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All listings in Illinois

Incredible tours in Illinois, United States.

4.9

(5,444 Reviews)

Page 2 of 12 • 269 listings

Limited Availability

Powerboats in Chicago · 8 guests

Captained 27ft Bayliner Ciera Yacht in Chicago, Illinois

4.6

$275/hour

Events in Chicago · 13 guests

Stunning Multi-Level 47’ Carver Yacht for Summertime in Chicago

4.8

$300/hour

Limited Availability

Events in Chicago · 12 guests

SeaRay 330 Motor Yacht Charter in Chicago, Illinois for 12 Guests

5.0

$200/hour

Events in Chicago · 8 guests

Come enjoy fun in the sun on our 30ft Bayliner Ciera for 8 passengers in Chicago

4.7

$300/hour

Events in Chicago · 6 guests

Summertime Chi Vibes - Soak up the Sun in Style! 34' Cruisers South Beach Yacht

5.0

$375/hour

Limited Availability

Events in Chicago · 6 guests

New 48ft Sport Coupe Yacht in Chicago River & Lake Charter

4.9

$300/hour

Events in Chicago · 12 guests

44ft Regal Luxury Yacht Perfect for Playpen Parties and Lake Michigan Cruises!

5.0

$275+/hour

Limited Availability

Powerboats in Chicago · 10 guests

Cruisers Y3375 Express Yacht Downtown Chicago Experience

5.0

Superowner

$250/hour

Limited Availability

Events in Chicago · 12 guests

Explore the Famous Chicago Playpen! - 46ft Sea Ray Motor Yacht!

5.0

Superowner

Best of 2026

$220/hour

Instant Book

Limited Availability

Events in Chicago · 12 guests

37ft Beautiful Sea Ray Venture Motor Yacht - Explore Chicago's Famous Playpen

5.0

Superowner

Best of 2026

$220/hour

Instant Book

Events in Chicago · 7 guests

Captained 51' Sea Ray Sundancer Luxury Yacht in Chicago - 7 Guests

5.0

Superowner

$500+/hour

Limited Availability

Events in Chicago · 12 guests

Anchor in the Famous Chicago Playpen with 37' Rinker Fiesta Vee Yacht

5.0

Superowner

Best of 2026

$325/hour

Instant Book

Events in Chicago · 13 guests

Soak Up the Sun Onboard a 42' Sea Ray Express Cruiser in Chicago

5.0

$275/hour

Powerboats in Chicago · 5 guests

27ft Sea Ray Deck Boat for 5 Guests, Captain Included

5.0

$235/hour

Limited Availability

Sailing in Chicago · 6 guests

Set Sail with 36' Sailing Boat in Downtown, Chicago for 6 Guests

5.0

$225/hour

Events in Chicago · 10 guests

33ft Bayliner Powerboat Charter in Chicago for 10 Guests

4.6

$300/hour

Events in Chicago · 12 guests

Luxury 40ft Maxum 3700 SCR Motor Yacht Available To Cruise To The Playpen!

4.8

$275/hour

Limited Availability

Events in Chicago · 12 guests

Enjoy Chicago on this 46' Sea Ray - Great for Birthdays - Bachelorette Parties

5.0

Superowner

Best of 2026

$400/hour

Instant Book

Limited Availability

Events in Chicago · 13 guests

44ft Azimut Premier Party Yacht Chicago for Up to 13 - plus Jet Ski Available

5.0

Superowner

$625+/hour

Limited Availability

Sailing in Chicago · 6 guests

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

5.0

Superowner

Best of 2026

$220/hour

Limited Availability

Events in Chicago · 12 guests

46' Sunseeker Portofino Yacht in Chicago for Parties & Events

4.7

$250/hour

Limited Availability

Events in Chicago · 12 guests

Show-Stopping Lake Michigan Luxury | 36’ Regal LS36 Motor Yacht with Seakeeper

4.7

$250+/hour

Events in Chicago · 13 guests

50' Sea Ray Sundancer Motor Yacht for 13 Guests in Chicago, IL -July Promo

5.0

$375/hour

Events in Chicago · 13 guests

Multi Level 48' Carver Mariner Yacht for 13 Guests in Chicago, IL

5.0

$350/hour

Top Destinations Nearby

286
Chicago
Illinois

Tours Reviews in Illinois

WK
William

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Nijole was a wonderful captain with great communication and flexibility. The change in plans due to weather was seamless. We had a great time on the lake with Nijole, Remus and Piper and will chose her again if we are back in Chicago and want to go out for a sail. Thanks again Nijole!
Reanna

Cruisers Y3375 Express Yacht Downtown Chicago Experience
The boat day was our favorite part of our bachelorette trip. We had the best time and we loved Captain Sam! 10/10 recommend this company!
LO
Leila

37ft Beautiful Sea Ray Venture Motor Yacht - Explore Chicago's Famous Playpen
The rental was a smooth process, answered all questions very quickly. The boat was clean and captain Mike was great!!
AS
Audrey

Captained 27ft Bayliner Ciera Yacht in Chicago, Illinois
Ivan was accommodating to my desired timeframe, he ensured my group felt safe during the ride, and the whole experience was worth it. Communication is key and Ivan reassured me throughout the booking. I can definitely see myself booking with him again!
Irina

Captained 27ft Bayliner Ciera Yacht in Chicago, Illinois
Definitely recommend!Ivan is such a nice guy, he made everything to make our trip better! And the biggest plus that he picked up you on the river walk which is so nice and convenient you don’t need to go anywhere. We had dinner at RPm seafood restaurant and right after Ivan just picked up us and we were enjoying our trip on Chicago river!
Osamudiamien

Stunning Multi-Level 47’ Carver Yacht for Summertime in Chicago
Had one of the best times I’ve ever had with my closest group of friends. The boat was a beautiful piece of architecture, the captain was very nice, and being in the playpen for a few hours is something special. Can’t wait to book another boat with Tristian in the near future. My only advice to people is that if you’re considering doing this, don’t wait. Book it now.