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Rent a Boat or Yacht in Chicago, Illinois

Page 6 of 11257 listings

54ft Sea Ray Sundancer Motor Yacht
Events in Chicago · 12 guests

54ft Sea Ray Sundancer Motor Yacht

New
$725/hour
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
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
Instant Book
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
$300+/hour
Multi Level 47' Carver Yacht for 13 Guests in Chicago, IL-Reduced Price! (MPY#4)
Events in Chicago · 13 guests

Multi Level 47' Carver Yacht for 13 Guests in Chicago, IL-Reduced Price! (MPY#4)

5.0
$300/hour
27 ft Sea Ray, Captain Included
Events in Chicago · 8 guests

27 ft Sea Ray, Captain Included

5.0
$199/hour
Instant Book
40’ Cruiser Yacht Charter for fun, music and you bring the action!
Events in Chicago · 12 guests

40’ Cruiser Yacht Charter for fun, music and you bring the action!

4.4
$300/hour
Experience Lake Michigan like never before on Beautiful 35ft Maxum
Events in Chicago · 10 guests

Experience Lake Michigan like never before on Beautiful 35ft Maxum

5.0
$225/hour
Summertime Chi Ready!!
Events in Chicago · 12 guests

Summertime Chi Ready!!

5.0
$300/hour
46' Azimut Quartano Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 13 guests

46' Azimut Quartano Motor Yacht Rental in Chicago, Illinois

5.0
$650/hour
Instant Book
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
Relax And Enjoy This Beautiful Carver Yacht
Events in Chicago · 12 guests

Relax And Enjoy This Beautiful Carver Yacht

5.0
$375/hour
33' Luxury Rinker Fiesta Vee 330 w/ Premium Sound
Events in Chicago · 10 guests

33' Luxury Rinker Fiesta Vee 330 w/ Premium Sound

5.0
$225/hour
Enjoy the Sun with Family or Friends on a 58' SeaRay Sundancer
Events in Chicago · 12 guests

Enjoy the Sun with Family or Friends on a 58' SeaRay Sundancer

5.0
$350/hour
Mediterranean Yacht with Fly bridge Boat
Events in Chicago · 12 guests

Mediterranean Yacht with Fly bridge Boat

5.0
$400/hour
Instant Book
Chicago Luxury Boat Rental
Events in Chicago · 10 guests

Chicago Luxury Boat Rental

5.0
$225/hour
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
$300/hour
33ft Maxum Scr - Your Next Charter Awaits You!
Events in Chicago · 12 guests

33ft Maxum Scr - Your Next Charter Awaits You!

5.0
$300/hour
50ft Spectacular Luxury Italian Unique Yacht
Events in Chicago · 13 guests

50ft Spectacular Luxury Italian Unique Yacht

5.0
$400/hour
Chicago Boat Cruise on Captained Sea Ray Sundancer 260 Motor Yacht
Events in Chicago · 8 guests

Chicago Boat Cruise on Captained Sea Ray Sundancer 260 Motor Yacht

5.0
$275/hour
51ft Sea Ray Sundancer Yacht at Diversey Harbor!
Events in Chicago · 12 guests

51ft Sea Ray Sundancer Yacht at Diversey Harbor!

5.0
$600/hour
47' Carver "Pier Pressure" Chicago, IL
Events in Chicago · 13 guests

47' Carver "Pier Pressure" Chicago, IL

New
$728/hour
63ft Premier Sea Ray Chicago Playpen, River, Winery
Events in Chicago · 12 guests

63ft Premier Sea Ray Chicago Playpen, River, Winery

5.0
Superowner
$700/hour
Instant Book
Tiki Themed Party Boat, 18-36 Guests, captain, crew & beverage package included.
Events in Chicago · 36 guests

Tiki Themed Party Boat, 18-36 Guests, captain, crew & beverage package included.

5.0
$1,350/hour

Chicago Reviews

  1. TI

    Tariq

    51ft Sea Ray Sundancer Yacht at Diversey Harbor!

    Can’t speak highly enough about the professionalism. The captain prioritized our safety, communicated clearly, and made sure everything ran smoothly from start to finish. It was my first time, and I couldn’t have asked for a better experience — truly 10/10 across the board. Grateful and impressed! He also made us feel completely at home and comfortable throughout the entire trip. I’ll definitely be booking with him every time. The boat was exactly as advertised — clean, spacious, and just what we were looking for. Highly recommend!

  2. CE

    Cheryl

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

    Had the best time on the boat. The whole team was incredible. They were friendly, patient and the group had a blast. Our boat day really made the entire weekend. Would 10/10 recommend and will be using them again!

  3. HK

    Hanna

    Tiki Themed Party Boat, 18-36 Guests, captain, crew & beverage package included.

    This was the perfect boat for our bach party group of 23 people! There was plenty of space for everyone, with the amazing top deck (with tables and chairs!), the back deck, and the indoor bar and "dining" area. Captain Blue was great at communication leading up to the day, and the whole crew made us feel welcome and celebrated. Especially with the bar included, this is an AMAZING value! You won't regret it.

  4. Kaliyah

    Kaliyah

    33' Luxury Rinker Fiesta Vee 330 w/ Premium Sound

    Amazing crew and captain! Boat was super clean and comfy. The captain kept us extremely safe and made sure we had fun! After being cancelled on by two other people. Will book with them over and over again.

  5. M

    Mark

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

    Another Great Day on the Water This was my second trip with Captain Russell, and it won’t be my last. The boat is better than advertised — super clean and comfortable. Captain Russell just makes it easy. He knows what he’s doing, keeps everything relaxed, and makes you feel like you’ve got your own personal captain for the day. Always a great time out on the lake with him.

  6. KA

    Kelly

    27 ft Sea Ray, Captain Included

    Bobby was the best captain! We left right on time and the water was beautiful. He had a cooler with ice prepared and ready for us upon arrival, and made the whole trip a time to remember! I could not recommend him enough!