My wife and I sailed with Captain Steve last month on LOST and had a great night sail. We enjoyed it so much, we got a group of friends together and made a reservation to sail on one of their bigger ships next year. Overall, great service from start to finish, clean boat, nice captain, a great experience. read more

Excellent! Fantastic! Wonderful! Professional! I did have a scheduling problem (note, I use a Mac, so it may have been the platform) We called and received immediate attention and were immediately upgraded. I would highly recommend Chicago Sailboat Charters! read more

Amazing!! Beautiful boat! Amazing professional but fun crew to work with! captain Steve was amazing very protective of all of us and professional also soooo much fun! 1st mate Peter was amazing also he took over all of our stuff organized and served us like queen and kings! They both pleased us with everything. It couldn't be a more perfect day. I will recommend everybody to have a day out in the water with captain Steve and Peter . Also Marty is amazing person very pleasant to do business with and very sweet man! I will do this 100 times more... thank you captain Steve, Peter and Marty for making this adventure the most spectacular birthday and promotion celebration ever!!! Worth every cent time and energy read more

Chicago Sailboat Charters - Amazing boat! - Boating Near Me - Chicago, Illinois

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Highly recommend this company. Rented a boat for a friends birthday party and had an amazing time. Captain Larry and 1st Mate Tom were awesome! The combination of the great crew and amazing weather we had this Saturday made the party a huge success. I'd definitely rent again! Tip:Parking can be a challenge so be sure to arrive a little early. The lot closest to the dock was full so we had to unload the food and drinks and park at the Millennium Garages a couple blocks away. read more

I was celebrating a bachelorette party this past weekend, and I could not have asked for a better experience with Chicago Sailboat Charters. Captain Rob was an absolute delight. He laid down some clear and reasonable rules, helped get the girls some drinks when the boat got a little rocky, and he chipped in with some great one liners too. I didn't organize the party for the bride, and I had no idea what it meant to sail the harbor in Chicago, I can only hope that all boat rides are like this one. Thanks for a great afternoon Rob! Cat read more

If i could give 0 stars i would. Booked a fireworks cruise for tonight. About 40 min before the crusie got text, not a call, that it was cancelled for "big waves". I have sailed for many years and marine forcast was 15 knots with 2-4 foot waves. Maybe they have new captin, but if captin can't sail in that I would be worried about your safety. This is basically flat seas. This really worries me and wanted everyone to know especially tourist and those that don't sail regularly as i am not sure what they can safely sail in then. read more

One of the highlights to our Chicago trip! Gregg and Lori were so accommodating and did everything they could to make our experience a memorable one. If you're thinking of chartering a boat in Chicago, go with Chicago Sailboat Tours! read more

We had a group of 9 girls out for a fun day on the lake. Captain Gregg and Liz were so awesome! The day started with some rain and storms--but Gregg and Liz made sure it was still a great time. They made sure we always had drinks and the music was blaring. It was such a fun day and we will def use them again!!! read more

Two years ago I got a Groupon and had a great experience with Chicago Sailboat Charters seeing Chicago from the lake. That was my first time sailing, and if you've never seen the skyline from Lake Michigan, you're missing one of the best views of our city. I enjoyed it so much I bought a full private charter last year when I had family in town. We had Captain Marty for the private charter, and he was knowledgeable and professional, and also a great host and fun to be around. Since these sails were so much fun, I decided to make it an annual tradition and I purchased a "semi-private" sail as part of their "winter special". Unfortunately, I ran out of time and was not able to use it this summer. However, (thankfully) CSC agreed to honor my purchase and has allowed me to book a sail for next spring. In conclusion, the sails on Lake Michigan have been great, and CSC has been an outstanding company to work with. I'm looking forward to my sail next spring! read more

Our group was a bachelorette party of 8, and we had Captains Gregg and Liz. They were so awesome and made our charter absolutely perfect! Captain Gregg was easy to communicate with leading up to the charter, and made sure we knew exactly where to go. Captain Liz was taking photos of our group and helping us with drinks and music. Both made sure we were all safe and having fun. I would definitely recommend this company to anyone looking for a unique and fun way to see Chicago! HIGHLY suggest you cruise down the downtown river- best way to see the city. The views from Lake Michigan can't be beat, either! read more

For my birthday, my friends took me out for a chartered boat cruise with this dude Matt as our Captain. The boat was awesome. I think it was 39 ft? It was Saturday morning of Memorial Day Weekend and all was calm on the water and a little cool but I we all loved the three hours on the water. Matt was very informational and so professional. We loved his stories. A humble guy who just made the cruise very fun. I will use this Charter service again. J-D read more

