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Browse Lake Michigan Boat Rentals

Page 1 of 367 listings

Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Powerboats in Chicago · 12 guests

Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

5.0
Best of 2025
$165/hour
Instant Book
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
Events in Chicago · 12 guests

Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht

5.0
Best of 2025
$175/hour
Instant Book
2020 Beneteau GT 42' "James Bond" Yacht — Book Now for Summer 2025
Events in Chicago · 12 guests

2020 Beneteau GT 42' "James Bond" Yacht — Book Now for Summer 2025

4.7
$400/hour
Instant Book
2hr Day Sail from the port of South Haven Mi. on a Catalina 36
Sailing in South Haven · 6 guests

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

5.0
$175/hour
Instant Book
Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat
Events in Chicago · 12 guests

Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat

5.0
$250/hour
Instant Book
Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Sailing in Milwaukee · 6 guests

Captained Charter 30' Sailboat in Milwaukee, Wisconsin

5.0
$150/hour
Instant Book
27' Chris Craft with Water Toys plus Jet Ski Available
Powerboats in Chicago · 6 guests

27' Chris Craft with Water Toys plus Jet Ski Available

4.9
Superowner
$235/hour
Instant Book
50' Multi-level Luxury Yacht with Party up to 12
Events in Chicago · 12 guests

50' Multi-level Luxury Yacht with Party up to 12

5.0
Superowner
Best of 2025
$350+/hour
Instant Book
Enjoy Chicago! Beautiful 31' Sea Ray Sundancer - Perfect for any Occasion
Events in Chicago · 10 guests

Enjoy Chicago! Beautiful 31' Sea Ray Sundancer - Perfect for any Occasion

4.9
Best of 2025
$275+/hour
Instant Book
25ft Rinker - Captained included in price- Chicago
Powerboats in Chicago · 7 guests

25ft Rinker - Captained included in price- Chicago

4.9
Superowner
$199/hour
Instant Book
Ultimate 52 " Yacht at Diversey Harbor –Perfect for PlayPen!
Events in Chicago · 12 guests

Ultimate 52 " Yacht at Diversey Harbor –Perfect for PlayPen!

5.0
$300/hour
Instant Book
Enjoy Chicago! 46' Beautiful Sea Ray Yacht - Perfect for Parties
Events in Chicago · 12 guests

Enjoy Chicago! 46' Beautiful Sea Ray Yacht - Perfect for Parties

5.0
Best of 2025
$400/hour
Instant Book
Experience Lake Michigan like never before on Beautiful 35ft Maxum
Events in Chicago · 10 guests

Experience Lake Michigan like never before on Beautiful 35ft Maxum

5.0
$225/hour
Instant Book
Charter a 40' Luxury Gran Tursimo Yacht for 11 guests w/ Captain in Chicago
Events in Chicago · 11 guests

Charter a 40' Luxury Gran Tursimo Yacht for 11 guests w/ Captain in Chicago

4.8
$350/hour
Instant Book
62' $2M Italian Luxury Yacht with Party up to 12
Events in Chicago · 12 guests

62' $2M Italian Luxury Yacht with Party up to 12

5.0
Superowner
Best of 2025
$800/hour
Instant Book
42' Luxury Mediterranean Yacht w/ Captain in Chicago - Two Yachts available
Events in Chicago · 12 guests

42' Luxury Mediterranean Yacht w/ Captain in Chicago - Two Yachts available

5.0
$350/hour
Instant Book
37' Beautiful Sea Ray Venture - Explore Chicago's Famous Playpen
Events in Chicago · 12 guests

37' Beautiful Sea Ray Venture - Explore Chicago's Famous Playpen

New
Best of 2025
$400/hour
Instant Book
Enjoy Chicago in this 45' Sea Ray Express Cruiser Yacht - Perfect for Parties!
Events in Chicago · 12 guests

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

4.9
Best of 2025
$400/hour
Instant Book
33ft Day Boat in Chicago
Events in Chicago · 10 guests

33ft Day Boat in Chicago

4.9
$275/hour
Instant Book
Stunning Multi-Level 47’ Carver Yacht in Chicago for up to 13 Guests
Events in Chicago · 12 guests

Stunning Multi-Level 47’ Carver Yacht in Chicago for up to 13 Guests

4.8
$350/hour
Instant Book
37' Spacious Party Yacht For Every Occasion
Events in Chicago · 12 guests

37' Spacious Party Yacht For Every Occasion

5.0
$225/hour
Instant Book
41' Stunning Sea Ray Yacht - Stunning throughout
Events in Chicago · 13 guests

41' Stunning Sea Ray Yacht - Stunning throughout

5.0
$350/hour
Instant Book
NEW!!! SPACIOUS 40ft Cruisers Yacht, Power…in the Lake, Chicago
Events in Chicago · 12 guests

NEW!!! SPACIOUS 40ft Cruisers Yacht, Power…in the Lake, Chicago

5.0
Superowner
$400/hour
Instant Book
1962 Chris Craft Yacht Charter on the Chicago River!
Events in Chicago · 6 guests

1962 Chris Craft Yacht Charter on the Chicago River!

5.0
$300+/hour
Instant Book

Lake Michigan Reviews

  1. Mardysa

    Mardysa

    Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

    I had an amazing time! I booked on rather short notice and Kevin came through for me especially with helping to find a captain for such a busy day. The entire process was smooth and Captain Lisa was great! I’d definitely book with him again in the future.

  2. karina

    karina

    Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

    Kevin was super nice and accommodating. Any question I asked he answered. Was able to provide me a captain on short notice. The boat itself was super clean! Even the bathroom. And it was a full bathroom. Very happy with purchase and experience. Thank you kevin!

  3. Tay

    Tay

    Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht

    I swear, if I could give 10 stars, I would! :-)My cousins and I had a remarkable experience on our family outing! Kevin is super professional and ensured our boat day went smoothly, we had some rough weather conditions on our initial date, but thankfully Kevin was able to switch us out for the next day—Very accommodating of him and we were truly grateful for that. Don’t hesitate to book his boat. Oh and I can’t forget the best captain ever, Jimmy! 😎 He’s amazing, super fun/chill and knows the all best spots to take great pictures. 11 out of 10 recommend! 👌🏾

  4. ZJ

    ZJ

    Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht

    I booked with Kevin for my boyfriends birthday surprise and it was EVERYTHINGGGG !!! my boyfriend was soooo happy and our friends and us had SO MUCH FUN !! 1000000/10 would recommend !! This was the best first time experience EVER !! thank you thank you thank you for helping me make my boyfriends birthday so special and a core memory we’ll have forever 💙 !!

  5. MR

    Merilyn

    2020 Beneteau GT 42' "James Bond" Yacht — Book Now for Summer 2025

    Everything went smooth and our captain John was incredible and so sweet! Captain John always looked out for our safety especially since our experience was during the nighttime. Was helpful that he was able to provide some water and other beverages. We had an amazing experience with Nilufar’s boat!!

  6. AT

    Ayush

    2020 Beneteau GT 42' "James Bond" Yacht — Book Now for Summer 2025

    Everything from the booking to getting on-board was a smooth sail (pun intended). I really appreciate the quick responses to help us navigate through the process. Boat was very nice and well kept. Will definitely consider again for next time and would also recommend friends.