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Chicago, Illinois Boat Rentals & Yacht Charters

4.9

(6,382 Reviews)

Page 9 of 13 • 290 listings

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

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

5.0

$300+/hour

Events in Chicago · 12 guests

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

5.0

$325/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 · 120 guests

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

5.0

$1,500/hour

Limited Availability

Sailing in Chicago · 6 guests

Set Sail on a classic 36' S2 in Chicago for up to 6 Guests

5.0

$200/hour

Events in Chicago · 13 guests

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

5.0

$750/hour

Events in Chicago · 10 guests

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

4.3

$350/hour

Events in Chicago · 12 guests

40' Regal Commandore Luxury Cruiser in Chicago

5.0

$300/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

Events in Chicago · 45 guests

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

5.0

$1,750/hour

Limited Availability

Events in Chicago · 13 guests

Chicago's Newest 40ft Sea Ray Sundancer Luxury Motor Yacht

5.0

$250/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 · 8 guests

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

5.0

$284/hour

Events in Chicago · 11 guests

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

5.0

$300/hour

Events in Chicago · 12 guests

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

1.5

$400/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 · 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

Events in Chicago · 13 guests

2018 Luxury 52ft Azimut Fly 50 Motor Yacht Rental in Chicago, IL for 13 Guests

5.0

$1,000/hour

Events in Chicago · 12 guests

2020 Sea Ray SLX 400 Motor Yacht in Chicago, Illinois for 12 Guests

5.0

$1,000/hour

Events in Chicago · 12 guests

40' Carver Motor Yacht with space all around available in Chicago

5.0

$375/hour

Top Destinations Nearby

Chicago Reviews

Vince

Set Sail on a classic 36' S2 in Chicago for up to 6 Guests
Highly recommend, Planned a surprised engagement, and Ted and Christy were awesome. Super accommodating, friendly, and went out of their way to make the experience very personal and fun. I wouldn’t want to experience a charter any other way.
Anne

Chicago's Newest 40ft Sea Ray Sundancer Luxury Motor Yacht
Great boat and great communication with all parties. It was rainy the day that we went out on the lake but we still had such a great time.
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!
AD
Alexis

Chicago's Newest 40ft Sea Ray Sundancer Luxury Motor Yacht
We had a great time! Our charter was timely, our captain was great and our whole trip was smooth. We had a blast!
TD
Tina

Chicago's Newest 40ft Sea Ray Sundancer Luxury Motor Yacht
We had an amazing time! The entire process was easy, communication was great, and everything was exactly as described. Highly recommend for anyone looking for a fun day on the water, we'll definitely be booking again!