Things to do in Chicago, Illinois (IL): The Best Boat Tours & Water Sports

Windy City Sailing provides World-Class sailing and power yacht charters for recreational, romantic and educational experiences to individuals and small groups of up to 10 people. Experience the thrill of sailing and Chicago sightseeing with United States Coast Guard certified captains on our custom yachts. Our charters are personal and private for your group, family or clients.

We provide a private Yacht for fishing charters on LAKE MICHIGAN, right Downtown Chicago. WE provide all the gear and even clean your catch. You bring a lunch and beverages. The boat takes a group of up to 6 passengers. Trips leave at 6am and 1pm Salmon and Trout are the target species.

Try the best BYOB in chicago in front of the Chicago skyline and share a weekend adventure with family and friends, Seabreeze will customize the ultimate sailing experience for you. Bring your kids for a fun experience on the water, Enjoy the fireworks from a beautiful new perspective, Share an exclusive romantic date with someone special. Voted the best charter in Chicago!!!

Salmon and trout charters out of Belmont Harbor(North),in Chicago, on Lake Michigan. We provide all of the fishing gear and clean and package the fish after the trip. All you need to do is show up and we take care of the rest!

Sailing out of Belmont Harbor in beautiful Lincoln Park, take in breathtaking views of the city and relax in the serenity that only comes from being on the water. A professional captain ensures your day on the water will be safe, exciting and memorable. Our modern sailboat is sturdy, spacious and clean, with all the amenities required for a fantastic day on the water.

Experience Chicago's waterways like never before. Cruise aboard one of Chicago Classic Boat Charters' vintage vessels and take a step back into boating history. "Grace" was the 7th hull that the now legendary builder Hatteras ever built. "Naida" provides a glimpse into the glamor of the classic wood motor yachts of a bygone era.

Experience Chicago's lesser known side, Lake Michigan. Our passion is fishing Lake Michigan for trophy Salmon and Trout. We offer charter fishing trips out of downtown Chicago. We are located in Belmont harbor.

Chicago Sailing is proud to be Chicago's premier public sailing facility! With a fleet of over 23 sailboats ranging from 22'-53' we offer sailing lessons, captained charters, and rentals. Chicago Sailing is a US Sailing certified school and teaches to the highest standards in sailing. Group and teambuilding events are also available upon request, we regularly handle groups of up to 60 people.