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Browse Illinois Boat Rentals.

Page 13 of 13304 listings

2023 21' Sea-Doo Switch Pontoon Boat Rental in Carpentersville, IL (Seats 8)
Powerboats in Illinois · 8 guests

2023 21' Sea-Doo Switch Pontoon Boat Rental in Carpentersville, IL (Seats 8)

5.0
Snoozed - Active 16 Apr 2025
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
Superowner
Snoozed - Active 17 Mar 2025
50' Sea Ray Sundancer (KMB #1) - Perfect for Parties!
Events in Chicago · 12 guests

50' Sea Ray Sundancer (KMB #1) - Perfect for Parties!

4.7
Superowner
Snoozed - Active 30 Jun 2025
50' Sea Ray Yacht (KMB #2) - Perfect for Parties!
Events in Chicago · 12 guests

50' Sea Ray Yacht (KMB #2) - Perfect for Parties!

4.8
Superowner
Snoozed - Active 30 Jun 2025
72ft Private Luxury Yacht for 49 Passengers or Fewer in Chicago, Illinois
Events in Chicago · 49 guests

72ft Private Luxury Yacht for 49 Passengers or Fewer in Chicago, Illinois

4.6
Superowner
Snoozed - Active 09 Aug 2025
46' Sea Ray Express (KMB #9) - Perfect for Parties!
Events in Chicago · 12 guests

46' Sea Ray Express (KMB #9) - Perfect for Parties!

New
Superowner
Snoozed - Active 30 Jun 2025
55' Sea Ray Sundancer (KMB #19) - Luxury Yacht
Events in Chicago · 12 guests

55' Sea Ray Sundancer (KMB #19) - Luxury Yacht

New
Superowner
Snoozed - Active 30 Jun 2025
46’ Sea Ray (KMB #8) - Perfect for Parties!
Events in Chicago · 12 guests

46’ Sea Ray (KMB #8) - Perfect for Parties!

5.0
Superowner
Snoozed - Active 30 Jun 2025
37' Sea Ray (KMB#14) - Affordable Yacht for 12!
Events in Chicago · 12 guests

37' Sea Ray (KMB#14) - Affordable Yacht for 12!

New
Superowner
Snoozed - Active 30 Jun 2025
46’ Sea Ray Express (KMB #16) - Perfect for Parties!
Events in Chicago · 12 guests

46’ Sea Ray Express (KMB #16) - Perfect for Parties!

New
Superowner
Snoozed - Active 30 Jun 2025
48' Sea Ray Flybridge (KMB #6) - Luxury Flybridge Yacht!
Events in Chicago · 12 guests

48' Sea Ray Flybridge (KMB #6) - Luxury Flybridge Yacht!

2.0
Superowner
Snoozed - Active 30 Jun 2025
70' Sea Ray (KMB#18) - Luxury Yacht
Events in Chicago · 12 guests

70' Sea Ray (KMB#18) - Luxury Yacht

New
Superowner
Snoozed - Active 30 Jun 2025
56' Sea Ray Sundancer (KMB #13) - Luxury Yacht
Events in Chicago · 12 guests

56' Sea Ray Sundancer (KMB #13) - Luxury Yacht

New
Superowner
Snoozed - Active 30 Jun 2025
34’ Rinker (KMB #11) - Affordable Yacht for 12!
Events in Chicago · 12 guests

34’ Rinker (KMB #11) - Affordable Yacht for 12!

New
Superowner
Snoozed - Active 30 Jun 2025
50’ Sea Ray Yacht (KMB #3) - Perfect for Parties!
Events in Chicago · 12 guests

50’ Sea Ray Yacht (KMB #3) - Perfect for Parties!

New
Superowner
Snoozed - Active 30 Jun 2025
33' Rinker (KMB #5) - Affordable Yacht for 12!
Events in Chicago · 12 guests

33' Rinker (KMB #5) - Affordable Yacht for 12!

New
Superowner
Snoozed - Active 30 Jun 2025

Illinois Reviews

  1. AD

    Alejandro

    Charter a 31' Pearson Cruising Sloop, Chicago

    Great overall experience. I must advice that I had to adjust my plans from what I initially had in mind. I had to get props for the experience on my own, which complicated the planning and fortunately resulted all right. Also, it wasn’t until after booking my experience that I realized that Captain Joey was thinking of going out for a motorboat ride rather than for a sail, which would’ve been a total bummer - I had to talk him into this plan and he kindly agreed to doing so.

  2. SV

    Sabrina

    Charter a 31' Pearson Cruising Sloop, Chicago

    Captain Joey is incredible. He went above and beyond to ensure that my partner and I had perfect wedding portraits. He perfectly mapped out sunset and found us the perfect views. Would not have been possible without out Joey! Cant wait to come back again soon!

  3. Anthony

    Anthony

    Charter a 31' Pearson Cruising Sloop, Chicago

    I contacted Captain Joey back in February of 2022 for a June 2022 engagement charter. Long story short, my partner said YES! Everything about the trip was amazing with the only exception being that I got motion sickness about 20 minutes into the charter (be sure to take CJ’s advice when he talks to you about what to do to prevent this). CJ is a very laid-back, jokster type who really put me at ease while I was: 1. overcoming motion sickness and 2. Preparing to propose to my partner. He is batting 1000 when it comes to engagement charters so I’ve you’re looking to propose on a boat, CJ is your captain!

  4. AM

    Andrew

    Charter a 31' Pearson Cruising Sloop, Chicago

    I booked this rental for a surprise wedding engagement and Captain Joey did a great job working with me. He helped come up with game plan to pop the question and he was easy to work with even when plans changed. He was also nice enough to play along with the charade before the question was asked to keep it a surprise. I was very happy with how everything turned out and would definitely recommend to others.

  5. LK

    Linda

    Charter a 31' Pearson Cruising Sloop, Chicago

    We chose Captain Joey for my first sail. There were 4 of us, plus our experienced captain. We had a 2 hour sail and he took us by motor power inside the breakwater and then outside the breakwater for sailing. It was everything I thought it would be - peaceful and a fresh breeze with beautiful views of the Chicago skyline. I would do it again, and I highly recommend it!

  6. Cassie

    Cassie

    Charter a 31' Pearson Cruising Sloop, Chicago

    Our group of 5 ladies had a wonderful time on Lake Michigan with Captain Joey! The sailboat is beautiful, spacious and well maintained. From the directions to the dock to the actual sailing, Captain Joey knew how to make our trip great experience. The option to bring on drinks and snacks was very nice, and we enjoyed using the “picnic table” on the deck. This is a great way to enjoy the beautiful summer weather outdoors any time, but especially during the pandemic. We felt very safe on this private charter. We highly recommend sailing with Captain Joey!