I booked with this company for my birthday and everything was perfect ! I booked my reservation over the phone, and the staff was really helpful with answering questions and explaining things to me. The day of I received a text from the company to contact my captain when I arrived at the dock. Captian Bill and Ava were amazing !! They were so friendly and made sure everything went seamlessly. They were so accommodating and just made everything better. Book with this company, they are professional, efficient and friendly! After posting my photos I’m getting so many inquires, I will be referring everyone I know to this company !

Had an amazing sail for my birthday. Captain Rob was fantastic and made our experience epic! I would highly recommend booking this for a special occasion.

My husband and I had a great experience on today’s 2hr sailboat ride. Dennis was our captain and was very informative, friendly, and put safety first. I would highly recommend this company and already told my husband that I want to do this again for my birthday with our friends!

I recently planned a bachelorette party for 20 people in Chicago and was afraid we wouldn’t be able to find a boat big enough to hold all of us. Big Boat to the rescue! Our communication with the staff beforehand was friendly and helpful, even though we had to postpone the event a whole year due to COVID, and on the day of the event, our captains Mary & Patrick were very helpful and accommodating to our group. We had a blast riding out to the “Play Pen” and anchoring for drinks and a swim. Highly recommend!

Captain Linnea and her first mate Hailey made our trip perfect! They took us out at sunset and made sure our trip (and surprise engagement!) went smoothly. They put safety first but also allowed us to have the most wonderful time! 10/10 recommend! It was a beautiful and perfect day, thanks to them!

Booked a night cruise on a powerboat for my birthday, was an amazing experience. Captain Bill and his assistant Tatiana were great people, and accommodate all our needs during the charter. The route taken was beautiful and I couldnt have asked for a better way to spend my birthday. Book through them!

A perfect way to celebrate my partners birthday. Captain Rob was amazing. He was very flexible with our needs, laid back, safe, and he made sure we had a fun time. I would highly recommend Rob and Chicago Sailboat Charter to anyone looking for a good time. 10/10

We had a boat rented for a buddies birthday. Everything was a go until about 30 minutes before we arrived. Received a call to let us know that our reservation was cancelled due to some engine malfunction. Our group was from out of town and any notice would have been better rather than 30 minutes before our trip. When we were notified unexpectedly, they were a pain to deal with when getting a refund. Waste of time and terrible customer service. They do not care about the people that invest money into their business and are selfish when regarding to the satisfaction of their customers. Very disappointed in this company. I would refer you to any other charter rental service other than this one.

Beautiful sunset sailing!

Really bad boat service cancelled our charter 30 minutes before the sail and didn’t even try to give us anything to make up for it. Don’t waste your money

Highly recommend going through Chicago Sailboat Charters for their semi-private sails. They provided clear instructions on how to get to their dock, our captain, Dennis, was professional and made sure we had a great time and the ship was well-maintained and perfect for eating, drinking, and enjoying the great views. Cant wait to book another sail!

Great boat service

Updated review as of 9/30: the company contacted me after my original review below. They offered to extend my voucher to include a sail in late September when I could actually fly out to use it. I am editing my star rating from 2 to 4 for two reasons:1) they did reach out to respond and accommodate me. Whether they did it on their own or as a result of my review here is unknown.2) I REALLY had a great time sailing with the skipper who actually took us out and want the rating to reflect what a great experience it was despite the scheduling difficulties and rudeness of the staff replying to customer service emails. Ken was a fabulous captain and he will make sure you have a good time whatever that looks like for you. For me it was getting to helm the boat once we got out of the harbor! The other passengers on our sail didnt really care to steer or learn how to sail (which is also totally ok!) But they had a great time picnicking and drinking and catching up. Everyone had an excellent time and Ken made sure everyone was comfortable. I really enjoyed my conversation with Ken about his sailing experience and the weather patterns on lake Michigan. It turned out to be a really fun experience thanks to him and Im glad I got the chance to revise my review. If you can get past the scheduling snafus you will likely have a fabulous time sailing with experienced skippers.Original review:I bought a voucher through Groupon last year and was really looking forward to this sail. They cancelled due to weather (completely understandable!) and gave me an extension.problem was: 1) I live in Portland Oregon and 2) COVID hit. So I couldnt use it before it expired.I emailed the company to see if they could extend again and they replied back in July saying they could give it until 9/15. I went to start booking my trip including flights. Then discovered that they only had sails listed in August and beginning of September. I work at a hospital and my schedule is published 2 months in advance and were especially tight now due to covid. I couldnt make the one date in September that they had available, so I wrote back again asking for help. Keep in mind Ive already paid for this voucher last August 2019!So far theyve been super unhelpful and uncaring. I was told I could pay another fee to extend my voucher again, and also told they dont have any other dates they can accommodate me this season. So I should just pay the extension free and HOPE they honor it later and have dates I can sail with them?? No thanks. I was super put off by how short and curt the emails are. They dont care about their customers in the least, no matter if youre from Chicago or across the country, or an essential hospital worker trying to catch a much needed break, nothing. Too bad

We had a wonderful Labor Day weekend cruise with Captain Rob! I brought my parents in and we had so much fun with this crew. I would highly recommend taking friends and family!! Thank you so much again Rob you made it a blast on the water 😀PS this company is great at answering any questions you have before your trip and are very responsive. This made planning very easy!

