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$100-$300

Browse Illinois Boat Rentals.

Page 1 of 7152 listings

Enjoy the Fox River and Fox Chain!
Powerboats in Algonquin · 9 guests

Enjoy the Fox River and Fox Chain!

5.0
$100hour
Captain Memo's 28 ft. Sea Ray in Chicago
Events in Chicago · 8 guests

Captain Memo's 28 ft. Sea Ray in Chicago

5.0
Superowner
$250hour
27' Maxum 2400 Motor Yacht Rental in Chicago
Events in Chicago · 8 guests

27' Maxum 2400 Motor Yacht Rental in Chicago

3.5
$200hour
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing in Chicago · 6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

5.0
Superowner
Best of 2023
$220hour
32' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )
Events in Chicago · 6 guests

32' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )

4.9
Best of 2023
$300hour
Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!
Powerboats in Chicago · 6 guests

Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!

5.0
$175hour
Wellcraft Eclipse 233 Cuddy Cabin in Chicago, Illinois
Powerboats in Chicago · 8 guests

Wellcraft Eclipse 233 Cuddy Cabin in Chicago, Illinois

5.0
$225hour
Playpen bound on 25' Yamaha Jetboat!
Powerboats in Chicago · 10 guests

Playpen bound on 25' Yamaha Jetboat!

5.0
$225hour
Captained Charter on 38’ Carver Mariner with all the Amenities in Chicago, IL
Events in Chicago · 13 guests

Captained Charter on 38’ Carver Mariner with all the Amenities in Chicago, IL

4.9
Superowner
$275hour
Calling all Aquaholics! Luxury Cruising on Lake Michigan w/ 32' Chaparral Yacht
Powerboats in Chicago · 12 guests

Calling all Aquaholics! Luxury Cruising on Lake Michigan w/ 32' Chaparral Yacht

4.7
$300hour
Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Superowner
$200hour
36' Sundancer in Chicago
Events in Chicago · 13 guests

36' Sundancer in Chicago

5.0
$240-$250hour
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

5.0
Superowner
Best of 2023
$230hour
Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)
Events in Chicago · 12 guests

Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)

4.9
Superowner
Best of 2023
$250hour
Captained charter on 40' Sea Ray Sundancer with all amenities in Chicago
Events in Chicago · 13 guests

Captained charter on 40' Sea Ray Sundancer with all amenities in Chicago

5.0
Superowner
$275hour
Double Decker 50FT Sea Ray Flybridge Yacht!
Events in Chicago · 13 guests

Double Decker 50FT Sea Ray Flybridge Yacht!

5.0
Superowner
Best of 2023
$292hour
UP to  20 passengers Party Boat - Chicago Playpen or River trips
Powerboats in Chicago · 20 guests

UP to 20 passengers Party Boat - Chicago Playpen or River trips

5.0
Superowner
Best of 2023
$120person
46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 13 guests

46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois

5.0
$300hour
**Affordable Luxury Chicago Boat Rentals for 12 on Lake Michigan / Playpen**
Events in Chicago · 12 guests

**Affordable Luxury Chicago Boat Rentals for 12 on Lake Michigan / Playpen**

5.0
Superowner
Best of 2023
$250hour
33' Formula Motor Yacht - Great for Playpen!
Events in Chicago · 10 guests

33' Formula Motor Yacht - Great for Playpen!

5.0
$150hour
Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED
Events in Chicago · 7 guests

Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED

5.0
$300hour
*** $199 hr***Weekend Charter Rental - 33' Maxum!
Events in Chicago · 10 guests

*** $199 hr***Weekend Charter Rental - 33' Maxum!

4.8
$175hour
25ft Rinker - Captained Party - Chicago
Powerboats in Chicago · 6 guests

25ft Rinker - Captained Party - Chicago

4.9
Superowner
$180hour
37' Luxury Sailboat with Captain in Chicago, Illinois
Sailing in Chicago · 10 guests

37' Luxury Sailboat with Captain in Chicago, Illinois

5.0
Superowner
$299hour

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Illinois Reviews

  1. Okoye'

    Okoye'

    Captain Memo's 28 ft. Sea Ray in Chicago

    Memo is absolutely amazing! Please believe every great review left. He gives outstanding instructions as to where and how to find his boat. He had a cooler, floats, a large speaker- essentially everything we needed. My friends and I had a great time and will be back!

  2. Molly

    Molly

    Captain Memo's 28 ft. Sea Ray in Chicago

    Captain Memo made this experience unforgettable, just like the name of his boat! He made sure we knew exactly where to meet him at the time of departure, supplied coolers and ice for us and had all the lake floats blown up and ready for us to relax in the lake. He is trustworthy and all around a great guy. Thank you Captain Memo for an unforgettable time!!

  3. BS

    Berin

    Captain Memo's 28 ft. Sea Ray in Chicago

    If you click out of Memo's page without booking, you're making a mistake! Memo was BEYOND anything my family could have imagined. Our group of 5 had one of the best times on his boat and he is the DEFINITION of hospitality. Memo is a GEM!!!!!!! BOOK WITH HIM!!!!!!

  4. GM

    Gwyn

    Captain Memo's 28 ft. Sea Ray in Chicago

    Couldn’t ask for a better cap to a first weekend experiencing Chicago. Captain Memo went out of his way to make the experience special, from making sure we always had a full drink in hand, to creating some Titanic-esque front of boat moments, to letting us take a turn at the helm. He even voluntarily let our time run long because we were all vibing to Frank Sinatra on the way back in to the docks. You will have a great time because he’s just a generally kind soul. Oh captain my captain!

  5. LB

    Laura

    Captain Memo's 28 ft. Sea Ray in Chicago

    We had an absolute blast with Captain Memo! He is the most accommodating and kind person and went above and beyond many times over to make our experience one of the best times we could ever imagine. We can’t recommend him highly enough! Thank you Captain Memo!

  6. HG

    Harsha

    Captain Memo's 28 ft. Sea Ray in Chicago

    This was our first time on a boat all for ourselves. I planned to celebrate my fiancé s birthday on the boat. I wanted to cut the cake on the boat at the Playpen . Captain Memo was so accommodating and very easy to work with. He made the trip a memorable and fun experience. Overall definitely recommended. We will return back soon