Book Now  Specials
"BIG BOAT" - up to 36 people
REWARDS         Pricing / Availability


A few reviews from the many we have on yelp*

“We had an amazing time this weekend, me and my girlfriends celebrating one of the girls’ birthday. The boat we rented was fantastic but it was captain Gregg and captain Liz that made it an outstanding experience. They were so nice and friendly! They had the boat was fully equipped, with ice, cold water, coolers, cups and a very clean bathroom. Captain Liz is also a model and she takes pics like a pro, so (cherry on top of the cake) we ended the day with beautiful pics of our Sunday celebration!”
Carla E. Bluffview, Dallas, TX, 8/16/2021 yelp*
“We had an excellent charter experience with Captain Bill on a speedboat. Booking the boat was quite easy through the website, then you can contact the captain yourself to see who is available (company gives names/contact info).
I would definitely rent from CSC again. Prices were also pretty average compared to other companies! Definitely recommend.”
Gabrielle W, New Orleans, LA, 8/19/2020 yelp*

“Took a nice afternoon sail on Lake Michigan with Captain Rob. He’s very friendly, outgoing and knowledgeable about the lake, the city, sailing and a host of general topics! We had lunch and enjoyed the beautiful skyline and lively conversation! This is a terrific way to experience Chicago and the lake. The boat we chartered was clean, well-maintained and ready to accommodate your group…we had six adults.
If you are looking for a relaxing and fun way to spend some quality time in Chicago we highly recommend calling Capt. Rob and chartering a sail. Pick up a nice loaf of crusty bread, a nice selection of tasty cheese, sandwiches, some snacks and a couple bottles of wine and head down to the Belmont Harbor marina. You’ll enjoy the experience! Cheers!”

Mark M., Houston, TX 8/28/2015 yelp*
“Chicago Sailboat Charters has a gem in Captain Steve and Alison, and I’m so glad I was able to meet both of them as well as set sail on his boat. I truly am going to be organizing a group of friends to go back so they can experience the fun and knowledge of Captain Steve. I was a little afraid because the water wasn’t that calm when we went out but thankful it started to settle as we got further out and I was able to relax and laugh at the great stories that Captain Steve told us all about. Alison was always smiling and she was very helpful to us all. The cost is about 210.00 an hour with a 3 hour minimum plus tax and gratuity and up to 12 people can ride in the sailboat so that can be as little as 60 to 70 dollars a person. You can’t beat that deal!!! You are able to BYOB but no red wines I believe but don’t quote me. I wouldn’t wear flip flops and dress like I did because you want to be able to walk around and experience the sail boat. I would say shorts or pants and a pair of shoes that aren’t slippery. If you get a chance go go go and IMO Captain Steve and Alison are the best! Enjoy!”
La Tonya G., Chicago, IL 6/10/2014 yelp*
“I highly recommend this charter service, and Captain Steve is such a delight! What a man full of wit and whimsy!? You couldn’t hope for a more pleasant, refined sailing experience in Chicago with such a positive guide. I have used this service 3 times and it really does keep getting better. Last night we waited just an extra 15 minutes for the storm to pass and get the all clear, and it was truly worth the wait as the beautiful Chicago skyline was backlit by an amazing lightning show. Remarkable and beautiful!”
Coleman B., Chicago, IL 8/31/2013 yelp*
“I used Chicago Sailboat Charters as part of an engagement proposal. Marty and especially Matt were both incredibly helpful to me in planning out the afternoon and making the experience a wonderful time for my now fiance and I. I would highly recommend them to others looking for a private sail.”
Ryan Z., Washington, DC 4/28/2012 yelp*

“I bought a Groupon for my boyfriend’s birthday, and the experience was amazing. I liked that you sail in small groups and can bring wine and snacks. The view was beautiful, and the sunset was even more so. I highly recommend this excursion to anyone!”
Lissa C., Saint Louis, MO 7/18/2011 yelp*
“Love it! Love it!, I have never been sailing, thought I surprise the love of my life who LOVES sailing for our 2nd anniversary. The crew was awesome, thank you Mike & Rick for making the trip so wonderful. Perfect nite, beautiful skyline and great experience. Will definitely do it again.”
– Jesse L., Chicago, IL 7/2/2010 yelp*
“I did not get the Groupon, but it was still worth every penny. Marty was a great captain, very genuine, and accommodating. Clean boat, comfy seating, and an excellent view of the city, what more do you need? The boat was easy to find, and Marty hooks you up with free parking, which was unexpected, and appreciated.”
– Monte L., Chicago, IL 7/7/2009 yelp*
“I contacted Captain Marty at Chicago Sailboat Charters to arrange for a private charter to celebrate our wedding anniversary. The booking online feature was appealing to me, because often times it’s hard for me to use the phone during the day. From the first contact until the end of our cruise, Marty was quick to respond to our requests. He’s also very knowledgeable of sailing, Lake Michigan and the city of Chicago. Our sailing trip was a blast, I’d highly recommend Marty and Chicago Sailboat Charters.”
– Logan C., Aurora, IL 7/16/2008 yelp*