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Rent a Boat or Yacht in Chicago, Illinois

Page 3 of 11262 listings

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
53' Luxury Yacht w/Flybridge and Sundeck Rental in Chicago, Illinois
Events in Chicago · 12 guests

53' Luxury Yacht w/Flybridge and Sundeck Rental in Chicago, Illinois

5.0
Superowner
$375/hour
Instant Book
7 to 13 passenger Lake Michigan Sailing Charter
Sailing in Chicago · 13 guests

7 to 13 passenger Lake Michigan Sailing Charter

5.0
$550/hour
SeaRay Sundancer 35' Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 12 guests

SeaRay Sundancer 35' Motor Yacht Rental in Chicago, Illinois

4.9
$200/hour
Gorgeous Sea Ray Sundancer 40ft in Chicago with Stunning Interior
Events in Chicago · 13 guests

Gorgeous Sea Ray Sundancer 40ft in Chicago with Stunning Interior

5.0
Superowner
Best of 2025
$245/hour
'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
*** $250**Weekend Charter Rental - 33' Maxum!
Events in Chicago · 10 guests

*** $250**Weekend Charter Rental - 33' Maxum!

4.9
$175/hour
Sail & Swim from a Luxury Sailing Yacht
Sailing in Chicago · 7 guests

Sail & Swim from a Luxury Sailing Yacht

5.0
Superowner
$299/hour
Instant Book
42' Luxury Mediterranean Yacht - 3 Boats Available! Discount on Weekdays!
Events in Chicago · 12 guests

42' Luxury Mediterranean Yacht - 3 Boats Available! Discount on Weekdays!

5.0
$200/hour
39' Sea Ray Sundancer - Motor Yacht for Charter in Chicago, Illinois
Events in Chicago · 12 guests

39' Sea Ray Sundancer - Motor Yacht for Charter in Chicago, Illinois

5.0
Superowner
$250+/hour
Price Drop!!! Sunday Morning Special!!35' Luxury Motor Yacht
Events in Chicago · 12 guests

Price Drop!!! Sunday Morning Special!!35' Luxury Motor Yacht

4.5
$180+/hour
Stylish elegance and spacious comfort ... your best time ever!
Events in Chicago · 12 guests

Stylish elegance and spacious comfort ... your best time ever!

4.9
$250/hour
36ft Carver Mariner Motor Yacht in Chicago
Events in Chicago · 12 guests

36ft Carver Mariner Motor Yacht in Chicago

4.9
$350/hour
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
Calling all Aquaholics! Luxury Cruising on Lake Michigan w/ 32' Chaparral Yacht
Powerboats in Chicago · 12 guests

Calling all Aquaholics! Luxury Cruising on Lake Michigan w/ 32' Chaparral Yacht

4.9
Superowner
Best of 2025
$300/hour
Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)
Events in Chicago · 13 guests

Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)

4.9
Superowner
Best of 2025
$250/hour
38-ft Party Pontoon for Up to 20 Guests in Chicago
Powerboats in Chicago · 20 guests

38-ft Party Pontoon for Up to 20 Guests in Chicago

5.0
Superowner
Best of 2025
$700/hour
Summertime Chi Vibes - Soak up the Sun in Style!
Powerboats in Chicago · 6 guests

Summertime Chi Vibes - Soak up the Sun in Style!

5.0
$300/hour
Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
Sailing in Chicago · 3 guests

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

4.8
$120/hour
33ft Day Boat in Chicago
Events in Chicago · 10 guests

33ft Day Boat in Chicago

4.9
$375/hour
Stunning Multi-Level 47’ Carver Yacht in Chicago for up to 13 Guests
Events in Chicago · 13 guests

Stunning Multi-Level 47’ Carver Yacht in Chicago for up to 13 Guests

4.8
$300/hour
Instant Book
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
Events in Chicago · 5 guests

Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob

5.0
Superowner
$200/hour
New Spacious 40ft Cruisers Yacht for Rent in Chicago
Events in Chicago · 12 guests

New Spacious 40ft Cruisers Yacht for Rent in Chicago

5.0
Superowner
$400/hour
46ft Prestige Flybridge Luxury Yacht in Chicago
Events in Chicago · 13 guests

46ft Prestige Flybridge Luxury Yacht in Chicago

4.9
$400/hour

Chicago Reviews

  1. cf

    carolynn

    Sail & Swim from a Luxury Sailing Yacht

    This is an iconic trip in Chicago. I have always been on the river walk or on a kayak looking at people boats and thought "Those lucky kids." So this time I rented a sailboat to go out on the lake- even luckier! The operators are very organized and helpful. Everything was as expected from the site. Communication throughout was excellent. Thanks for lovely and memorable sail. I'm coming back to jump in the lake when the water temperature is a bit warmer :)

  2. Ari

    Ari

    39' Sea Ray Sundancer - Motor Yacht for Charter in Chicago, Illinois

    Captain James and Captain John were wonderful hosts. They were clear about procedures and safety that made my group feel really comfortable. The boat was clean and ready for our use. We had a great time at the playpen. I’d definitely book again if in the Chicago area. Thank you again!

  3. JF

    James

    53' Luxury Yacht w/Flybridge and Sundeck Rental in Chicago, Illinois

    Amazing boat! Clean, large, and stored at a great marina to spend time at before or after. Very professional and friendly owner. Captain Dean was our captain and made the experience really fun and safe for all. Highly recommend!

  4. AA

    Adaku

    *** $250**Weekend Charter Rental - 33' Maxum!

    We had a group of eight, and unfortunately, some of our guests were caught in traffic and running late. Mr. Diggs was incredibly understanding and communicated with us throughout, patiently waiting for everyone to arrive. Our guests were excited about swimming in the lake, but due to the slightly windy conditions, Mr. Diggs thoughtfully advised against it for our safety. Shortly after, the wind picked up, creating larger waves, and we truly appreciated his commitment to keeping us safe. Once we docked, he generously took the time to let us capture some beautiful moments with pictures before welcoming his next group.

  5. Victoria

    Victoria

    Stylish elegance and spacious comfort ... your best time ever!

    Had a cool time on the boat. The communication was quick and at a timely matter. I would suggest getting 4+ hours if you actually want time on the boat. Takes about 30+ minutes to get to and from the playpen. Thank you for a great experience

  6. Osamudiamien

    Osamudiamien

    Stunning Multi-Level 47’ Carver Yacht in Chicago for up to 13 Guests

    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.