Just finished a birthday cruise for my friend. Captain Rob and Jill were amazing! Super friendly, incredibly accommodating, but completely professional. They were a lot of fun to hang with; it was two extra friends on the boat! Definitely will book again, definitely will request Rob and Jill! Thanks for a great day, guys! read more

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. read more

We had a great time cruising the lakefront then anchoring and swimming at Ohio street beach "the playpen". Our Captain and crew were amazing ! I would definitely recommend this company. read more

Chicago Sailboat Charters - Boating Near Me - Chicago, Illinois

Overpriced for what you get. I've only done a similar sail in California and the standards aren't even parallel. I would NEVER book with this company again. read more

Our sailing adventure was an awesome experience. Captain Bill was a great guide and really made our experience enjoyable. Everything started exactly on time, and we had the flexibility to sail to different locationsaround the lake or go swimming. My husband was interested in learning all about the sail boat, and Captain Bill had all the answers. Perfect afternoon of relaxation with great views of the city. I would recommend this for couples even thought the boat could fit 6... we had the boat to ourselves and had the flexibility to do whatever we wanted. read more

What a great organization! We went out on lake Michigan for a few hours with Graham and he was fantastic - friendly, informative and so good about explaining things and making us feel comfortable. Worth every penny! read more

Had a great time on the water with Captain Rob! My family (5 people total) booked a Monday morning sail during a recent trip to Chicago which ended up being one of the highlights of the entire trip. The weather was picture perfect and the boat (one of the large class sailboats) was spacious and comfortable, with way more space than we needed. Captain Rob was really friendly and knowledgeable. We were even able to anchor in the playpen to go swimming with amazing city views in the background. read more

Chicago Sailboat Charters - Amazing time on the water! - Boating Near Me - Chicago, Illinois

I had no idea what this was when my BFF scheduled this for her birthday with our other four best friends. She said to bring a dish and what I wanted to drink. So wine, strawberry basil salad and a present of course! OMG. One of the best times! Captain Rob was amazing! He let us do girl time and only offered suggestions. By the end of the amazing smooth sailing night we were all fast friends. Very clean, well equipped sailboat and Captain Rob made it so enjoyable by offering scenic routes, playlists, etc. can't wait to go back! read more

They are so friendly and really strive to make your experience unique. It's byob, they offer cups and everything else you would need. They let people help out with cranking ropes, steering the sailboat, etc. They're very informative, very fun, yet very professional. I would definitely come back, 75 minutes went by way too fast! read more

Captain Rob is a true gent and wonderful host. The boat itself was great, and well stocked with all the essentials you would need to have a brilliant afternoon on the lake. Our group of six had a blast, and we will be back next summer. read more

I learned of Chicago Sailboat Charters through Groupon and couldn't have been more pleased with my experience. Marty made the process of reserving a sail extremely easy. Unfortunately, my original sail was canceled due to weather, but the captain reimbursed our $10 parking fee and was very apologetic. That was so classy and a real testament to their customer service. Marty worked with me to rebook a sail and was extremely flexible. I plan on doing future charters and would highly recommend Chicago Sailboat Charters to anyone. What a great experience! read more

Great trip! Captain Matt was awesome! Highly recommend!

Eight of us sailed on one of the 40' luxury sailboats with Captain Steve last Friday and had a blast. The whole experience was unforgettable. It was a perfect day out on the water and the Chicago skyline looked spectacular. The boat is gorgeous, and Captain Steve was fun and professional. I will definitely recommend Chicago Sailboat Charters to friends. It's a perfect way to spend a beautiful summer afternoon. read more

Went out last night with captain Rob! He was awesome! He was very professional and his fun-going nature made you even more enthusiastic about this great experience, not to mention he got us a great spot to watch the fireworks! read more

This was, by far, the nicest and most entertaining sail I've ever taken! Captain Rob was phenomenal....personable, funny, and a talented captain. Everyone on the boat enjoyed a beautiful and relaxing sunset cruise while laughing our booties off. We will definitely book another sail! read more

I was another Grouponer who got my first Chicago sailboat experience at a nice discount. Had an absolutely wonderful time - 2.5 hour sail with a beautiful sunset, headed down around Monroe harbor as the skyline lit up, and a leisurely sail back to Belmont Harbor. The company was great - we initially had to cancel our date the same day we booked it, which they graciously accomodated. The two captains were everything you'd want - friendly, easy-going, great stories when you wanted to talk, left you alone when you just wanted to enjoy the views. As someone who has frequent out of town guests come into Chicago, I would put this near the top of 'Must-do's' for entertaining any visitors, as well as for yourselves. Since you can bring aboard some food and all the non-red liquid you desire, even the non-Groupon prices are a good deal for the time/experience it delivers. read more

