SO MUCH FUN!! How it works: You charter a boat along with the captain and crew. The boats are owned by the company. We chartered a boat on Labor Day, with Bill and Nancy. We departed from Montrose Beach. We were able to bring our own drinks and snacks for the sail. There were 7 of us total at ~$100/person. We specifically selected this company because they had a money back guarantee in the event of inclement weather - most other boating companies do not offer this! HUGE PLUS. Fun Fact: All of their boats mean "Lost" in different language, but not to be confused with lost at sea! read more

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. read more

Chicago Sailboat Charters - Boating Near Me - Chicago, Illinois

Captain Rob and Jill were great. Everything ran like clockwork and they were accommodating on the boat. Great conversationalists as well. I appreciated the simplicity of booking and acquiring their services. It felt a little too easy to be true but it was. They just have an efficient and fun operation. Thanks captain Rob and Jill! read more

The best boating experience ever!!! After doing a ton of research, I came upon Chicago Sailboat Charters. I found them through their amazing reviews and recommendations. They were quick to respond and answered all of my questions. I ending up booking a Cruiser Class Power Boat for a bachelorette party of 11 girls. After booking, you receive a list of captains to choose from and I chose Gregg after reading countless, 5-star reviews! When it comes to your choice of captains, you need to choose Gregg!! I cannot rant and rave enough about how accommodating Gregg and Lori were. They went above and beyond for our boating excursion. And Lori captured the entire trip with 200+ photos! As if the day couldn't get better, Capt. Gregg and Lori took us up the Chicago River and accommodated our group for an extra hour. Everyone in our bachelorette party agreed that the boating day was by-far, the best part of the trip!! I highly recommend this company. read more

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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! read more

Chicago Sailboat Charters - Chicago skyline / sailboat cruise. - Boating Near Me - Chicago, Illinois

Had the best time with Bill on the water. Very knowledgeable about the parameters and specs of the lake and overall vicinity. Laid back and very personable. Would definitely do again and next time bring some friends. The only recommendation would be to set up a Venmo account for tips. Worth every penny! Thanks Bill! read more

Chicago Sailboat Charters - Boating Near Me - Chicago, Illinois

The seven of us had a tremendous family outing with Captain Gregg on a beautiful, clean, well-appointed 40-ft powerboat rental from Chicago Sailboat Charters. It was a perfect day cruising up the lakefront, listening to our music, swimming off the back of the boat in "the playpen" traveling through the locks into the river and back again. Captain Gregg couldn't have been a more courteous host for the day. Truly, a wonderful staycation trip for us during the summer of COVID. read more

Chicago Sailboat Charters - View of the Chicago skyline - Boating Near Me - Chicago, Illinois

What an amazing time! We sailed the beautiful Lake Michigan early one Friday morning in August with a great crew. We did the semi-private boat sail and it was wonderful. The captain Greg kept the conversation smooth and easy and it made for a great start to a wonderful weekend. read more

My friends and I had the best time on our charter and Captain Gregg and Amanda were amazing. They took such great care of all of us and were super fun and professional. This was a surprise for my husband's birthday and it could not have been better. They both made sure all day we had everything we needed to make it a great day. Chicago Sailboat Charters were super responsive and answered all if my questions before we arrived. They made sure my friends and I had all of the details of where to be and when. I will definitely be making this an annual thing. Thanks again. read more

Chicago Sailboat Charters - Boating Near Me - Chicago, Illinois

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Captain Rob was great! He went over all the sailing precautions along with the additional COVID safety rules. Once we began sailing, everything was a breeze. No problems and a great time. Would recommend to anyone! read more

