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    Come Sailing

    4.6 (10 reviews)
    Closed 9:30 am - 9:00 pm

    Services - Come Sailing

    Boat charters

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    Fun day sail with Captain Mike! We can't wait to go again!
    Colleen L.

    Captain Mike took us out mid day and we have a beautiful day for sailing. He was so accommodating to us. He was there but you barely knew it. The boat was clean & he had refrigerator space and ice for us. We packed like we were going to two days, not two hours, and the boat didn't seem crowded. We had so much fun and can't wait to go out again! Thank you Come Sailing! Also - an added bonus is that if you park in the Millennium Park Lakeside garage before 10 am the price is only $16! What a deal & super close & convenient to the boat.

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    10 years ago

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    Michael B.

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    9 years ago

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    Michael B.

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    10 years ago

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    Review Highlights - Come Sailing

    Captain Mike is a kick - very chill and fun and obviously loving every minute of his awesome life.

    Mentioned in 8 reviews

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    The Salty Dog Sailing Co. - Picture perfect sunset!

    The Salty Dog Sailing Co.

    (24 reviews)

    Near Southside

    Captain Kirk Kessler, a United States Coast Guard - Certified Master Captain, goes all out to give…read morehis passengers a wonderful experience. His boat, the Peony, is equipped in a manner to meet the needs of his guests. His first mate, Woody, a chipper mini Golden Doodle, adds a fun touch to each outing. Kirk is extremely professional, going over his shipboard rules with all his charges before they embark. His rule #1 - "Stay on the boat!" Captain Kirk gets a sense of each of his sets of guests, and how comfortable (or apprehensive) they are on the water. Passengers preferring a sedate, "gentle" excursion will get one (to the extent weather and lake conditions permit); those guests up for a more adventurous outing with 15-30 degrees of heeling will have their wishes fulfilled. As a USCG-certified Master Captain, Kirk knows what he needs to do to trim the sails and change his headings to make his cruises pleasant ones for his passengers and their predilections. A charming host/skipper, Captain Kirk will make your sail/cruise an unforgettable one - withe the beautiful Chicago skyline as your sunset backdrop. You can't do better than Salty Dog Sailing Co.!

    I highly recommend chartering with Salty Dog. Captain Kirk () was very professional. I was a…read morelittle nervous, but he set everyone in our party at ease. The boat comfortably fits 4 people, and you can just sit back and relax. Woody is extremely friendly, greeting us on the dock when we arrive, and sleeping next to us the entire trip, except when we turned and he had to flip to the other side! And it's true sailing, we went about 3.5 miles from shore, getting some incredible views of the city. It was a great day, great conversation and an overall awesome time!

    1st Class Charters Chicago

    1st Class Charters Chicago

    (8 reviews)

    Douglas, Bronzeville

    My friends and I have chartered a few boats here in Chicago, but this was by far the best…read moreexperience we have had. We actually had to reschedule our initial cruise last minute due to bad weather. The boat owner, Russel, was very communicative and made the best of the not-so-great situation. He graciously offered to allow for our group to enjoy the boat for a lesser amount of time and stay at the dock. We were also able to reschedule for the following week and go out with Captain Brian at that time. Our group had such an amazing time during both sessions. We certainly had some strong personalities in the bunch (myself included) and Captain Brian was such a great sport. He was very professional but also blended in so well with our group that he was like another guest. We will without a doubt be reaching out to Russel & Captain Brian again for future events. Thank you both for making this such an unforgettable experience for us and our guests.

    As boating season starts in Chicago, I just wanted to let you know that Russell took me, my…read morechildren and their significant others out for my "birthday celebration" and it was thee BEST boating experience this Chicago gal has ever had. Russell took us on the most beautiful route and his boat is beautiful and comfortable for viewing, eating, drinking and laying out if you like. My favorite moment was when we anchored and me and my kiddos did a celebratory jump into the lake as Russell videotaped us. Big Thanks to Russell for the BEST Boating experience in CHI. He is so knowledgable and experienced that I highly recommend 1st Class Charters Chicago!!

    BBQ Pontoon

    BBQ Pontoon

    (51 reviews)

    Chinatown

    What a dope experience! My SIL has lived in Chicago for awhile and we went to visit her! She said…read morewe HAD to do this experience because it was so fun. Eating pizza, driving yourself on the boat and site seeing with friends! What more could you want? We rented the boat, it was for 2 hours and they provide 1 frozen pizza for 10 people. I wish it was more.. considering you're paying about $60 bucks per person (taxes, gratuity). Since she's done this before, we bought 3 more pizzas and snacks before we arrived. So cool and since we did it in the evening, it felt so great and was gorgeous. The moon was full, and it was an awesome evening. Getting there/parking was great. They have a huge parking lot. The employees were kind, walked us through the safety and let us on our way. It was an awesome experience, check it out but keep it quiet!

    TL;DR: Christina and Rich were awesome and informative, clean boat and easy to operate, grill on…read morethe boat was tricky but it cooked the pizza and the pizza was good, 10/10 would recommend! This was an amazing and much needed experience, especially right now. My friends and I arrived a bit too early, but we didn't have to wait long because Christina was able to check us in and get us on a boat in no time! She was really nice and gave us a quick overview of what to expect before we headed down to the dock. They are limiting it to four people/per boat right now, but honestly that was perfect because we had room to spread out a bit. The boats are sanitized after each group too. Rich thoroughly explained how to operate the boat and our route options. None of us had ever driven a boat before, and he helped us feel comfortable with it before we left the dock. I was one of the drivers (we took turns) and I though it was a lot of fun actually. Also, they have pizza that you grill on the boat and it's pretty good! The grill itself was a bit tricky, but the pizza got cooked, so that's all that really matters haha. 10/10 would recommend!

    Come Sailing - boating - Updated May 2026

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