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Rent a Boat or Yacht in Chicago, Illinois

Page 1 of 9194 listings

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing in Chicago · 6 guests

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

5.0
Superowner
$220/hour
Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Best of 2025
$200/hour
High Demand
27' Chris Craft with Water Toys plus Jet Ski Available
Powerboats in Chicago · 6 guests

27' Chris Craft with Water Toys plus Jet Ski Available

4.9
Superowner
$240/hour
High Demand
2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!
Events in Chicago · 11 guests

2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!

5.0
$250/hour
High Demand
Captained Charter on 60ft Martini Sea Ray Luxury Motor Yacht in Chicago
Events in Chicago · 20 guests

Captained Charter on 60ft Martini Sea Ray Luxury Motor Yacht in Chicago

4.7
$1,500/hour
Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat
Sailing in Chicago · 6 guests

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

5.0
$225/hour
High Demand
'The Gwen' 38’ Carver Mariner Captained Charter with all amenities in Chicago!
Events in Chicago · 13 guests

'The Gwen' 38’ Carver Mariner Captained Charter with all amenities in Chicago!

4.9
Superowner
$275/hour
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
Superowner
$200+/hour
High Demand
'Aquaholic' 40' Sea Ray Captained Charter on with all amenities in Chicago!
Events in Chicago · 13 guests

'Aquaholic' 40' Sea Ray Captained Charter on with all amenities in Chicago!

5.0
Superowner
$350/hour
Limited Availability
27' Maxum 2400 Motor Yacht Rental in Chicago
Powerboats in Chicago · 8 guests

27' Maxum 2400 Motor Yacht Rental in Chicago

4.3
$300/hour
High Demand
Double Decker 50ft Sea Ray Flybridge Yacht!
Events in Chicago · 13 guests

Double Decker 50ft Sea Ray Flybridge Yacht!

5.0
Superowner
Best of 2025
$292/hour
Set Sail with 36' Sailing Boat in Downtown, Chicago
Sailing in Chicago · 6 guests

Set Sail with 36' Sailing Boat in Downtown, Chicago

5.0
$225/hour
High Demand
Stunning 105ft Denison Party Yacht in Chicago
Events in Chicago · 30 guests

Stunning 105ft Denison Party Yacht in Chicago

4.5
$1,450+/hour
Limited Availability
Enjoy Chicago in this 45' Sea Ray Express Cruiser Yacht - Perfect for Parties!
Events in Chicago · 12 guests

Enjoy Chicago in this 45' Sea Ray Express Cruiser Yacht - Perfect for Parties!

4.9
Superowner
Best of 2025
$400/hour
Instant Book
Limited Availability
28ft. Sea Ray Captained Boat Rental in Chicago
Events in Chicago · 6 guests

28ft. Sea Ray Captained Boat Rental in Chicago

5.0
Superowner
$225/hour
High Demand
LUXURY - Spacious, Clean 40' Cruiser's Yacht (Super Owner) in Chicago, IL!!
Events in Chicago · 12 guests

LUXURY - Spacious, Clean 40' Cruiser's Yacht (Super Owner) in Chicago, IL!!

5.0
Superowner
$300+/hour
High Demand
Luxurious 60FT Azimut | Double-deck Yacht
Events in Chicago · 13 guests

Luxurious 60FT Azimut | Double-deck Yacht

5.0
Superowner
Best of 2025
$750/hour
Limited Availability
Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.
Sailing in Chicago · 6 guests

Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.

5.0
$450/hour
Limited Availability
31' Captained Sea Ray Sundancer, Fun in Chicago Aboard
Powerboats in Chicago · 6 guests

31' Captained Sea Ray Sundancer, Fun in Chicago Aboard

4.9
$250/hour
Limited Availability
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
Limited Availability
Luxury 40-foot Yacht available to cruise to the Playpen!
Powerboats in Chicago · 12 guests

Luxury 40-foot Yacht available to cruise to the Playpen!

4.8
$295/hour
High Demand
31' Sea Ray Romantic or Family or Fun Getaway  Waiting for you !!!
Events in Chicago · 6 guests

31' Sea Ray Romantic or Family or Fun Getaway Waiting for you !!!

5.0
$350/hour
High Demand
Spacious Crusing Yacht 40' on the Chicago Lakefront $275.00 per Hour Weekdays
Events in Chicago · 12 guests

Spacious Crusing Yacht 40' on the Chicago Lakefront $275.00 per Hour Weekdays

5.0
$275/hour
Limited Availability
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

Chicago Reviews

  1. ED

    Emma

    28ft. Sea Ray Captained Boat Rental in Chicago

    I can’t recommend Captain Memo enough! Not only did he go above and beyond to make my husband and I’s afternoon on his boat an awesome experience, he is also the kindest human! We had so much fun and will definitely be using him again. If you are looking for great captain, he is your guy!

  2. Shannon

    Shannon

    'The Gwen' 38’ Carver Mariner Captained Charter with all amenities in Chicago!

    This was our second year in a row booking this boat. They have consistently delivered the best customer service. I have been renting yachts for years and this is the only boat to provide ice and water making the experience very comfortable. I couldn’t recommend them enough!

  3. VJ

    Vanessa

    28ft. Sea Ray Captained Boat Rental in Chicago

    There’s not enough words to describe how great our experience was with Captain Memo. His communication was great. He was very knowledgeable of the water. Made our experience very memorable. If you’re looking to experience a wonderful yacht day Book now!!! Thank you Memo for going over and beyond to make sure we felt safe and have good time!!

  4. Issam

    Issam

    28ft. Sea Ray Captained Boat Rental in Chicago

    ⭐️⭐️⭐️⭐️⭐️ We recently had the pleasure of going on a boat tour with Captain Nemo in Chicago, and we can't recommend it highly enough! From the moment we stepped aboard, Captain Nemo made us feel like family. The views of the skyline from the water were absolutely breathtaking, and the boat itself was comfortable and well-maintained. Captain Nemo's attention to detail and commitment to ensuring we had the best experience possible really stood out. Whether you’re a local or just visiting, this tour is a must-do! Thank you, Captain Nemo, for an unforgettable day on the water!

  5. ZD

    Zinnia

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

    Amazing experience with top-notch communication from start to finish. Super responsive and incredibly knowledgeable—especially helpful for first-timers in Chicago. They guided us around the lake and to the perfect fireworks viewing spot, even capturing great photos for us. The captain was skilled and professional, and the music made the ride even better. Highly recommend!

  6. brett

    brett

    31' Sea Ray Romantic or Family or Fun Getaway Waiting for you !!!

    Rick was amazing. If I do this again, I will be looking to book with Rick. We had an amazing day in the playpen. Sound system on board is awesome. Rick made everything very easy for us. Great communication. Easy to get to his boat. Overall great experience and highly recommend.