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Rent a Boat or Yacht in Chicago, Illinois

Page 9 of 11264 listings

32' Bayliner Avanti for up to 12 people
Events in Chicago · 12 guests

32' Bayliner Avanti for up to 12 people

5.0
$300/hour
Instant Book
Experience Luxury and Adventure on a 33' Sea Ray Sundancer Yacht in Chicago
Events in Chicago · 10 guests

Experience Luxury and Adventure on a 33' Sea Ray Sundancer Yacht in Chicago

5.0
$350/hour
68' Luxurious Private Yacht Charters in Chicago
Events in Chicago · 45 guests

68' Luxurious Private Yacht Charters in Chicago

5.0
$1,750/hour
Chicago Private Boat Rental - Explore Chicago's Skyline and Waters - SUCESSION
Events in Chicago · 12 guests

Chicago Private Boat Rental - Explore Chicago's Skyline and Waters - SUCESSION

5.0
$315/hour
Instant Book
Beautiful Sea Ray 320 Sundancer Inboard Boat
Events in Chicago · 10 guests

Beautiful Sea Ray 320 Sundancer Inboard Boat

New
$225/hour
20' Lund Bass Boat for 3 in Chicago, Illinois
Fishing in Chicago · 3 guests

20' Lund Bass Boat for 3 in Chicago, Illinois

5.0
$67/hour
40ft Carver Mariner Motor Yacht Charter in Chicago, IL
Events in Chicago · 13 guests

40ft Carver Mariner Motor Yacht Charter in Chicago, IL

New
$745/hour
Explore the Chicago Playpen! 46ft Sea Ray - Lily Pad Included!
Powerboats in Chicago · 12 guests

Explore the Chicago Playpen! 46ft Sea Ray - Lily Pad Included!

New
Superowner
Best of 2025
$400/hour
42ft Sea Ray in Chicago, Burnham Harbor (Up to 12 guests)
Events in Chicago · 12 guests

42ft Sea Ray in Chicago, Burnham Harbor (Up to 12 guests)

New
$300/hour
Anchor in the Famous Chicago Playpen - 37' Rinker Fiesta Vee
Powerboats in Chicago · 12 guests

Anchor in the Famous Chicago Playpen - 37' Rinker Fiesta Vee

New
Superowner
Best of 2025
$325/hour
Luxury 43ft Azimut Atlantis Yacht Charter in Chicago, Illinois
Events in Chicago · 12 guests

Luxury 43ft Azimut Atlantis Yacht Charter in Chicago, Illinois

New
$500+/hour
Lake Michigan Chicago Yacht Party – 40' Luxury Sea Ray for Up to 12 Guests
Events in Chicago · 12 guests

Lake Michigan Chicago Yacht Party – 40' Luxury Sea Ray for Up to 12 Guests

5.0
$225/hour
Instant Book
Experience Lake Michigan like never before!!!!!
Events in Chicago · 8 guests

Experience Lake Michigan like never before!!!!!

New
$225/hour
42' Sea Ray Sundancer Luxury Yacht - Great for outings! DIVERSEY HARBOR
Events in Chicago · 12 guests

42' Sea Ray Sundancer Luxury Yacht - Great for outings! DIVERSEY HARBOR

2.7
$150/hour
Instant Book
Catamaran Sailing Lessons Chicago
Tours in Chicago · 6 guests

Catamaran Sailing Lessons Chicago

New
Best of 2025
$350+/hour
55' Sea Ray Motor Yacht Bareboat Charter in Chicago
Events in Chicago · 12 guests

55' Sea Ray Motor Yacht Bareboat Charter in Chicago

New
$1,337/hour
Italian Luxury Azimut 63ft Yacht - 12 Guests - Chicago
Events in Chicago · 12 guests

Italian Luxury Azimut 63ft Yacht - 12 Guests - Chicago

New
$800/hour
26’ Sea Ray 240 Sundeck
Powerboats in Chicago · 10 guests

26’ Sea Ray 240 Sundeck

New
$225/hour
Instant Book
40' Cruisers Yachts "Bad Boys II" Chicago, IL
Events in Chicago · 13 guests

