The Best Boat Rentals in Chicago

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 :)

50' Multi-level Luxury Yacht with Party up to 12

Captain Jim and his team went above and beyond to make our charter an unforgettable experience. From the moment we departed to the smooth arrival back at the dock, everything was handled with professionalism, confidence, and a warm, friendly attitude. The boat was immaculate, the ride was smooth, and Captain Jim clearly knew the waters like the back of their hand. They made us feel safe, relaxed, and completely taken care of the entire time. Whether it was pointing out interesting sights, adjusting course for the best views, or making sure we had everything we needed on board, their attention to detail was exceptional. You can tell they truly love what they do—and it shows in the way they connect with guests and manage every aspect of the trip seamlessly. I highly recommend Captain Jim and his team, to anyone looking for a top-tier charter experience. Thank you again for an incredible day on the water!

25ft Rinker - Captained included in price- Chicago

Joe was incredible! I booked a 2 hour skyline cruise/swim time for my nephew's 8th birthday and Joe made us so comfortable. He answered all my questions about life jacket sizes and weather fluctations and adjusted our departure time to ensure we didn't get caught in a storm. Highly recommend!

Private Cruise onboard Hunter Legend Sailboat in Chicago

We had an amazing time sailing around Lake Michigan with Captain Mitch! The marina was super easy to locate/get to, the boat was the perfect size for our group of four, and we really enjoyed our time on the water. I would highly recommend booking a trip with 3rd Coast!

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

I booked this experience because Nijole had amazing reviews — and now I truly know why. She is talented, no-nonsense host who knows exactly how to make you feel comfortable when you're aboard. We could not have been more grateful or had a better time. Thank you, Nijole! A superstar.

46' Spacious Portofino Party Yacht in Chicago For Every Occasion

Had the best time out on the water with Captain Kyle! He was super professional, friendly, and made sure we felt comfortable and had fun the entire trip. The boat was clean, spacious, and had everything we needed. Kyle knew all the best spots and kept the vibe fun and relaxed. You can tell he really knows what he’s doing and loves what he does. Highly recommend booking with him — can’t wait to go out again!