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Chicago, Illinois Boat Rentals & Yacht Charters

4.9

(6,395 Reviews)

Page 9 of 12 • 285 listings

Events in Chicago · 24 guests

50' Corinthian Big Party Boat for up to 24 people at Navy Pier Marina

5.0

$1,136/hour

Events in Chicago · 6 guests

Beautiful 37’ Sea Ray Sundancer Motor Yacht Out of Navy Pier Marina

New

$350+/hour

Events in Chicago · 6 guests

32ft SeaRay Sundancer Motor Yacht for Charter in Chicago for 6 Guests

5.0

$300/hour

Sailing in Chicago · 10 guests

Private Cruise on 40’ Luxury Sailing Yacht - Beneteau Oceanis 393 “Vagabond”

5.0

$275/hour

Events in Chicago · 13 guests

No Tie Ups - 40ft Sea Ray Yacht lots of room for 13 at DuSable Harbor

5.0

$250/hour

Events in Chicago · 10 guests

Set Sail in Downtown Chicago with Beautiful 35ft Cruiser Motor Yacht

5.0

$275/hour

Events in Chicago · 10 guests

37ft Cruiser Express Motor Yacht Charter Chicago Plus Jet Ski Included

4.3

$350/hour

Events in Chicago · 10 guests

Awesome Deal! | Cruise Chicago in Style on a 40' Beneteau Grand Turismo Yacht!

5.0

$300+/hour

Events in Chicago · 120 guests

Tiki-Chic Yacht, 40-120 Passengers, One deck option. Beverage package included!

5.0

$1,500/hour

Events in Chicago · 12 guests

Private 44ft Cruiser 4450 Express Yacht Experience on Lake Michigan – Chicago

5.0

$325/hour

Events in Chicago · 45 guests

68' Luxurious Chris Craft Roamer Yacht Private Yacht Charters in Chicago

5.0

$1,750/hour

Events in Chicago · 12 guests

40' Regal Commandore Luxury Cruiser in Chicago

5.0

$300/hour

Events in Chicago · 13 guests

Chicago: 52' Cruisers Express Luxury Yacht for Private Lake Michigan Cruises

5.0

$750/hour

Events in Chicago · 13 guests

New Boat in Chicago! 55ft Sea Ray Sundancer, Sleek & Spacious

New

Superowner

Best of 2026

$450/hour

Powerboats in Chicago · 6 guests

Tiki Themed 24' Key West Boat with Captain & Beverage Package | Chicago

5.0

$200/hour

Events in Chicago · 12 guests

34' Chris-Craft Yacht for Lakefront Fun! Music Lights and a Great time!!!

New

$300/hour

Events in Chicago · 12 guests

Diversey Harbor - 42' Sea Ray Sundancer Luxury Motor Yacht - Fuel Included

4.0

$150/hour

Limited Availability

Events in Chicago · 12 guests

Catch a summer vibe on the water aboard 39' Sea Ray motor yacht

5.0

$225/hour

Events in Chicago · 11 guests

35’ Sea Ray Yacht, Playpen, River Cruises up to 13 people Captain included!

5.0

$300/hour

Powerboats in Chicago · 8 guests

Fun 27' Chaparral Sunesta Boat Rental in Chicago: Skyline Views on Lake Michigan

5.0

$284/hour

Events in Chicago · 12 guests

Sea Ray 370 Sundancer Motor Yacht Rental in Chicago - USCG Captain Required

5.0

$325/hour

Events in Chicago · 12 guests

36’ Monterey for 12 Guests in Chicago | Playpen Party, BYOB & Captain included

1.5

$300/hour

Events in Chicago · 90 guests

Skipperliner Tiki Party Yacht for 50–90 Guests All Inclusive in Chicago

5.0

$1,500/hour

Water Sports in Chicago · 3 guests

SeaDoo GTR 230 or RXT-X 300 Jet Ski Adventures on Lake Michigan

5.0

$100+/hour

Top Destinations Nearby

Chicago Reviews

MO
Maddy

No Tie Ups - 40ft Sea Ray Yacht lots of room for 13 at DuSable Harbor
Great rental! Martin was very communicative, loved that the pricing was all inclusive of the tip. Boat was large, complimentary floaties and lilypad included. Highly recommend
Amelia

Diversey Harbor - 42' Sea Ray Sundancer Luxury Motor Yacht - Fuel Included
Our group had the best time! Paul’s boat was perfect for our group size and he was very responsive leading up to the boat. Thanks Paul!
Jet

50' Corinthian Big Party Boat for up to 24 people at Navy Pier Marina
We rented this boat for my bachelorette and it was amazing! The crew was awesome and the boat was perfect for what we needed. Highly recommend and would rent again!
Cheri Ann

32ft SeaRay Sundancer Motor Yacht for Charter in Chicago for 6 Guests
We had an amazing day with Nick and his brother Ryan on their boat!! They took care of everything we needed, made sure we had an amazing day and were very accommodating! The boat was beautiful, and very clean! We are already booking our next day out!
LD
Lisa

32ft SeaRay Sundancer Motor Yacht for Charter in Chicago for 6 Guests
Second time out with Nick. Each experience has been above and beyond. Looking forward to our next time on his beautiful boat. He’s alway very accommodating and gracious. Highly, highly recommend. A little piece of heaven right here in our beautiful city.
PD
Paul

32ft SeaRay Sundancer Motor Yacht for Charter in Chicago for 6 Guests
This was an amazing experience! Captain Nick was accommodating and both he and Ryan made us feel welcome from the moment we boarded. The boat was very clean and well taken care of. They provided us our privacy and yet were attentive if we needed anything. It was a beautiful day enjoying the city view, water and sun. It was a special touch when they presented us with a bottle of champagne and anniversary card....highly recommend!