Our group of 7 chartered a 40 ft powerboat to see the Chicago Air Show and all I can say is WOW! Absolutely the best way to view the show, still in awe over the RAF Red Arrows and the Blue Angels, seeing their amazing maneuvers against the Chicago skyline was truly breathtaking (and heart stopping at moments)! Captain Bill and Ava were lovely. They are knowledgeable, genuinely kind and helpful, they were clearly vested in making sure we had a great time. They helped with food, drink, even taking photos. They found us a great spot to watch the show and also for a dip in the lake, they had life jackets and noodles so you could relax and enjoy the waves. The boat is perfect, has a large galley with tons of fridge space and they had large coolers with ice. They also had plastic cups, plates, napkins and bottled water. Overall not a single detail was missed and we all had the best time. We are definitely doing this again next year. Thanks for a wonderful day! read more

Amazing time! Our first time renting and Captain Gregg and Steve didn't disappoint, they were amazing. They gave us a tour of the lake and the river. Captain Gregg did an amazing job navigating and we never felt uncomfortable at any time. His partner Steve was an amazing host as well. I highly recommend Chicago Sailboat Charter and don't forget to ask for Captain Gregg and Steve. read more

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Where do I start?! Captain Gregg was very communicative starting with his rapid response for my request to engage him as our captain. He followed up ahead of our boat date with all the details and on the day of. He was super prepared with all the necessities and went out of his way to make sure we truly enjoyed our boat ride! My friends and I can't wait to cruise with him again! Thanks Capt. Gregg! read more

We had an awesome time for my bachelorette party sail over Labor Day weekend! We had Capt. Gregg and he was amazing! I literally had no complaints! He was so much fun and made sure we all had a great time!!! I recommend this company and Capt. Gregg!! read more

Chicago Sailboat Charters - Boating Near Me - Chicago, Illinois

Capitan Conway and Tatiana were so much fun! They had great personalities for this type of work - east going, safe, and knew how to read a crowd. Captain Conway joked with us, pointed out things along the shoreline and water, and made sure we all were safe and comfortable. Tatiana was so gracious - always offering to grab us drink refills and anything we needed below deck. They truly took care of us the whole time. The water was bumpy as it was a busy weekend (air and water show) but they instructed those who were motion sick how to reduce their symptoms as much as possible. And of course, they offered us out-of-towners much needed pizza advice - which we ended up using and loving that night for dinner. The ride was peaceful and unique, something I couldn't have done anywhere else. I would highly recommend! Tip: definitely bring a plethora of food and drink. The more you bring the more fun! No red wine though :/ read more

Chicago Sailboat Charters - Sailing for Corey's bachelorette party - Boating Near Me - Chicago, Illinois

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! read more

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Ahhhh-mazing experience. First off, Captain Matt was extremely professional providing all guests with an enjoyable and memorable ride along the gorgeous coast of Chicago! Matt was super laid back and his love for sailing was infectious only rivled by his knowledge of the city & sailing! We climbed all over the boat - Verloren - which was a gorgeous sailboat; captured the views of the city from every angle. I'm not sure which was more breathtaking - the sunset views over Chicago or the lit up city lights as we sailed back into Belmont Harbor?! By the end of the evening, we were convinced we should throw caution to the wind and buy a sailboat....or another ride on a Chicago Sailboat Charter :) I should add we purchased our ride on Living Social and had absolutely NO issues utilizing the credit (which is the case with some vendors) - overall fantastic experience. We'll be back - thanks Matt!!! read more

Chicago Sailboat Charters - View from Verloren sunset sail boat ride! - Boating Near Me - Chicago, Illinois

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Captain Gregg was simply wonderful! I came into town from Florida to visit a friend for the weekend and have been on many boat rides, but this was probably one of the best experiences I've ever had. Gregg was extremely accommodating to our group of 9 and even had ice, cups, a cooler and speaker for us to play music to enjoy our Saturday morning 2 hour ride. Looking forward to booking again when I come back in August!!!! read more