We rented the power boat last night for seven of my family members, including my 9 year old nephew and 12 year old niece. We had a spectacular time, including a 90 minute river tour (Captain Larry is his own architectural tour) and front row to the fireworks in Lake Michigan. Steve was a fantastic first mate. We're already talking about next year... read more

I reserved the mimosa Sun 9-1130 Power Boat with 12 friends and it was amazing. The best time we've had on the water in our beautiful city! Our Captain Larry was awesome, very informative and was fun to be around. The power boat has everything you can ask for, plates, cups, napkins, sink, mini-fridge and even a bathroom. The powerboat has more than enough room even with our party of 12. Some of our guests took a dip in the lake and others just sat around having a few drinks, looking at the skyline and enjoying a great time with friends. I absolutely recommend this company to anyone that's looking for a great time on the lake. I've dealt with some shady companies in the past (Rivercity boat rentals) but this company totally surpassed our expectations. Thanks so much, we'll be reserving another boat soon. read more

We did a 6-person charter w/ Captain Rob and had the BEST time. Not only were we blessed with fantastic weather but it was such a pleasant experience all around - we were welcome to bring & enjoy drinks, snacks, etc. and got under way and out into the harbor immediately! Pick a summer night, request Captain Rob, and have a great time!! read more

We weren't even off the boat and my friend and I were already planning our next trip. We booked two of us for a Monday sail on the 31' sailboat. It was $300 for 3 hours, very reasonable and worth every penny. Captain Rick was so friendly and flexible. We'll definitely request him again! Chicago summers are short so make this top priority on your bucket list! read more

I booked a chartered boat on a recent visit to Chicago. I wasn't sure what to expect. In the end, I have no regrets and definitely recommend having this experience. The weather was perfect and the boat and staff were great. Capt Gregg was amazing - he definitely was very professional and made us feel very safe but at the same time was really fun and engaging. I would definitely recommend using Capt Gregg. You'll absolutely have a great time. read more

Steve was our captain. Super laid back guy. I certainly was envious of his lifestyle. We were late for our reservation, but he kept us out on the lake for nearly 3 hours anyway. He also upgraded us to a bigger boat since it was available which was pretty nice. It was early in the season, so the lake was a bit cold even though it was hot on land. We didn't get to see the entire skyline which was disappointing, but you basically have to rely on the wind that day to take you south from Belmont. Overall, a great experience. read more

Capt.'s Gregg and Liz were phenomenal... they were great hosts, the boat was super nice, and they navigated perfectly to situate us for an amazing fireworks display. Additionally, Gregg looks a bit like a rotund Armande Assante which further increased his stock in my book. Would highly recommend! read more

Captain Greg and Jenna were amazing yesterday! They were so kind and generous. I would highly recommend them and I will definitely be back!

My wife and I went on a trip this weekend offered by LivingSocial and it was one of the best activities we've done in Chicago! We went on a semi-private tour (us and another couple). Nice boat, friendly captain, beautiful views. Highly recommended for a romantic trip or to show off the skyline to out of town guests! read more

A few weeks, some of my relatives were in town. They'd done all the normal touristy stuff, so I decided a sailboat tour might be something unique. Captain Steve was there right on time for a lunch time cruise. We brought our own lunch and beers and went out for a sail. The wind was a bit low that day, but we made the most of it and sailed pretty far out into the lake, ate lunch, talked to Steve (who was a very interesting guy) and overall had a great time. We even got a chance to quickly take a dip into the lake! Highly recommended for someone looking for something different to do in Chicago during the summer and get away from the hustle and bustle for a few hours. read more

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. read more

What a pleasant afternoon. My boyfriend and I sailed on the "Blue" with Captain Mike. When we were running late and frantically trying to find the dock to make our sail time, he and the other passengers were gracious enough to wait and disaster was averted. Mike was very charming and laid-back but professional and we felt quite relaxed with him at the wheel. The views of the city were of course spectacular (how couldn't they be in Chicago?) but being a resident, what I enjoyed most was learning about life out on the lake, which I know surprisingly little about despite living two blocks from it, which Mike was very knowledgeable about. The sail was BYOB and we got to relax while enjoying some wine and scotch. When we got off someone on the dock commented "You look relaxed!" and it was true! Slices of life like this really puts into perspective the doldrums of your office job. read more

Just returned from the 3-Hour Fireworks cruise with my father. Had a blast with Captain Larry who even let me steer! Be sure to show up on time by the picnic bench! BTW: Parking is only $5 after 6pm in the adjacent lot accessible from Recreation Drive / Irving Park Road. Plenty of cups, plates, plastic silverware & water bottles are available on board. Sandwiches, fruit/veggie salads, vino are all great snack ideas. Can't wait to use up the rest of our Unlimited Sailing Groupon! & can bring two extra guests for $99! read more