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All listings in Illinois

Awesome water taxi trips in Illinois, United States.

4.7

(571 Reviews)

Page 1 of 2 • 38 listings

Events in Chicago · 8 guests

Luxury 31ft Bayliner 3055 Ciera for your Playpen Party

5.0

$180/hour

Powerboats in Chicago · 12 guests

Relax and Enjoy Aboard this 51' Sea Ray Sundancer Yacht at Diversey Harbor

5.0

Superowner

Best of 2026

$255/hour

Sailing in Chicago · 3 guests

Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor

4.8

$107+/hour

Events in Chicago · 12 guests

Top of the line Sea Ray Sundancer 340 Motor Yacht - Accommodate 12 Guests

3.8

$250/hour

Limited Availability

Events in Chicago · 13 guests

Book "After Hours" today! Sea Ray Sundancer 40ft Motor Yacht In Chicago

5.0

Superowner

Best of 2026

$225+/hour

Sailing in Chicago · 6 guests

Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat

5.0

$225/hour

Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5

$200+/hour

Sailing in Chicago · 6 guests

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

5.0

$225/hour

Limited Availability

Powerboats in Chicago · 16 guests

16 Passenger Captained Party & Event 32ft Pontoon Boat in Chicago, Illinois!

New

Superowner

Best of 2026

$650/hour

Limited Availability

Events in Chicago · 12 guests

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

4.7

$250+/hour

Limited Availability

Powerboats in Chicago · 10 guests

25ft Yamaha 252SE Jet Boat Charter in Chicago - Playpen Adventure

5.0

$245/hour

Events in Chicago · 6 guests

31ft Sea Ray Motor Yacht Chicago Romantic Family Getaway!

5.0

$350/hour

Limited Availability

Powerboats in Chicago · 24 guests

24 Passenger Captained Pontoon Boat - Fridays and Sunday Fundays in Chicago!

5.0

Superowner

Best of 2026

$800/hour

Limited Availability

Powerboats in Chicago · 10 guests

Cruise on the New & Luxurious 2024 30ft Chaparral Motor Yacht in Chicago!!!

5.0

$250/hour

Limited Availability

Events in Chicago · 12 guests

63ft Premier Sea Ray Sundancer Yacht Perfect for Chicago Playpen, River, Winery

5.0

Superowner

$700/hour

Powerboats in Fox Lake · 14 guests

24ft South Bay Tritoon on Fox Lake - Perfect for Groups up to 14

5.0

$145/hour

Limited Availability

Events in Chicago · 12 guests

42' Mediterranean Yacht for Luxury Cruises in Chicago - 3 Boats Available!

5.0

$350/hour

Limited Availability

Powerboats in Chicago · 36 guests

50ft Skipperliner Tiki Pontoon Cruise in Chicago with Beverage Package

4.5

$1,350/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

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 · 6 guests

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

5.0

$200/hour

Limited Availability

Powerboats in Chicago · 8 guests

Party Chicago Fun Lake River aboard 27ft Xperience Tritoon

5.0

$200/hour

Events in Chicago · 13 guests

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

5.0

$750/hour

Limited Availability

Events in Chicago · 13 guests

Gorgeous 61’ Sunseeker Predator Motor Yacht with Floating island in Chicago

4.8

Superowner

$275/hour

Top Destinations Nearby

286
Chicago
Illinois

Water Taxi Reviews in Illinois

EE
Emma

24 Passenger Captained Pontoon Boat - Fridays and Sunday Fundays in Chicago!
Such clear communication and made sure we had the best time!!
Gia

Book "After Hours" today! Sea Ray Sundancer 40ft Motor Yacht In Chicago
Amazing boat, we had the best time.
Mark

Luxury 31ft Bayliner 3055 Ciera for your Playpen Party
Ali was EXCEPTIONAL with the logistics, and Captain Z was AWESOME with the boating!!! We had group of five, and the accommodations fit our group exceptionally well. Our only regret is that the four hours went by so fast! lol! Highly recommend, and will DEFINITELY keep him in mind for the next excursion!
AJ
Amy

Luxury 31ft Bayliner 3055 Ciera for your Playpen Party
We had a great experience with Captain Z! He and the owner were very accommodating and communication was easy. The boat fit our party of 8. There was a good storage area in the cabin downstairs with a restroom on board. Coolers were provided for our food and beverages. We appreciated that fuel was included in the total cost. We enjoyed cruising around and spending time at the playpen with the beautiful Chicago skyline in the background!
Julian

Luxury 31ft Bayliner 3055 Ciera for your Playpen Party
I recently had the pleasure of experiencing this boat trip with Captain Z and I can't say enough about how wonderful it was! From start to finish, Captain Z was an exceptional host, making sure every detail was taken care of. The boat itself equipped with everything we needed for a perfect day on water. They were friendly, attentive, and made everyone on board feel welcome and comfortable. We had so much fun exploring the beautiful scenery, enjoying the water and relaxing on the deck. I highly recommend for anyone looking for a memorable and enjoyable boat trip.
CM
Caley

Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor
Amazing time! Ben is a very experienced and knowledgeable captain , he taught us how to steer the boat and answered all our questions. Hes very nice and made the ride great! You also get an amazing view of the city that you can’t get anywhere else I brought my boyfriend as a birthday present and it was perfect!