40' Cruisers Yachts "Bad Boys II" Chicago, IL

New
$818/hour
45' Cruiser Yacht "MoEz Chilli'n" Chicago, IL
Events in Chicago · 13 guests

45' Cruiser Yacht "MoEz Chilli'n" Chicago, IL

New
$1,089/hour
34' Luxury Sea Ray Sundancer Yacht Rental in Chicago, Illinois
Events in Chicago · 12 guests

34' Luxury Sea Ray Sundancer Yacht Rental in Chicago, Illinois

New
$339+/hour
44 foot Cabin Cruiser for rent in Chicago $250/hr
Events in Chicago · 12 guests

44 foot Cabin Cruiser for rent in Chicago $250/hr

5.0
$350/hour
Beautiful 40ft Sea Ray Yacht
Events in Chicago · 12 guests

Beautiful 40ft Sea Ray Yacht

New
$250/hour
62' Azimut Flybridge Italian Luxury Yacht for Rent (MPY#6) in Chicago, Illinois
Events in Chicago · 13 guests

62' Azimut Flybridge Italian Luxury Yacht for Rent (MPY#6) in Chicago, Illinois

New
$800/hour

Chicago Reviews

  1. Husein

    Husein

    20' Lund Bass Boat for 3 in Chicago, Illinois

    I honestly didn’t expect to walk away from this trip with a whole new hobby, but here I am—hooked for life. Guy has this way of making the entire experience feel effortless and exciting, whether you’re a total beginner or someone who’s been at it for years. From teaching the basics with real patience to creating an atmosphere that’s both laid-back and full of energy, he made it easy to fall in love with fishing. The way he explained the gear, read the water, and shared his stories made every moment out there on the water feel like something special. You can tell he truly loves what he does, and that kind of passion is contagious. I went in thinking this was just a one-time adventure, but now I’m already planning my next trip—and buying my own gear. Can’t thank Guy enough for turning what was supposed to be a relaxing weekend into the start of a lifelong obsession. If you’ve ever been on the fence about trying fishing, let Guy be the reason you dive in—you won’t regret it.

  2. MH

    Mary Bev

    20' Lund Bass Boat for 3 in Chicago, Illinois

    Thanks for a great day on the water, Capt. Guy! We had a phenomenal morning, and we hope to fish with you again soon! Great variety of salmon & steelhead. 10/10 recommend

  3. Jahkayah

    Jahkayah

    Chicago Private Boat Rental - Explore Chicago's Skyline and Waters - SUCESSION

    What a fantastic experience! I rented Alex's boat yesterday and had an absolute blast with my group of 12 friends. From the moment we arrived, Alex was super friendly and welcoming. He showed us around the boat and made sure we felt comfortable and at ease. The boat itself was immaculate - clean, well-maintained, and organized to perfection. Alex had thought of everything to ensure our day on the water was stress-free and enjoyable. His assistant was also super helpful in getting us settled and answering any questions we had. Alex himself was an absolute pleasure to be around. He was knowledgeable about the area and gave us great recommendations for things to do and see. His enthusiasm was infectious, and he really made us feel like we were part of his own little crew. We had an amazing time cruising around the water, taking in the sights, and enjoying each other's company. The boat handled beautifully, and we were able to fit all 12 of us comfortably. Overall, I would highly recommend renting from Alex. His attention to detail, warm hospitality, and love for boating make for a truly unforgettable experience. We can't wait to come back and do it again!

  4. LL

    Lindsey

    Experience Luxury and Adventure on a 33' Sea Ray Sundancer Yacht in Chicago

    This trip was extremely easy and fun. Hans was so kind, and made sure our group was having a good time by going above and beyond and accommodating to us during a busy air and water show weekend. Could not recommend this booking more!!

  5. KG

    Karan

  6. JC

    James

    42' Sea Ray Sundancer Luxury Yacht - Great for outings! DIVERSEY HARBOR

    Boat is showing wear but nothing negative to say about the experience. Captain was prompt on departure/arrival times. Found email to be the best way of contacting.