Chicago Sailboat Charters is simply fantastic. Ive been using them for years both for personal outings with friends and also for company events. Marty and his crew are very professional and fun to hang out with. They go above and beyond to make your sail a blast and are very accommodating. During the last sail, we wanted to go down to Oak Street harbor instead of the water towers. They took us down there, dropped anchor and we had a great swim. Very reasonably priced and they run deals often. Highly recommended.

We took a group of 10 out with Captain Rob and First Mate Allison and the service and experience were phenomenal. We had two families with kids ranging from 12 to 21 and everyone had a great time. We did a fireworks charter on Wednesday evening off Navy Pier and the views were fantastic. Safety was paramount with the kids and the crew did a great job making this a really enjoyable experience.Thanks Captain Rob!!! We will be back and request you every time.

We took the fireworks cruise on Saturday the 18th with Captain Steve and it was AWESOME! Everyone, from booking to sailing, was great to work with. Our mini-Family Reunion would not have been the same if we had not included this charter event! THANK YOU for everything Captain Steve [we feel he is now part of the family! He is such an AMAZING Captain]! The fireworks are just so much better from the vantage point of a boat! I recommend Chicago Sailboat Charters to anyone who wants the boating experience without all of the work!!!!!

Unprofessional, unethical and rude company. Doesn’t deserve 5 stars.

Never done a Sailboat charter thing before...to be honest it sounded too pricey and kind of a waste. Was referred to Chicago Sailboat Charters by a friend. Remarkably good time. Very friendly knowledgeable staff. Very Affordable. All in all a fantastic experience, would definitely recommend.

We had a wonderful experience with Capt Gregg Pavalon. Despite it was in May, the weather was very cold. We were very well advised to change our plan and to enjoy the river instead of just staying on the lake. The speed boat is very comfortable, Capt Gregg was great, friendly and easy going, he let us sit in front to enjoy the beautiful view. We really enjoyed the 3.5 hours we had on board and will remember forever the special evening of the graduation of our daughter. Thanks a lot!

Anytime you combine sailing and drinks, you know you are heading for a good time. And Chicago Sailboat Charters did nothing to disappoint. Everyone from Marty to our Captain Matt and his right hand man Rick were great. Even with some turbulent waters, they made everyone in the boat feel extremely comfortable and answered every question we asked.We were out on the water for roughly over a hour but the time seemed like it was flying by because we had so much fun. Matt and Rick had control of everything the whole time. Matt shared his stories of past groups and their wild times and Rick took care of anything we needed.To live in Chicago and not go sailing is almost a travesty. So you decide to charter out a sailboat group, make Chicago Sailboat Charters your first stop. These guys are professional, fun and knowledgeable and go above and beyond to make you feel comfortable.

Awesome time. Chip was an out of this world crew member. He let me just sail the boat the way I can wanted based on my experience. It was a blast. Definitely worth every penny. ..Although it was a lit less expensive than the other charters available. Would recommend highly! !!!

We chartered a powerboat for the fireworks cruise and hands down this was worth every penny. It was a pleasure dealing Chicago Sailboat Charters. Highly recommend. Captain Greg and Juan Pablo are awesome.

Great time sailing and drinking. Their service is outstanding

The real way to see the Chicago skyline is by boat. Our group rented a 40 power boat from Chicago Sailboat Charter and had a wonderful time. The staff was courteous, attentive and fun! We will rent again.Robin SJ

We just went out sailing with this company June 11, 2016 Saturday and Captain Stephen is who we had taking us around. It was a blast, it was for my husbands birthday and our adult children and their spouse / girlfriend went too , we all had a great time. Very professional, and very knowledgable Captain he had lots of great information and even let me, our son and my husband do a little driving, it was fantastic my husband really loved it. The boat was very clean and organized. Highly recommend Chicago Sailboat Charter and Captain Stephen - thanks for a wonderful adventure! The Burgette Family

A great time was had by all. We look forward to our next adventure.Thanks Chicago Sailboat Charters!