My husband and I grew up sailing on Lake Michigan. We moved away 15 years ago and the lake is the thing we miss most. We met up with friends over Labor Day Weekend and I surprised everyone by booking a sunset sail with ChicaGo By Boat. Booking and communication was excellent. We totally lucked out with the most gorgeous evening of sailing! Highly recommend Conway, he was a lot of fun to sail with. Definitely the highlight of our weekend! Looking forward to sailing with him again.

Sailing on Lake Michigan is a true gift of summer. I love being on the water, taking in the views and enjoying sunshine. Morning sails are special, as the lake is quiet and the boats are few. But a good sail is fantastic anytime. I have sailed on SV Nightswimming with Captain Conway multiple times over the last few seasons. It is always a fantastic experience! He sails hard if wind conditions permit, and there is nothing quite like the power of a heeling sailboat. The views are absolutely stunning to boot! All of the customers' needs are anticipated and cared for. ChicaGo By Boat is a fantastic experience that I am fortunate to able to enjoy. HIGHLY RECOMMEND. Best in class.

Captain Conway was nice enough to open the COVID-19 delayed sailing season for me and my fiancée as we looked for a unique way to celebrate what would have been our wedding weekend. We sailed out of Waukegan harbor on a beautiful Sunday afternoon. Captain Conway hooked us up with a parking pass right next to the pier, had a bottle of champagne waiting on board for us, and took us out on a great cruise along the north shore. Not only was he a great and accommodating captain, he was a pleasure to just hang out and chat with for 3+ hours. We plan to do another cruise in the future with family and friends or just on another summer weekend date night. Highly recommend ChicaGO by Boat!

We had a totally magical time with Captain Conway for a surprise proposal! Beautiful ship, excellent sailing and all around a truly wonderful time. We will definitely book again for other celebrations!

We have had a great experience and everything was perfect. Our captain Conway is awesome and helpful. My group was sailing for 2.30 hours. We are looking forward sailing with Captain again. Good value, if you are looking for this I would highly recommend it. Thank you Captain :)

Captain Conway delivered a perfect sailing experience for our family, including a 6 and 8 year old. He's a genuinely nice guy who you can tell really enjoys being on the water himself. He reached out the morning of our trip to see if we had any questions, had the boat ready to go on-time, was knowledgeable about the city, and made some great recommendations for the rest of our time in Chicago.

We reserved for the Chicago air and water show. We could not have been more pleased with our experience. Captain Conway was so nice and accommodating we could not have asked for anything more the boat was so nice and clean blankets and rain gear provided. Definitely where u should book a charter we r going to book to sail soon

BOOK CAPTAIN CONWAY! He gave us such a special experience, I felt like part of the family. His boat is beautiful, and he made us feel safe while encouraging full enjoyment of the sail. So affordable, and you really can't find a better time sailing than with ChicaGo By Boat!

Chartering a boat had been on my wife's bucket list for a while, so we decided to check that one off for our anniversary. I found Captain Conway and ChicaGo By Boat on Google. The weather was rainy immediately prior to our scheduled outing, and Captain Conway called us well in advance to let us know that the weather was breaking, and would not interfere with our charter. Captain Conway even made sure that we had dry towels since we'd been out in the storm. Captain Conway is both very professional, and incredibly friendly. He was so accommodating with all of our needs and questions, good spirited, and just delightful to talk with. The Nightswimming is an absolutely beautiful boat, and the care and attention that the Captain gives to her is readily apparent. My wife and I had an unforgettable day out on the lake thanks to Captain Conway!

cannot say enough good things about this charter! my boyfriend and I did the sunset cruise on the 4th of July and it was one of the coolest experiences ever. Captain Conway is friendly, personable, professional, and skilled. would definitely recommend to anyone who wants a private experience out on the water. Will definitely be back!

Came across Captain Conway and Chicago By Boat by accident, but boy am I glad I did. I took my gf for a surprise sailboat ride for her birthday and it was amazing. Capt. Conway was accommodating, friendly, personable, and made our first time on a sailboat an unforgettable experience. If we do this again with friends or family, I will be booking with him and his company again!

Captain Conway is amazing! We took a beautiful Saturday late afternoon sail that started out mostly sunny but turned into storm front clouds. It was mesmerizing, and Captain Conway navigated each change with ease. He tailor makes each excursion. We asked him to explain his sailing techniques as he did them, and we loved learning from such a skilled professional–including the life lesson that if you meet resistance, don't keep trying to force something, but figure out the issue and find another way. We'll be back!

Captain Conway went out of his way to provide our party of 4 an exceptional outing, from giving us a heads-up about traffic and parking conditions, to delivering a smooth and enjoyable voyage accompanied by great tour guiding and wonderful conversations. The boat was pleasant, clean, and comfortable, and obviously maintained with much care and passion. We would absolutely recommend his services to anyone looking for a good sail in Chicago.

Excellent time on Lake Michigan. We had to reschedule our first appointment due to bad weather and were 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!

CHECK OUT THIS VIEW. Great vibes and very affordable! Definitely the best business we could have booked with to avoid one of those overcrowded tourist boats. Thanks guys!!

Captain Conway facilitated the most amazing experience for me and my Fiance on what became our most special night. I proposed to my then girlfriend last month and Capt. Conway was super responsive and accommodating even after a couple last minute changes. I can't forget to mention he's also a great photographer! The boat itself is absolutely gorgeous and spacious. The cabin and deck were super clean and we felt safe and comfortable even admist the pandemic. I highly recommend Capt. Conway's charter for a romantic night out or a friends get together. Either way I can promise you will have a memorable expierence!

Beautiful views and great engagement spot. It was our first time on a sailboat and it was a great experience. Captain Conway was friendly and accommodating. It was a wonderful way to end our trip!

Amazing experience. The captain knows the boat inside and out so it made for ‘smooth sailing’. A must-do when you visit Chicago.