I've gone out sailing with Captain Conway on a few occasions with friends and family and just scheduled an outing with my coworkers from out of town. Mainly to show them why Chicago summers are the best. Conway showed us the best views of the museum campus, navy pier, and a skyline shot you just can't get anywhere else in Chicago (I recommend sitting up near the bow). He's shared stories of sailing on every coast of the country and has been sailing on Lake Michigan for years so I quickly figured out I didn't need to come with a plan. The boat was spotless, Conway and his crew were awesome, he had a fridge to keep my beer cold (Something I hold near and dear to my heart), Bluetooth speakers, sneaky quiet motoring in and out of the harbor so my friends can hear my bad jokes (I only have so many opportunities), and overall, Conway provides a safe stress-free sail. Pro tip: Whether you're trying to convince someone to move to Chicago or just remind yourself why you live here in the first place, Conway is the Captain to sail with! read more

When booking charters two things are non-negotiable: 1. A Savvy Captain 2. A Flawless Boat I have been renting summer charters in Chicago since 2004 and have seen more than a few duds. We stumbled upon Captain Conway several years ago and have asked for him by name from that point forward. He is a skilled sailor, knowledgeable Chicagoan, and genuinely laughs at bad jokes. He has a knack for quickly assimilating into any group dynamic and is one of the best color guys in the business. As far as the boat itself, Captain Conway is a bit of a perfectionist. Each boat is impeccably cared for, cleaned, and outfitted with premium fixtures and amenities throughout. I am always impressed by his attention to detail each and every time I step aboard one of the Captain's boats. In sum, the entire ChicaGo By Boat team cares and it thoughtfully shows throughout the entire process from booking to final approach. This is the place, and now you can tell your friends, you've got a guy. read more

This was our second year sailing with Captain Conway and we could not speak more highly of the experience! Captain Conway is delightful and punctual and fun and puts safety first. His boat is beautiful and spacious and fully equipped with cups/utensils/plates, anything you may need! Burnham Harbor was incredibly easy to get in & out of (we parked in the Shedd's lot- $30 for 4+ hours). We also arrived early enough to order food from Boat Drinks which we brought on the boat and enjoyed once sailing (allow enough time because Boat Drinks is not incredibly fast-- but worth it!). We already cannot wait to go sailing with Captain Conway again next year! read more

Nothing beats the sunset over the Chicago skyline! An A+ all around trip on the lake. I couldn't have asked for a better experience sailing with Conway - Not only was he super knowledgeable with the city and all things sailing-related, but the boat was very clean and he was prepared for everything including extra fleece jackets and blankets for us once the temperature dropped as the sun was setting! I have always preferred these sailing boats over the big cruise ships in Lake Michigan as they are way more personable with all the freedom to go where you want, but it feels good now that I finally have my go-to captain! read more

Looking for a sailing trip for our thirteen year olds birthday, there were many options that we explored. We absolutely made the best choice with Captain Conway! The boat was meticulous and it was obvious that it was well cared for. He was incredibly knowledgeable and made the trip so enjoyable! Leading up to our trip, I had made an error in scheduling and he was quick to respond and very accommodating to ensure that we were able to get the sail in. There will be no need to explore options in the future - ChicaGo by Boat will be are one and only call! A wonderful time was had by all! I couldn't recommend him more! read more

I HIGHLY recommend ChicaGo By Boat! Captain Conway called 1/2 hour before to introduce himself and make sure we didn't have any last minute questions. We scheduled our tour for Saturday night (8-11P) to celebrate my mom's 60th birthday, and this tour did not disappoint. Captain Conway was knowledge about Chicago and gave us a great tour of the lakefront. We also had a front row seat to the Navy Pier fireworks. Captain Conway made us feel safe and welcome on his boat. He was social with us without being intrusive. I CANNOT say enough great things about this company! read more

My wife and daughters surprised me with this gift for my birthday and as a sailor myself this was a perfect gift. Beautiful scenery and perfect weather for sailing. The Captain and his First Mate were very accommodating and made the cruise all that much better. The boat is very comfortable and sails very smoothly. This is the perfect experience for anyone who wants to see Chicago from the water without the crowds. read more

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. Don't! 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! read more

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! read more

The sail on a Friday afternoon was picture perfect. The boat was comfortable for my small group of two and Captain Conway was very accommodating. We were able to bring our own food and drink onboard. I recommend this tour for anyone looking to get out on the lake and experience Chicago from a different perspective. Absolutely beautiful! read more

We had a really nice time with Captain Conway on a morning sail with perfect weather. He always called us back promptly when we left questions on his voicemail and had no problems arranging the charter. He was friendly, fun to talk to and the boat was very well maintained! Will book ChicaGo By Boat again if we do another sail! read more

We had such a wonderful time on Captain Conway's sailboat!!! He and Tatiana made our Air and Water Show experience amazing. The boat was awesome and they both made us have a lovely time on Lake Michigan. We will definitely keep ChicagGo by Boat in mind for our next outing on the water!! Thanks again!!! TWO Big thumbs up!! read more

We really enjoyed our time on this boat. I've done a few charters in Chicago, and this was by far my favorite. The boat was beautiful, well maintained, and comfortable. Captain Conway was knowledgeable, friendly, and made the experience really enjoyable. Highly, highly recommend. read more

We truly enjoyed our experience. It was our first time sailing on Lake Michigan and Captain Conway did not disappoint. He was very personable and a great host. The views were beautiful. We felt comfortable and had a great time! We will definitely be returning! read more

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! read more

Captain Conway was as good as Captain as one would need for an enjoyable day on the water. This from a 40 year deepwater sailor on the Great Lakes. I am sure under any circumstance that you will enjoy the trip and return safely. Nice clean comfortable boat!!! read more

We have sailed with Captain Conway several times. His expertise fills you with confidence. His personality is laid back. I would recommend ChicaGo by Boat to everyone. Sailing Lake Michigan is an experience everyone should have when visiting Chicago. read more

Had a fantastic time out on 'Night Swimming'! The boat is a good size and held us comfortably. Captain Conway sailed us around the area with ease! Really enjoyed our time out on the boat and will be doing it again! read more

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! read more