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$100-$300

Map View

Browse Lake Michigan Boat Rentals

4.9

(2,718 Reviews)

Page 3 of 8 • 189 listings

Events in Chicago · 12 guests

50 ft Double Decker Yacht | Sea Ray Bridge Express

5.0

$100person

Sailing in Chicago · 3 guests

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

4.8

$115-$120hour

Events in Chicago · 12 guests

Sea Ray Express 390 Luxury Charter in Chicago, Illinois

5.0

$300hour

Powerboats in Milwaukee · 12 guests

24 Foot Robalo on Lake Michigan, with bathroom!

5.0

$125hour

Events in Chicago · 12 guests

NEW!!! 35' Luxury Motor Yacht with 4’ swim platform in Chicago

5.0

$180-$270hour

Fishing in Racine · 6 guests

40ft Chris Craft for Fishing or Cruising on Lake Michigan

5.0

$145hour

Events in Chicago · 12 guests

SeaRay Sundancer 35' Motor Yacht Rental in Chicago, Illinois

5.0

$275hour

Events in Chicago · 8 guests

27 Sea Ray Sundancer Pre Season specials playpen party

5.0

$180hour

Events in Chicago · 12 guests

38ft Sea Ray Sundancer in Chicago, Burhnam Harbor (Up to 12 guests)

5.0

Superowner

Best of 2023

$250hour

Powerboats in Chicago · 12 guests

Chicago summer in style - 33' Monterey 302 for Charter on Lake Michigan!

4.8

Superowner

$250hour

Events in Chicago · 12 guests

40ft Boat w/ HUGE open seating area!

5.0

Superowner

Best of 2023

$210-$240hour

Sailing in Chicago · 6 guests

Charter this Beautiful Catalina 36 Sailboat w/Captain in Chicago, Illinois

5.0

$225hour

Powerboats in New Buffalo · 6 guests

2003 Cobalt 240 Bowrider Rental in St Joseph, Michigan

5.0

$225hour

Events in Chicago · 12 guests

53' Luxury Yacht w/Flybridge and Sundeck Rental in Chicago, Illinois

5.0

Superowner

$300-$400hour

Powerboats in New Buffalo · 6 guests

Cobalt 240 Bowrider for rent in New Buffalo (Captain Included!)

5.0

$225hour

Sailing in Chicago · 6 guests

Set Sail with 36' Sailing Boat in Downtown, Chicago

5.0

Superowner

$225hour

Powerboats in Michigan · 14 guests

22ft Bennington Tritoon for 14 pax on Glen Lake! Free delivery!

New

$113hour

Events in Chicago · 12 guests

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

5.0

Superowner

$250hour

Powerboats in Milwaukee · 6 guests

FourWinns Luxury Speed Boat available for Events, Date Nights and Family Outings

5.0

Superowner

$150hour

Events in Chicago · 8 guests

Luxury 33' Sea Ray - Come Charter & See Chicago!

5.0

$267hour

Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5

Superowner

$200hour

Events in Chicago · 12 guests

44ft of Luxury Yachting! Ask About Pre-Boating Season Discounts!!

5.0

$300hour

Powerboats in Milwaukee · 10 guests

Luxury Pontoon Boat Ride Along the Milwaukee River

5.0

$150hour

Powerboats in Chicago · 8 guests

Captained 27ft Bayliner Ciera Yacht in Chicago, Illinois

5.0

$250hour

Lake Michigan Reviews

SH
Susan
May, 2024
Set Sail with 36' Sailing Boat in Downtown, Chicago
A wonderful May sail. Great boat for 6 people to relax and enjoy the city skyline, while Ray tends to the sailing. Very competent sailor and friendly.
HW
Hector
May, 2024
Set Sail with 36' Sailing Boat in Downtown, Chicago
Very professional and yet easygoing captain. Boat was very nice - in excellent shape and well maintained. Highly recommend! We will be back again.
Jenna
May, 2024
50 ft Double Decker Yacht | Sea Ray Bridge Express
Great boat with good communication. Didn't love the captain but that was separate.
Tonu
August, 2022
Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
It was the perfect experience! Right from the beginning, I began steering, pulling the halyard and raising the main sail. I learned the basics easily and Ben is great to talk to because of his years of experience and pleasant demeanor. I very much enjoyed my time and even more so am happy to have learned so much so quickly. I highly recommend this for anyone trying to see what sailing is all about!
YH
Yousuf
August, 2022
Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
Our experience sailing with Ben was great. He is a pro and is clearly very passionate and knowledgeable about sailing. This passion is infectious, and we learned plenty from him. He also allowed us to take an active role in the process given our interest in sailing. Ben was also very personable, interesting, and pleasant to converse with, which is an important quality when sailing with someone! Would highly recommend!
Kimberly
September, 2021
Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
Benjamin communicated quickly and clearly and was super flexible as our plans changed. We rented the boat without a captain and he also provided a super helpful instruction sheet with every single thing we'd need to know... from harbor bathroom codes to the color of the jib sheet! So thorough and helpful, and it set us up for a perfect afternoon on the water. Thank you!