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

TripAdvisor ranked Shoreline Sightseeing as the #1 Most Booked Tour in America! Shoreline Sightseeing is Chicago's leader in river and lake cruises! Featuring state-of-the-art tour boats and expert guides, Shoreline presents the Chicago skyline as you've never seen it before. With so many options among our lake and river cruises, we're sure to offer a tour your whole group will love. Our famous Architecture River Tours are led by knowledgeable and entertaining guides showcasing the city's rich architectural heritage. We also offer skyline lake tours, romantic sunset tours, and exciting fireworks cruises from which to see dazzling displays throughout the summer. Themed offerings include wine tasting cruises, brew cruises, 4th of July options, and St. Patrick's Day cruises. So set sail with Shoreline today, where every day is a celebration of Chicago!

Only the Chicago Architecture Center and Chicago's First Lady Cruises can showcase Chicago's world renowned city architecture with style, class and comfort on the official Chicago Architecture Foundation Center River Cruise aboard Chicago's First Lady. Open-air and air-conditioned seating is available. Learn about the architecture and design of over 50 buildings as described by CAC-certified volunteer docents/guides on this 90-minute tour that showcases all three branches of the Chicago River. Full-service bar aboard each vessel. All tours depart from the Chicago Riverwalk at Michigan Ave. and Wacker Dr. (southeast corner of the Michigan Avenue Bridge). Look for our blue awning.

Kayak Tours, Rentals, and Lessons on the Chicago River. Located on the Chicago Riverwalk. Enter Riverwalk at Columbus and Wacker. The second location on the lakefront at Monroe Harbor.

UPDATE: FOR MAXIMUM SAFETY AT THIS TIME, PLEASE CONSIDER OUR NEW PRIVATE TOUR. JUST YOU AND YOUR FAMILY AND FRIENDS. TEMPORARY LOW PRICE! See it ALL Chicago tours invites you to join us on one of our award winning Chicago mini bus tours. See Chicago in luxury, as you ride in one of our large windowed, climate controlled mini buses. Fun and informative guides, stops at several picturesque areas and the ability to ask your guide questions at any time make this a very popular tour. You will not only see the downtown sights, but also visit several interesting neighborhoods, including The Gold Coast and Lincoln Park. Three photo stops make this a tour that is not to be missed! Pickups and drop offs are available from most downtown hotels for the Mini Bus Tour. If you are going on the combination Mini Bus and Chicago River Architecture tour, the tour will conclude at the boat dock at Michigan Ave. and Wacker Drive. Almost all downtown hotels are within one mile of that location.

Sailboat charters in Chicago on Lake Michigan for up to 6 people.

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.

Come Sailing, Inc. is Chicago's premier private sailing charters. Daily sunset sails offer views of the skyline that can't be beat. Fireworks charters on Wed & Sat evenings in Chicago offer experiences not to be missed. Kick back and let our experienced crew treat you to spectacular sailing along Chicago's beautiful lakefront!

At BBQ Pontoon you can take a private, self-guided river cruise where you’re the captain! No strangers tag along. It’s just you, kicking back with some good friends, great food, and awesome views! Get a free pizza on every cruise! All of our boats have Bluetooth-enabled sound systems.

Climb aboard Chicago's largest sailing catamaran, Latitude Adjustment. 3rd Coast Charters offers private cruises and lessons for all ages and all occasions. You can enjoy your own exclusive experience with our catered Corporate Outings, Bachelor or Bachelorette parties and family gatherings utilizing our optional Yacht Concierge. From morning brunch to moonlight cruises and everything in-between, 3rd Coast Charters give you and your guests an experience that will last a lifetime. Make your special occasion memorable with one of our private cruises. Captain and crew promise a great day or evening out on the water plus concierge and catering options available to make it truly unforgettable!

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.