So fun! Highly recommend this company. They take the time to call you beforehand to make sure all…read moreyour questions are answered. My family and I got captain Larry and he was so kind and told us fun facts about buildings that we passed by. I will for sure be doing another boat tour with them!!

Excellent time on Lake Michigan. We had to reschedule our first appointment due to bad weather and…read morewere so happy we made it back to Chicago just for this trip. We got lucky to have good wind and had a true sailing experience. Captain Conway knew what he was doing and we always felt safe and in good hands. We would certainly recommend this charter to anyone looking for a sailing trip while in Chicago. We will be back!

Such an incredible experience! We booked a sunset sail over Labor Day weekend, and somehow my…read moresister, her boyfriend, and I ended up being the only three guests on a boat that can accommodate around 45 people. We honestly expected that they might cancel with such a small group, but they still took us out and gave us what essentially felt like a private sunset cruise. The entire evening was beautiful and felt incredibly special. The boat itself was fantastic--my sister's boyfriend especially loved the netted areas where you could lie back, relax, and enjoy the water and the views. Being able to spread out and enjoy the sunset with practically the entire boat to ourselves was unforgettable. I really appreciated that they honored the sailing despite having only three guests. They easily could have canceled, but instead they gave us an experience we'll remember for a long time. I would absolutely recommend them and would sail with them again!

Captain Mike was so great!…read more It rained all day but we still were really excited to do this sailboat tour. Our tour was scheduled from 7-9 and Mike checked in numerous times throughout the day to make sure we were feeling comfortable with the weather - he was more than happy to accommodate if not. He was personable, knowledge and made us feel super safe along the way. And the Chicago skyline was STUNNING! Would def recommend!

Captain Lynda is a gem of a human: professional and focused, compassionate and kind, and most of…read moreall, she makes sure everyone has a wonderful time. The Joy of Sailing provides a unique experience for women to learn and grow together, bonding friendships and developing self reliance. Lynda's curriculum is thorough and well structured. She offers a perfect blend of skills training and pleasure sails in a community setting of supportive ladies! The best way to spend the summer in Chicago!

Highly recommend for anyone who is looking for a way to unwind, relax and escape for a little bit…read more I did the "Anything Goes" sailing and it was just what I needed. Relaxing music, wind in my hair, beautiful views and good company with like minded women. Even got to sail for a little bit and take a dip in the lake. Vacation of the mind. Lynda was great and she offers two different experiences, pleasure sailing and skills training. Depending what experience you are looking for, Lynda has it covered! Can't recommend her enough. Definitely check out her website for more information on her different programs. Plus right now she is offering a code, "Mermaid" for 25% off, if you are unsure and need the extra push. You won't regret it!

One of the best things I did while visiting Chicago! I booked the 8:30 p.m. Tall Ship Windy sail,…read moreand it was worth every penny. We left around 8:30 to 8:45, and by the time the 9:00 p.m. fireworks started, we had a front row view from the water. It was absolutely incredible. The captain and crew were friendly, welcoming, and did an amazing job. The ship wasn't overcrowded, so there was plenty of room to walk around and take in the views. Watching the fireworks with the Chicago skyline in the background was unforgettable. After the fireworks, we sailed under the night sky with the sails up and great music playing. It honestly felt like I was in the Caribbean, except with an amazing city skyline all around us. I'm from New York and was in Chicago for work, and I have to say this was even more impressive than seeing the New York skyline from the water. I also own a sailboat, so I really appreciated how well the crew handled the ship. One of my favorite parts was that guests could even help hoist the sails. There was a full bar with a really good rum punch, and so many great spots to take pictures of the sunset and the skyline. The crew was also happy to take photos for people. If you're going, get to Navy Pier early and enjoy the restaurants and drinks before your sail. This is great for families, couples, or even if you're traveling by yourself like I was. It's a unique experience that you won't get on one of the regular tour boats. I would absolutely do this again the next time I'm in Chicago.

This boat ride was so enjoyable. The crew was awesome! Special shout out to Nina who went above…read moreand beyond to assist with my mom and aunt who are handicapped and had a great time. I highly recommend Tall Ship Windy!

SO MUCH FUN!! How it…read moreworks: 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!

We had an excellent charter experience with Captain Bill on a speedboat. Booking the boat was quite…read moreeasy 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.

I do not believe this is in business. I left a voicemail last summer and received no response. The…read moreodd part is his voicemail mentions the business name. Go look at the website link which is defunct. I am giving one stars because leaving a business page up on Yelp when it is no longer operational is a waste of customers' time.

It was a very fun experience! My friend and I were in…read moreChicago for the weekend only. Our original day of sail was canceled due to weather, but Captain Sanjay was very accommodating and we were able to go sailing the following day. We had a beautiful day and a great time drinking champagne and enjoying our time on the water. The captain and his first mate (his father) were great company and made us feel very comfortable. Captain Sanjay has a medical background in research and he is an athlete; he shared with us his knowledge about nutrition and sports, as well as the role vitamin supplements play in our daily activities. My friend and I are runners and we are currently training for the MCM marathon, thus his tips and recommendations were very useful to us. Our visit in Chicago ended with the sail and it was the perfect ending to a fun weekend!

If you're looking to charter a boat in Chicago, this is the place. They have a variety of options…read moreavailable and Captain Russell is fantastic. We did a 5 hour charter for 7 and part of me wishes it was longer. Pack your cooler, get your tunes ready to Bluetooth into the boats sound system and enjoy a nice relaxing day on Lake Michigan.

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!!

I found this boat charter on Yelp! Spoke with Paul and the process to book was so seamless! He…read moreanswered all my questions promptly when wondering how to tip and if we needed to bring coolers. They supplied ice for our trip which was great! At the end of our time we were already trying to book with them again! With the new adjustment we were able to have 30 with proof of vaccines! Highly recommend them!

Captain Paul and team was AMAZING! We had a post graduation cruise for my daughter and best friend,…read morecruising into the sunset. The most memorable trip for my daughter, friends and family. Captain Paul was extremely flexible in making the most beautiful experience. We cruised on both the river, and saw the sunset on Lake Michigan. The experience of a private yacht for my daughter's celebration was priceless. Thank you Captain Paul for your hospitality!