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Page 2 of 10 • 240 listings
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Makaeda
Luxury 35' Silverton 330 Sport Bridge Yacht Rental in Chicago!
This was our groups first experience in Lake Michigan. The waves were definitely something we’ve never experienced but the hospitality from Mike, Tony and the crew was amazing they were very warm and welcoming and we had a great time during our trip. We would definitely book with them again and recommend.
OT
Olivia
Fantastic Experience with Peter and Team! Peter was incredible—he even met us in the parking lot with a wagon to help transport our drinks and food. He was extremely friendly and communicative from start to finish. My coworkers and I had an amazing time cruising around the lake. The only minor downside was needing to bring our own ice, but everything else was absolutely 10/10. We’ll definitely be booking with Peter and his team again!
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carolynn
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 :)
RJ
Rachel
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!
MA
Mahab
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!
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James
53' Luxury Yacht w/Flybridge and Sundeck Rental in Chicago, Illinois
Amazing boat! Clean, large, and stored at a great marina to spend time at before or after. Very professional and friendly owner. Captain Dean was our captain and made the experience really fun and safe for all. Highly recommend!