Okay, I got really sun burnt on this boat but that doesn't hinder my review at all. We schedule a 3 hour sailing trip around the lake as part of our bachelor party and would do it again in a heart beat. We met our captain outside of our gate and was blown away with what was about to happen within minutes of being on the boat (no pun intended). Our captain was awesome and was concerned about our safety at all times, especially with us drinking on there, so he made sure to tell us how to go about navigating the boat safely (three points of contact rule). It is BYOB, so make sure if that's your thing that you bring plenty of supplies to last the full three hours, they provide cups, ice, water, and the boat. AND (drum roll please...) A party captain! Matt, our party captain, was there to refill our drinks, get us water, sunscreen, ANYTHING from below the deck- talk about relaxation. I was not expecting this at all and was blown away with how friendly they were with us, for I'm sure they've had some pretty outrageous experiences on a sailboat. If you are looking for a fun family gathering or boat to start your Bachelor Party off right, look no further! Would recommend Chicago Sailboat Charters in a heartbeat. read more

Chicago Sailboat Charters - View of the city from the lake - Boating Near Me - Chicago, Illinois

Scored a Groupon for a semi-group sail. Loved it! Great customer service, both from the office and Captain Steve. We're looking forward to our next sail already, well worth it with or without Groupon. We did an Tues evening sail on the Verloren, a tip-top boat which was really roomy for the six passengers and the Captain. (Wed & Sat fireworks already booked up for the month.) I'm motion sick, so I swallowed some pills, and crossed my fingers. No worries - It was so calm out there, Steve had to use the motor. I even polished off a half bottle of wine, which was all we'd brought besides dessert (motion sick worries), but another couple had brought along a big picnic spread and shared with all of us, which was nice, and we shared our desserts. Beautiful sunset, wonderful skyline especially at night, Hubby (the amateur sailor) was happy to have someone else do all the work. We had such a blast, and left the boat so happy. read more

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I bought a Groupon and upgraded tickets on their website as an anniversary surprise for the boy. Weather was absolutely lovely. Perfect for sailing! There were two other couples on the boat. The ride out to/into the lake was very enjoyable. However, I began to get nauseous. I wasn't the only one because other passengers began to feel the same way. I didn't want to make a fuss and ruin everyone's fun, so I held onto the boy, remained quiet and closed my eyes for the rest of the trip back. If you think you get motion sickness easily, don't make my mistake and go downstairs into the boat. It was like a grown up version of a bounce house. Oy. But if you don't get sick easily, go on ahead with your bad self! Unload any snacks or drinks you may have since the boat is BYOB. Overall, the trip was very enjoyable! Absolutely loved seeing the Chicago skyline. Captain was nice and seemed very knowledgeable. I would just suggest perhaps instead of racing to see how far you can get within an hour and a half, float along the lakefront and enjoy being on the lake? A la "it's not the destination, it's the journey" kind of feel? read more

Highlife tallboys...check, Jewel brand chex mix...check, legit boat shoes I get to bust out once a year...check, hoodie because it's never going to get warm in Chicago and before we know it it's going to be winter again...check. Set sail with Chicago Sailboat Charters last night, and I have to say, it was a great way to spend a Monday night. We got on board one of their luxury 39' sailboats for a 6pm skyline cruise of Lake Michigan. The boat had all the amenities you could ask for. Below deck, there were 2 bedrooms, a small dining area, and a kitchen which featured an ice bin for bottle storage, fridge, cups, coozies, wine openers...basically whatever you needed. Also important for those who are drinking, a bathroom. We had the priviledge of having Captain Steve as our guide. Honestly, I would probably book another boat tour just to hear more of this dude's stories. Born in France, moved to Chicago at an early age and took up sailing with his dad, lived in Mexico and owned a parasailing company, plays in a blues band, owns an Escalade limo, and is an ordained minister if you want to get married on the open waters. Forget the Dos Equis guy... The sail was a great time, and we had some amazing views of the city. I would definitely use this company if you are looking to book a sailboat in Lake Michigan. Everyone there seems very professional and most importantly, flexible, given how weather conditions can change rapidly in Chicago. Also gotta give a shout out to Alison, Captain Steve's assistant, who was doing work up top managing the sails! read more

