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Lake Michigan, US Boat Rentals & Yacht Charters

4.9

(6,577 Reviews)

Page 2 of 15 • 356 listings

Limited Availability

Powerboats in Chicago · 5 guests

Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob

5.0

Superowner

$225/hour

Limited Availability

Events in Chicago · 12 guests

Top of the line Sea Ray Sundancer 340 Motor Yacht - Accommodate 12 Guests

3.9

$250/hour

Powerboats in Milwaukee · 12 guests

12 Person, 24 Foot Robalo on Lake Michigan, with bathroom!

5.0

$115+/hour

Sailing in Chicago · 6 guests

Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat

5.0

$225/hour

Limited Availability

Events in Chicago · 6 guests

62ft Azimut Italian Yacht Charter Chicago for Up to 6 Guests

5.0

Superowner

Best of 2026

$500/hour

Instant Book

Powerboats in Chicago · 16 guests

16 Passenger Captained Party & Event 32ft Pontoon Boat in Chicago, Illinois!

5.0

Superowner

Best of 2026

$650/hour

Limited Availability

Events in Chicago · 13 guests

45' Formula 400 Super Sport Luxury Yacht Charter at Navy Pier Marina

5.0

$300/hour

Limited Availability

Events in Chicago · 12 guests

Enjoy Chicago aboard 45' Sea Ray Express Cruiser Yacht - Perfect for Parties!

4.9

Superowner

Best of 2026

$400/hour

Instant Book

High Demand

Events in Chicago · 13 guests

Chicago 40ft Formula Performance Cruiser for Up to 13 Guests

5.0

$349/hour

Powerboats in Chicago · 5 guests

27ft Sea Ray Deck Boat for 5 Guests, Captain Included

5.0

$235/hour

Limited Availability

Events in Chicago · 13 guests

Book "After Hours" today! Sea Ray Sundancer 40ft Motor Yacht In Chicago

5.0

Superowner

Best of 2026

$225+/hour

Events in Chicago · 12 guests

Catch a summer vibe on the water aboard 39' Sea Ray motor yacht

5.0

$225/hour

Limited Availability

Events in Chicago · 6 guests

New 48ft Sport Coupe Yacht in Chicago River & Lake Charter

4.9

$300/hour

Limited Availability

Powerboats in Chicago · 10 guests

Cruisers Y3375 Express Yacht Downtown Chicago Experience

5.0

Superowner

$250/hour

Tours in Chicago · 6 guests

Sailing Lessons with Chicago's #1 Rated Sailing School

5.0

$175+/hour

Powerboats in Michigan · 14 guests

Explore Glen Lake with Spacious Bennington Pontoon!

5.0

$100/hour

Events in Chicago · 13 guests

50ft Double Deck Yacht "Liquid Asset 3" in Chicago!

5.0

Superowner

Best of 2026

$300/hour

Powerboats in Michigan · 12 guests

MasterCraft X24 Wakeboard/Wakesurf /Foil/Tube or Hangout Up to 12 Guests

5.0

$295/hour

Powerboats in Chicago · 8 guests

Captained 27ft Bayliner Ciera Yacht in Chicago, Illinois

4.6

$275/hour

Limited Availability

Events in Chicago · 12 guests

Explore the Famous Chicago Playpen! - 46ft Sea Ray Motor Yacht!

5.0

Superowner

Best of 2026

$220/hour

Instant Book

Events in Chicago · 7 guests

Captained 51' Sea Ray Sundancer Luxury Yacht in Chicago - 7 Guests

5.0

Superowner

$500+/hour

Sailing in Chicago · 6 guests

Set Sail with 36' Sailing Boat in Downtown, Chicago for 6 Guests

5.0

$225/hour

Travel in Saugatuck · 25 guests

Book a Private Charter to cruise on Lake Kalamazoo with a U.S.C.G Master Captain

5.0

$350/hour

High Demand

Sailing in Muskegon · 6 guests

41' Morgan Classic Sloop in Muskegon, Michigan!!!

5.0

$100/hour

Top Destinations Nearby

Lake Michigan Reviews

Beverly

27ft Sea Ray Deck Boat for 5 Guests, Captain Included
We all had an amazing time on Bobby’s boat! The boat was in pristine condition and was equipped with a cooler with ice and water bottles which was much appreciated. My girlfriend and I took her daughter and friend for their first time on Lake Michigan and Bobby was very accommodating. He made sure everyone felt safe and had fun! Even took out his lily pad for the girls to enjoy! Such a great day!
Cheri Ann

Captained 51' Sea Ray Sundancer Luxury Yacht in Chicago - 7 Guests
Chris and his lovely wife hosted my family of 6 on their vessel for the 4th of July. He stayed in constant communication before the trip and also discussed the weather. He offered ideas for the perfect 5 hours on the Lake, and was not wrong. The couple was the perfect host. Their boat was beautiful. They gave us the best day!
MB
Moriah

Cruisers Y3375 Express Yacht Downtown Chicago Experience
This was a great activity for our bachelorette party! Ramsey's communication was excellent throughout planning, and the boat itself was both aesthetic for pictures and fun to hangout on. Highly recommend!
Michael

50ft Double Deck Yacht "Liquid Asset 3" in Chicago!
Fantastic! I have used Chris’ fleet multiple times now. They’re pros. They make everything fun and approachable. The vessels are great and you get what’s advertised.
Sarju

Cruisers Y3375 Express Yacht Downtown Chicago Experience
Ramsye was very responsive and accomodating on short notice and provided us with a captain and crew that was very kind and ensured we had a good time
PS
Paige

New 48ft Sport Coupe Yacht in Chicago River & Lake Charter
I thoroughly enjoyed my experience! The captain and first mate were very helpful and respectful. Everything went smoothly with the charter. I would recommend them!