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 :)

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!

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!

Conway is an amazing host and captain. We had a blast and learned a lot. What a wonderful time, wish we could go more often.

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!

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!

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 cant forget to mention hes 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. Conways charter for a romantic night out or a friends get together. Either way I can promise you will have a memorable expierence!

My wife and I chartered the boat for an early morning ride. It was wonderful. We sat on the bow of the boat and enjoyed the experience!

Chartering a boat had been on my wifes 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 wed 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!

We had a great time! It was a wonderful way to celebrate two graduations. The boat is beautiful and Captain Conway is very friendly and responsive. I definitely recommend booking ChicaGo By Boat for your special occasions!

Not only was the tour itself a wonderful time but the service provided by Captain Conway was fantastic from the moment of booking to docking back in at the end of the tour. He took care of everything and not only did he answer any and all questions leading up to the tour candidly and promptly, but his sailing experience and attention to detail as a host helped make the evening a truly unforgettable one for my fiancée and I. Just an incredible experience!

We had a wonderful time!! Highly recommend using ChicaGo By Boat for your next sailing adventure. We will definitely be recommending this company to our friends and family. Easy to book, the boat was very clean and the captain was very professional. Great customer service and great vibes.

Fantastic tour! Amazing sunset view of the city.The captain was very friendly and professional. He even gave us great food and drink recommendations for dinner.

Captain Conway took my friends and family on an awesome evening trip with amazing views of the Chicago skyline. He was always happy to answer questions about the boat and discuss restaurant and bar suggestions in town (which were awesome when we tried them). Definitely recommend this to anybody visiting Chicago and even locals looking for an enjoyable evening.

Captain Conway is the real one. What a great experience. Having done 5+ Lake Michigan boat tours I can say this was by far the best! Will be a repeat customer.

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!

Perfect was the word I kept using to describe our time on the boat, because it absolutely was! My boyfriend and I had a great and relaxing day and Captain Conway was accommodating, friendly and extremely knowledgable. The boat is well taken care of and clean, and its obvious that there is tremendous pride taken into the company.Captain Conway, thank you for the fun conversation and making our day special. We will definitely be back and I highly recommend you and ChicaGo by Boat to friends and family!

I was able to take my girlfriend last Friday. This was the best date that we have ever had thanks to Captain Conway! The skyline was so perfect this night. Also, if you worried about getting cold. Dont! Captain Conway provides fleece jackets to keep you warm. The captain was also very knowledgeable of Chicago. The boat was spotless. Everything was perfect. Thank you for a wonderful evening!

Highly, highly recommend! Captain Conrad was so wonderful and accommodating. Made my dads birthday surprise go off without a hitch. Followed up before we arrived and helped us feel informed and safe on the boat. Would recommend them to anyone for a special day!!

Captain Conway was top notch! Proposed to my now fiance on the charter, and Captain made sure everything went as planned. Very personable, professional, and accommodating. He also knew exactly where to stop the boat for the fireworks. Well worth the price!

Ive always wanted to see the Chicago skyline from the water and sailing with ChicaGo By Boat was the perfect way to do so! Captain Conway is insightful, professional, and makes sure everyone is well taken care of. The entire trip was laidback and relaxing with beautiful views. I cant wait to get back on the water with ChicaGo By Boat again!

Awesome experience! Captain Conway was the perfect host for a really fun afternoon. Thanks!

Loved our time out on Night Swimming. Captain Conway was fantastic and made sailing around Chicago waters a breeze! Definitely recommend and will be going again!

Beautiful boat, knowledgeable and friendly captain, great way to see the city. Highly recommend!

Had the best night sailing - Beautiful boat, great views of the skyline, and great chatting with Captain Conway. Would and will 100% sail with Captain Conway again

The view was at its best, One of the best place to visit in the town.

A+! Sailing as it should be from booking to disembarkingTrust Capt, Conway and ChicaGo By Boat for all of your sailing needs!Sailing is kind of my thing. Theres nothing like relaxing out on the water with friends as we enjoy the inspiring views of Chicago. Im not talking about a booze cruise. Sure, you can find those all over town.My first summer in Chicago I met friends with sailboats and was converted from the idea of a booze cruise to the perfect floating patios with close friends and instead of crowds.Ahoy! Enter ChicaGo By Boat.I first went sailing on a semi-private charter with a visiting friend: Its a fine way to mingle and take in Chicago from Lake Michigan. Its also an excellent intro to sailing.I was invited me to try a private charter. Fortunately I knew of some friends who would join me.The owner Captain Conway always make me and my guests feel like VIPs from booking to boarding to disembarking. Theyre very professional, responsive and flexible. Whenever theres a weather concern theyve called ahead and communicated to give us the latest details before heading to Burnham Harbor.Captain Conway is very welcoming so its more like entertaining and sailing with friend, than a generic charter or a set tour around the pier. He works with all levels of comfort with water, sailing and athleticism. Conway also has some entertaining stories of people places things that have come up under sail.Sporty, lively and heeling? Check.Relaxing and enjoying the skyline views? Absolutely!BYO summer menu with paired beverages and tastings? Theyve become a stellar go-to summer choice.Summer birthdays aboard SV Nightswimming? This is certainly a luxury sailing vessel and first class event!They have several ways to let party hosts relax and lighten the load. When we have a group of 6 we can get an extra crew member to help. Theres bottled water for us as well as a refrigerator, ice and plastic drink ware.Have a VIP, corporate client or question about the best kind of sail for your group? Captain Conway and his team have always been able to help!With this relaxed and professional vibe everyone is instantly at ease and guests ask when we can sail next. Sometimes my guests and I enjoy a cocktail skyline sail, other times its water, Pellegrino and an athletic day finding the best wind.Plus, the wind and the waves conjure up an ideal mix so its like a built in spa day!And, its wonderful to see more social media support for sailing.Thanks for everything Captain Conway and ChicaGo By Boat!Sailing in these conditions again? YES, please!See you soon + fair winds!

Wonderful evening sail with Conway!