CB
ChicaGo By Boat
Experience Chicago from the water with unforgettable sailing adventures on Lake Michigan.
5(5 reviews)
event-planner
$$$
Experience Chicago from the water with unforgettable sailing adventures on Lake Michigan.
ChicaGo By Boat offers premier sailing charters and tours on Lake Michigan, providing a unique perspective of Chicago's stunning skyline. Led by the experienced and accommodating Captain Conway, we specialize in sunset sails, private charters, and special events like proposals and celebrations. Our clean, well-maintained sailboat ensures a safe, comfortable, and magical experience for all guests. Whether you're seeking a romantic evening, a fun outing with friends, or a memorable way to view the Air & Water Show, we deliver exceptional service and breathtaking views. Join us for an adventure that captures the essence of summer on the water!
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Relaxing evening sails with panoramic views of Chicago's skyline as the sun sets over Lake Michigan.
Exclusive boat rentals for groups, perfect for celebrations, corporate events, or intimate gatherings.
Customized experiences for proposals, anniversaries, and other milestones, with photography services available.
Prime viewing charters during Chicago's annual Air & Water Show from the water.
Peaceful morning tours when the lake is quiet, ideal for serene sailing and photography.
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.
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.
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
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!
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!
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