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Michigan, US Boat Rentals & Yacht Charters

4.9

(7,233 Reviews)

Page 4 of 17 • 403 listings

Powerboats in Chicago · 12 guests

Set Sail on a Spacious 42' Silverton Express Cruiser Yacht

5.0

$275/hour

High Demand

Events in Chicago · 13 guests

Meridian 38 Luxury Yacht Multi-Level Private Charter with Water Toys in Chicago

4.9

Superowner

$250/hour

Instant Book

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 · 12 guests

Luxury Boating Experience in Chicago aboard Sea Ray 550 Sedan Bridge Yacht

5.0

Superowner

Best of 2026

$450/hour

Instant Book

Events in Chicago · 6 guests

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

5.0

Superowner

Best of 2026

$500/hour

Events in Chicago · 12 guests

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

3.9

$250/hour

High Demand

Events in Chicago · 12 guests

Clean 40' Sea Ray Motor Yacht With Plenty of Room and Incredible Sound System!

5.0

$350/hour

Events in Chicago · 12 guests

Ready to Use Doral Alegria 50' Yacht in Chicago, Illinois

5.0

$225/hour

Events in Chicago · 12 guests

38' Four Winns 378 Vista Motor Yacht in Chicago, Illinois

4.8

$408/hour

Events in Chicago · 12 guests

Professionally Maintained 50' Sea Ray Sundancer for 12 Passengers in Chicago

4.9

$350/hour

Events in Chicago · 13 guests

Chicago 40ft Formula Performance Cruiser for Up to 13 Guests

5.0

$349/hour

Events in Chicago · 12 guests

Soak Up the Sun Onboard a 42' Sea Ray Express Cruiser in Chicago

5.0

$275/hour

Powerboats in Chicago · 5 guests

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

5.0

$235/hour

Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5

$200+/hour

High Demand

Powerboats in Chicago · 13 guests

Double Decker 50ft Sea Ray Flybridge Yacht in Chicago - 13 Guests

5.0

Superowner

Best of 2026

$300+/hour

High Demand

Events in Chicago · 13 guests

52' Sea Ray Motor Yacht - Largest Boat at Diversey Harbor – Perfect for PlayPen!

5.0

$225+/hour

Powerboats in Madison · 10 guests

Harris Boats 210 Cruiser SL Pontoon Rental in Madison, Wisconsin

5.0

$80+/hour

Powerboats in Pewaukee · 8 guests

21ft SeaRay SunDeck for Pewaukee Lake. Other lakes by request.

5.0

$165+/hour

Sailing in South Haven · 6 guests

2hr Day Sail from the port of South Haven Mi. on a Catalina 36

5.0

$175/hour

High Demand

Events in Chicago · 30 guests

Stunning 105ft Denison Party Yacht in Chicago

4.7

$1,450+/hour

Events in Chicago · 12 guests

SeaRay 330 Motor Yacht Charter in Chicago, Illinois for 12 Guests

5.0

$200/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 · 12 guests

39' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois

5.0

Superowner

Best of 2026

$342+/hour

High Demand

Powerboats in Chicago · 9 guests

Gorgeous 26ft Chaparral 257SSX Bowrider in Chicago

5.0

$150/hour

Top Destinations Nearby

Michigan Reviews

VB
Victoria

39' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
Everytime I've driven on Lakshore Drive and seen all the people out in their boats having fun, I've thought about how nice it would be to rent one. I finally did for my birthday and it was a perfect afternoon! Boat very clean, well-managed, and friendly and helpful captain. Will rent again from Cap't James.
Alexandra

Gorgeous 26ft Chaparral 257SSX Bowrider in Chicago
Our group had a great time with Mark’s boat; our captain Eduard was fantastic too! Easy to find the meeting point, plenty of time in the water, and just a great day! The lily pad was a nice addition as well. Would definitely recommend for a smaller group looking to be on the lake.
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!
JC
Jayme

Clean 40' Sea Ray Motor Yacht With Plenty of Room and Incredible Sound System!
George was a great captain. Really friendly and accommodating. We had such a fun time at the playpen. Organizing the logistics were seamless as well. Highly recommend.
Ryan

52' Sea Ray Motor Yacht - Largest Boat at Diversey Harbor – Perfect for PlayPen!
Jason’s boat was exactly what we needed and he was friendly and very responsive. Would definitely book again!
RT
Rya

39' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
I’d highly recommend Captain James’ boating charter! My friends and I went to the playpen and had the best time. The boat had plenty of room for our group and was very clean. We used Captain Daniel Chavez for our charter. He was awesome! Overall this was a great experience!!