details
Montrose Harbor
Experience provided by Two Brothers Sailing Chicago
Experience provided by Two Brothers Sailing Chicago
Discover what we've curated for you