Chicago Sailboat Charters - Boating Near Me - Chicago, Illinois

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Ahhh Captain Rob, A majestic and seasoned sailor. Seriously though, we had a fabulous time. The water was a little choppy but we got lucky with a beautiful evening cruise. We're a fun group, but Captain Rob really set the whole trip off. It means a lot to have an entertaining, well spoken and passionate party leader. He was all class and seriousness when it came to safety but he made sure we all had maximum fun and a pleasant trip. 10/10 would sail again. read more

Chicago Sailboat Charters - Majestic - Boating Near Me - Chicago, Illinois

We went out on a charter with Captain Gregg...he was awesome! Our view of the city was amazing and the chance to enjoy the water was great. Captain Gregg did not disappoint at all. The boat could have been a bit cleaner but it did not take away from the morning on the lake. read more

Captain Rick! Captain Rick! A couple girlfriends and I chartered a small sailboat with Chicago Sailboat Charters for a 30th birthday. The booking process was super simple. On their website I was able to see which boats they had available on the dates I wanted, and after entering my contact and credit card info, we were booked! Simple as that. A small sailboat charter (room for 5 passengers not including the captain) for 4 hours cost $640 plus tax and tip. Captain Rick got in touch with us the morning of our charter to make sure we knew how to get to the dock. After boarding the boat and telling him we just want to head straight to the Play Pen, we were on our way. Captain Rick is super fun. He cruised the Play Pen for us so we could find the perfect spot, helped us put on music, and just be loud and crazy. We brought our own booze on board and he had ice and waters waiting for us. I would definitely rent from Chicago Sailboat Charters next time I'm in Chicago, and ask for Captain Rick, of course! read more

Chicago Sailboat Charters - Captain Rick is the best! - Boating Near Me - Chicago, Illinois

We had a fantastic sunset cruise! Booked with a Travelzoo discount so we got incredible value. Boat was in great condition and we had a fantastic captain with tons of experience. The views you can get at sunset are incredible and would be equally enjoyable for a local like myself or someone visiting from out of town. You can BYOB as well as bring food on board which was perfect for us. One nice thing about these tours is that they cap the groups at around 6 people which makes it much more relaxing and comfortable than larger tours. This would be perfect for a smaller group of friends or for couples who don't mind getting paired up with another group(s). read more

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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! read more

Chicago Sailboat Charters - Girlfriends Sunday Funday - Boating Near Me - Chicago, Illinois

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Chicago Sailboat Charters rocks, and if you get Captain Steve and Alison you are sure to have an awesome time. He is very knowledgeable, friendly and personable, they made it feel as if you were just out for a ride with friends as opposed to being on a charter line. He made you forget all about the 3 foot waves and wind, and we had nothing but confidence in his skills in dealing with these conditions. I can honestly say this has been my best and favorite sailboat experience so far, and I've had quite a few. I will definitely be back to Chicago Sailboat Charters, and I will definitely request Captain Steve and Alison! read more

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Thank you Capt Larry and Amy for a beautiful boat outing on Lake Michigan. They were so accommodating and incredibly friendly. We had many options for our a.m. Sunday funday...I am only able to remember two. The first being a river tour and the second (we chose this option) was the playpen where we anchored the boat not far from Navy Pier. Swimming, laughter and great conversation...what a treat to relax and spend time with cool people. read more

Chicago Sailboat Charters - Beautiful Sunday on Lake Michigan! - Boating Near Me - Chicago, Illinois

One star is a huge stretch. If zero was an option, I would give negative zero. A group of my friends and I scheduled a 3 hour, 45 minute boat ride for today. From the beginning the captain Robert was not warm and welcoming. From the beginning, he was very discriminatory towards me and my friends. He went over the rules of the boat and started the trip. I dozed off a couple of times in which he assumed I was drunk and passed out. I tried to explain to him that I was fine and we should continue the trip. He then said he did not want to continue with the trip and was very rude. He turned the boat around and took us back to the dock within 10 minutes. He was absolutely condescending and snobby although we were all sitting down on the boat. I will NEVER use this company again. Robert ruined my first experience in Chicago. I have been on many boats in different countries and this was the first time I had ever felt discriminated on. I will ensure that my friends and family avoid using services of this company as long as they have racist, discriminating captains like Robert. I know beyond a shadow of a doubt, that if this was a group of white clients, this would not happen. read more

