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Boat Rentals Near You

4.9
(13,489 Reviews)

Page 2 of 10240 listings

61’ Gorgeous Sunseeker Predator Weekday Special Rates
Events in Chicago · 13 guests

61’ Gorgeous Sunseeker Predator Weekday Special Rates

4.8
Superowner
$280/hour
Instant Book
Luxury 40 ft. Sea Ray Sundancer Motor Yacht in Chicago, Illinois
Events in Chicago · 12 guests

Luxury 40 ft. Sea Ray Sundancer Motor Yacht in Chicago, Illinois

5.0
$300/hour
Instant Book
53' Luxury Yacht w/Flybridge and Sundeck Rental in Chicago, Illinois
Events in Chicago · 12 guests

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

5.0
Superowner
$375/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

4.7
$250/hour
Instant Book
Stunning 45’ Sea Ray Yacht
Events in Chicago · 12 guests

Stunning 45’ Sea Ray Yacht

5.0
Superowner
$350/hour
Instant Book
Spacious 37' Rinker Express - Perfect for Lake Michigan Adventures
Events in Chicago · 12 guests

Spacious 37' Rinker Express - Perfect for Lake Michigan Adventures

New
Snoozed - Active 02 Nov 2025
Luxury Unleashed – 40ft Sea Ray Dream Cruiser
Events in Chicago · 12 guests

Luxury Unleashed – 40ft Sea Ray Dream Cruiser

New
$450/hour
Instant Book
450 Sea Ray Sundancer. Yes we upgraded but we kept the low price. Check us out!
Events in Chicago · 10 guests

450 Sea Ray Sundancer. Yes we upgraded but we kept the low price. Check us out!

5.0
$350/hour
Instant Book
Luxury 35' Silverton 330 Sport Bridge Yacht Rental in Chicago!
Events in Chicago · 10 guests

Luxury 35' Silverton 330 Sport Bridge Yacht Rental in Chicago!

5.0
$350/hour
Instant Book
A Unique Experience With Our Sea Ray 330 Sundancer
Powerboats in Chicago · 7 guests

A Unique Experience With Our Sea Ray 330 Sundancer

New
$395/hour
Instant Book
24’ Robalo CC Lake Michigan charters. Downtown Chicago to the Indiana beaches
Powerboats in Chicago · 5 guests

24’ Robalo CC Lake Michigan charters. Downtown Chicago to the Indiana beaches

5.0
Snoozed - Active 18 Aug 2025
36ft Carver Mariner Motor Yacht in Chicago
Events in Chicago · 12 guests

36ft Carver Mariner Motor Yacht in Chicago

4.9
Snoozed - Active 18 Aug 2025
39' Sea Ray for Rent in Chicago, Illinois!
Events in Chicago · 12 guests

39' Sea Ray for Rent in Chicago, Illinois!

5.0
$350+/hour
Instant Book
Sea Ray 370 Sundancer Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 12 guests

Sea Ray 370 Sundancer Motor Yacht Rental in Chicago, Illinois

5.0
Snoozed - Active 03 Aug 2025
46' Azimut Quartano Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 13 guests

46' Azimut Quartano Motor Yacht Rental in Chicago, Illinois

5.0
$650/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
Li'l Red, Crownline CR250 Cabin Cruiser.
Powerboats in Chicago · 10 guests

Li'l Red, Crownline CR250 Cabin Cruiser.

5.0
Best of 2025
$325/hour
Instant Book
Lakeside Paradise Escape with Premier 310 Escalante Double Decker Tritoon
Powerboats in Dandridge · 12 guests

Lakeside Paradise Escape with Premier 310 Escalante Double Decker Tritoon

New
$333/hour
Instant Book
Sail & Swim from a Luxury Sailing Yacht
Sailing in Chicago · 7 guests

Sail & Swim from a Luxury Sailing Yacht

5.0
Superowner
$150/hour
Instant Book
26 ft. Chaparral SSX257 Luxury Vessel
Powerboats in Chicago · 10 guests

26 ft. Chaparral SSX257 Luxury Vessel

5.0
$200/hour
Instant Book
Luxury 29ft Crownline Bowrider 285 SS
Powerboats in Chicago · 10 guests

Luxury 29ft Crownline Bowrider 285 SS

5.0
$250/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
Luxury 28 ft Chaparral 277 SSX Vessel
Powerboats in Chicago · 10 guests

Luxury 28 ft Chaparral 277 SSX Vessel

New
$250/hour
Instant Book
 Chicago Water Music on the Chicago River Scenic River cruises with live music
Powerboats in Chicago · 19 guests

Chicago Water Music on the Chicago River Scenic River cruises with live music

New
$800+/hour
Instant Book

Local Reviews

  1. ME

    Makaeda

    Luxury 35' Silverton 330 Sport Bridge Yacht Rental in Chicago!

    This was our groups first experience in Lake Michigan. The waves were definitely something we’ve never experienced but the hospitality from Mike, Tony and the crew was amazing they were very warm and welcoming and we had a great time during our trip. We would definitely book with them again and recommend.

  2. OT

    Olivia

    Stunning 45’ Sea Ray Yacht

    Fantastic Experience with Peter and Team! Peter was incredible—he even met us in the parking lot with a wagon to help transport our drinks and food. He was extremely friendly and communicative from start to finish. My coworkers and I had an amazing time cruising around the lake. The only minor downside was needing to bring our own ice, but everything else was absolutely 10/10. We’ll definitely be booking with Peter and his team again!

  3. cf

    carolynn

    Sail & Swim from a Luxury Sailing Yacht

    This is an iconic trip in Chicago. I have always been on the river walk or on a kayak looking at people boats and thought "Those lucky kids." So this time I rented a sailboat to go out on the lake- even luckier! The operators are very organized and helpful. Everything was as expected from the site. Communication throughout was excellent. Thanks for lovely and memorable sail. I'm coming back to jump in the lake when the water temperature is a bit warmer :)

  4. RJ

    Rachel

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

    Captain Jim and his team went above and beyond to make our charter an unforgettable experience. From the moment we departed to the smooth arrival back at the dock, everything was handled with professionalism, confidence, and a warm, friendly attitude. The boat was immaculate, the ride was smooth, and Captain Jim clearly knew the waters like the back of their hand. They made us feel safe, relaxed, and completely taken care of the entire time. Whether it was pointing out interesting sights, adjusting course for the best views, or making sure we had everything we needed on board, their attention to detail was exceptional. You can tell they truly love what they do—and it shows in the way they connect with guests and manage every aspect of the trip seamlessly. I highly recommend Captain Jim and his team, to anyone looking for a top-tier charter experience. Thank you again for an incredible day on the water!

  5. MA

    Mahab

    46' Spacious Portofino Party Yacht in Chicago For Every Occasion

    Had the best time out on the water with Captain Kyle! He was super professional, friendly, and made sure we felt comfortable and had fun the entire trip. The boat was clean, spacious, and had everything we needed. Kyle knew all the best spots and kept the vibe fun and relaxed. You can tell he really knows what he’s doing and loves what he does. Highly recommend booking with him — can’t wait to go out again!

  6. JF

    James

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

    Amazing boat! Clean, large, and stored at a great marina to spend time at before or after. Very professional and friendly owner. Captain Dean was our captain and made the experience really fun and safe for all. Highly recommend!