Awesome sloop rentals near Chicago, Illinois.

Average of 14 reviews in this area.
3 listings

Sail the waters near Chicago, Illinois onboard a sloop rental.

Looking for a memorable boating experience in Chicago, Illinois? Sloops are smaller sailing boats, with a single mast. They are great boats to learn how to sail on, or to enjoy a relaxing day on the water. Enjoy the breeze and the waves on your private sloop charter, or book a rental with your sailing buddies. A captain and crew can help you sort out the perfect itinerary for your boat day. Rent a sloop in Chicago, Illinois and enjoy your time out on the waves.

Using GetMyBoat to rent your next sloop.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

GetMyBoat customer reviews for Sloop in Chicago.

  1. RL
    Charter a 31' Pearson Cruising Sloop, Chicago

    This experience was amazing. Captain Joey took us to a thrilling tour around the lake ending in a beautiful sunset with a great view. The boat and Joey was a complete fun experience catered to our needs. A chill trip all around with great moments! Worth every penny. If you have a fun group, captain Joey will fit right in and make everything fun. 12/10 recommend!!

  2. MT
    Charter a 31' Pearson Cruising Sloop, Chicago

    Had a great first sailing experience with Captain Joey! Before the outing, I was very impressed by his clear and prompt communication, especially with our concerns about the weather. We are also not from the area and he gave us clear instruction, making it easy to find him. Additionally, he was very friendly and our group very much enjoyed our sail with him and appreciated his flexibility with the timing. If we had the chance to sail in Chicago again, we would definitely call Captain Joey first!

  3. JK
    Charter 31' Hunter Sloop In Chicago, Illinois

    Barb was hands down amazing!!! I truly loved the entire day out on the boat and will be booking with her again! It is awesome to have had the opportunity to sail with her and have fun with friends!

  4. LK
    Affordable Luxury Aboard the S/V Nightswimming

    Captain C was amazing! Always enjoy getting out on the water and enjoying the view, especially on a great boat with great service. Would definitely sail again.

  5. LC
    Affordable Luxury Aboard the S/V Nightswimming

    I highly recommend Captain C!!! He is so enthusiastic and very friendly, our experienced with sailing has exceeded our expectation. PS he got a bad ass boat.

  6. MB
    Charter a 31' Pearson Cruising Sloop, Chicago

    Captain Joey was awesome! Highly recommended :)