We did a sailboat charter with them. Captain Will was incredible. He knew what he was doing, was incredibly friendly, and we met great people on the ship. I think this will become a monthly outing for us! I highly recommend this for anyone looking for a good date night excursion! Thank you! Bryan and Fiona read more

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Hosted a team of Executives on Chicago sailboat charters largest 39' sailboat. We had an excellent 3 hour sailing outing that went well out into the lake and provided an excellent view of Chicago's city lights. Captain Stephan, in addition to being an extremely competent Captain, was engaging and provided great conversation that enhanced our overall experience. The boat was immaculate and in perfect condition providing our executive team with a top notch venue. Captain Stephan was aided by one crew member who served drinks and food and generally helped us around the boat wherever we needed assistance. Overall a 5 star rating is well deserved. We are already planning our next outing with chicago sailboat charters. Highly recommended! read more

Chicago Sailboat Charters - Chicago city lights from our sailboat - Boating Near Me - Chicago, Illinois

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I recently booked a sail for a group of girlfriends during a bachelorette party. From initially inquiring about our chartered sail on through the actual sail, our experience was top notch. Responses from the company to questions were fast and informative. They were also organized and very detailed with information leading up to the sail and directions to the meeting point. When we arrived, we were greeted by Captain Conway and Alison. Those two were fabulous! We felt safe, and we also had a GREAT time. I can't say enough about how much fun we had and what outstanding hosts Captain Conway and Alison were. Thank you! read more

Captain Gregg was phenomenal! He was attentive to all of my guests needs and communicated with me the whole trip about what to expect. He gave us a great day and I would definitely book with him again in a heartbeat! read more

I purchased the $89 voucher for two seats on a semi-private sail for my boyfriend's birthday, and we had an amazing time! Captain Ken was great and very knowledgeable. The experience was absolutely worth the price and the views of the city from the sunset cruise were phenomenal! I would recommend this experience to anyone. read more

Had a great time on the boat with Capt. Gregg and first mate Steve. They were super welcoming and helpful with my group. The weather was a little chilly/windy for a 7/6 boat tour but they made the best of it! We still got to jump in the water and play around! Will definitely do another boat tour! read more

Captain Gregg and First Mate Liz were terrific, laidback, go with the flow and appropriately proactive in anticipating and taking care of our needs. They arranged for catering as well, and it was great. We spent 3 hours along the waterfront and up and down the river. Never a hitch, never a worry; always very polite and professional. We'll be back! read more

Chicago Sailboat Charters was great from start to finish! Had a wonderful day out on the lake and they made it super easy. We had Captains Gregg and Liz - they were super fun, professional, and made our sail fantastic! We'll definitely be back out wifh then soon! read more

Ok I literally cannot believe they have a perfect rating. We booked the sail trip 1300$ for 13 of us for 3 hours. It's all byOB, I think for 1300 they should provide at least 2 bottles of wine. We were coming from about an hour and a half away and the weather forecast was horrible so I Called the day before and talked to Pj. He specifically told me he would call me at 12:30 (3 hours before our sail) to let us know if we needed to reschedule or not. Great. My friend was getting a different story so I Called again and got Marty, the owner, I told him what Pj told me and Marty basically called me a liar and told me Pj would never tell anyone that. Then we got on the boat. It barely fit us and we were uncomfortable. The captain Steve had about as much of a personality as my left shoe does. Bad experience. Never ever again. read more

Chicago Sailboat Charters - Boating Near Me - Chicago, Illinois

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Beer + sun + friends + Cap'n Steve + First Mate Lauren = great time. Highly recommend it for team outings. Especially if someone else is picking up the tab (thanks, Google). read more

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