Memorial Day Weekend Boat Charter Chicago
Start summer on Lake Michigan with a private Memorial Day weekend boat charter from Montrose Harbor.
Private charters from Montrose Harbor. BYOB-friendly. Restroom onboard.
Start the Chicago Summer on the Water
Memorial Day weekend marks the unofficial start of summer in Chicago, and a private Lake Michigan charter is one of the best ways to make the weekend feel special.
This charter is ideal for groups who want skyline views, lake time, and a relaxed holiday weekend experience without booking another crowded patio, rooftop, or public cruise.
Why it's a fit
Marks the start of summer without a spreadsheet of stops.
Bring friends, family, or guests who flew in for the long weekend.
Holiday patios fill fast; on the water you’ve got air and elbow room.
Lake and skyline together—that postcard view everyone expects from Chicago.
You’ll know where to meet at Montrose Harbor before you leave the house.
Recommended Charter Options
What to Expect
Meet at Montrose Harbor
Arrive at the harbor and meet your captain near the boarding location.
Board the boat and get settled
Step aboard, get settled, and store your drinks, snacks, and belongings.
Review a short safety briefing
Your captain will review basic safety information before leaving the dock.
Cruise Lake Michigan
Enjoy skyline views, light conversation, photos, and relaxed time on the water.
Enjoy skyline views and holiday weekend lake time
Relax into skyline views and holiday-weekend lake time.
Return to the same dock
Your charter ends back at the original boarding location.
Planning Tips
Book early for holiday weekend availability.
Bring layers because early-season lake temperatures can feel cooler.
Bring drinks, snacks, sunglasses, and sunscreen.
Expect more lake activity than a typical weekday.
Route depends on weather, lake conditions, and captain discretion.
What's Included
Private use of the sailboat
Experienced captain / captain arrangement
Safety briefing before departure
Required safety gear onboard
Restroom onboard
Cooler/storage space
Boarding instructions before your trip
Weather monitoring before departure
Good to Know
Memorial Day weekend weather in Chicago can vary. Lake conditions, temperature, and route will be reviewed before departure, and safety always comes first.
FAQ
Is Memorial Day weekend a good time for a boat charter?
Is the boat private?
Can we bring drinks and snacks?
Where do we board?
What should we wear?
Start Summer on Lake Michigan
Book a private Memorial Day weekend boat charter and enjoy Chicago from the water.
