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Browse Illinois Boat Rentals.

Page 3 of 12277 listings

36' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )
Events in Chicago · 6 guests

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

5.0
$440/hour
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
**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
$300/hour
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
$275/hour
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
38-ft Party Pontoon for Up to 20 Guests in Chicago
Powerboats in Chicago · 20 guests

38-ft Party Pontoon for Up to 20 Guests in Chicago

5.0
Superowner
Best of 2025
$680/hour
Bayliner Ciera Motor Yacht Charter in Chicago, Illinois
Powerboats in Chicago · 10 guests

Bayliner Ciera Motor Yacht Charter in Chicago, Illinois

5.0
Superowner
$200/hour
14 Passenger Captained Party & Event Boat in Chicago, Illinois!
Powerboats in Chicago · 14 guests

14 Passenger Captained Party & Event Boat in Chicago, Illinois!

5.0
Superowner
$600/hour
27 Sea Ray Sundancer DM for October specials
Events in Chicago · 8 guests

27 Sea Ray Sundancer DM for October specials

5.0
$180/hour
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
Downtown Chicago, Party on the Lake!
Powerboats in Chicago · 10 guests

Downtown Chicago, Party on the Lake!

4.9
Best of 2025
$270/hour
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
46' Spacious Portofino Party Yacht in Chicago For Every Occasion
Events in Chicago · 12 guests

46' Spacious Portofino Party Yacht in Chicago For Every Occasion

4.5
$250/hour
2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!
Events in Chicago · 11 guests

2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!

5.0
$250/hour
Sea Ray Express 390 Luxury Charter in Chicago, Illinois
Events in Chicago · 12 guests

Sea Ray Express 390 Luxury Charter in Chicago, Illinois

5.0
$250/hour
Burnham Harbor, CAPTAIN/FUEL INCLUDED
Events in Chicago · 7 guests

Burnham Harbor, CAPTAIN/FUEL INCLUDED

5.0
$270+/hour
Wheelchair Accessible Pontoon Boat Chain-O-Lakes in Illinois Captain available
Powerboats in Antioch · 8 guests

Wheelchair Accessible Pontoon Boat Chain-O-Lakes in Illinois Captain available

5.0
$100+/hour
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
37' Luxury Sailing Yacht in Downtown Chicago
Sailing in Chicago · 10 guests

37' Luxury Sailing Yacht in Downtown Chicago

5.0
Superowner
$250+/hour
Maxum Yacht 44' in Chicago
Events in Chicago · 13 guests

Maxum Yacht 44' in Chicago

4.9
Superowner
Best of 2025
$268/hour
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
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
55' Sea Ray Luxury Yacht in Chicago
Events in Chicago · 12 guests

55' Sea Ray Luxury Yacht in Chicago

5.0
$325/hour

Illinois Reviews

  1. SK

    Sai

    27' Chris Craft with Water Toys plus Jet Ski Available

    Our experience with Captain Tim Jr was incredible! He is a fantastic captain, the boat was awesome, and he battled a storm to get us to the fountain, I proposed to my girlfriend, and he battled the storm right back to the dock. An experience we will never forget, best captain you could ask for!

  2. Christopher

    Christopher

    27' Chris Craft with Water Toys plus Jet Ski Available

    This was the perfect end to a long day for my family and me. Captain Tim was personable, attentive, and gracefully navigated a crowded waterfront for the 4th of July fireworks. The kids and I had a blast and enjoyed the relaxation. Would absolutely book again!

  3. bb

    bridget

    27' Chris Craft with Water Toys plus Jet Ski Available

    We booked a four hour trip for our family of four and absolutely loved it. We needed to reschedule our originally booked day due weather and Tim was very accommodating and flexible. Our experience on the water was perfect and exceeded our expectations for a family day out. I can’t wait to book again soon.

  4. DJ

    Dana

    27' Chris Craft with Water Toys plus Jet Ski Available

    Great experience! We had a wonderful and relaxing trip down the shore, taking amazing pictures. We really enjoyed just relaxing on the floatable and taking in the scenery. Tim was great too, communicating quickly and accommodating us when we parked in the wrong parking lot, causing us to be late. We would definitely rent with him again. It was an unforgettable day.

  5. Sabrae

    Sabrae

    27' Chris Craft with Water Toys plus Jet Ski Available

    Our boat ride with Captain Tim and first mate Diana was the perfect way to celebrate my husband‘s birthday. The boat accommodated the six of us perfectly allowing us to enjoy the ride together. We enjoyed the experience of going from the dock through the lake to the Chicago river and back. Captain Tim was able to expertly navigate the waters in spite of other boater’s behaving badly. We enjoyed Captain Tim allowing us to eat, drink and be merry for the whole ride. It was a beautiful night and he knew all the perfect spots for pictures. The next time I’m looking to rent a boat, Captain Tim will be my first choice!

  6. CS

    Chanel

    27' Chris Craft with Water Toys plus Jet Ski Available

    We had a great experience with Captain Tim. Leading up to the trip his communication was prompt. He was amenable to us adding an extra hour to our trip - it was no problem at all. During the trip - Captain Tim was great! He made sure the music was loud and that we always had drinks in our hands. It was a big plus to not have to bring water and ice (Captain Tim takes care of that for you). We loved relaxing on the pad behind the boat. Our day in the playpen was one of the best days of summer. I'll definitely contact Captain Tim for another boating adventure.