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Page 10 of 10 • 240 listings
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Washington
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Caley
Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
Amazing time! Ben is a very experienced and knowledgeable captain , he taught us how to steer the boat and answered all our questions. Hes very nice and made the ride great! You also get an amazing view of the city that you can’t get anywhere else I brought my boyfriend as a birthday present and it was perfect!

Ravid
38-ft Party Pontoon for Up to 20 Guests in Chicago
My friends and I had an amazing time on Captain Greg's boat! The boat had speakers, cooler, a bathroom, floaties, pretty much everything we needed. The boat was very spacious and comfortable. The crew were very friendly and welcoming as well! We had so much fun sailing around Chicago and swimming in the lake, it was a perfect boating experience!
EW
Emma
24 Passenger Captained Party & Event Boat in Chicago!
We had a great time on our excursion. They let us pick where we wanted to go and what we wanted to do, and had everything we needed on the boat. The boat itself was clean and safe and had plenty of room for 16 of us to comfortably move around. Would definitely use them again.
KC
Karen
Luxury 29ft Crownline Bowrider 285 SS
Mark's boat was perfect for our mommy-daughter night for fireworks. The girls had an absolute blast swimming and jumping in/out of the mesh floaty. My daughter asked when we are renting Mark's boat again. Captain Edward was amazing. We couldn't have asked for a more perfect night on the boat in the best city in the world. Thanks Mark for making it so easy. We can't wait to return.
dr
david
Set Sail with 36' Sailing Boat in Downtown, Chicago
Went on a 3 hour cruise with Captain Dawn and Ted and wow did we have a great time. It’s well worth it to see Chicago from the lake, and no better way to get out on the water than on a sailboat. Will definitely reach out to this group again when I return to Chicago.
RJ
Robert
Set Sail with 36' Sailing Boat in Downtown, Chicago
Ray and Cassidy were great! We didn't have a planned route or destination so Ray chose his own and it was incredible! The views were amazing and we had the best seats in the house to the Air and Water show! Ray and Cassidy were both friendly and knowledgeable through the whole experience. We couldn't have asked for a better crew! The boat was beautiful and a couple of us even had a chance to steer it. All around amazing.