Top 10 Boat Tours & Water Sports in Downtown / The Loop, Illinois (IL)

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.

Just Sailing Ltd. exists to facilitate incredible sailing adventures on Lake Michigan. We loooove sailing. We love sailing because it is simultaneously exciting and relaxing. We love sailing because its fun when its warm and sunny, and its fun when its rainy and gray. We love sailing because it is the fastest way to get out of the city, into the quiet of the majestic Great Lakes. We love sailing because it allows us to feel the power of natural forces, and harness them with skill and intuition.

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

Experience the other side of Lake Shore Drive We offer completely customized boat Charters and Rentals. We have multiple boats ranging from 37' to 50' in length. Cruises start at 1.5 hours for a wonderful skyline tour of Chicago.

Book your charter with us any weekday evening, weekends and holidays! See the beautiful Chicago skyline from our sailboat and enjoy the fresh air on the Lake! Our sailboat can be reserved for up to 6 people and it comes with a coast guard license Captain.

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!

Why Us? We provide two of the same party boats, each for 24 people. You can combine them together for your special bigger event. Both boats have bars with ice, grill, dancing pole, disco lights and speakers with bluetooth. PARTY BOATS CHARTERS, PRIVATE CRUISES, BACHELORETTE PARTIES, BIRTHDAY WEDDING CEREMONY by CAPTAIN, PARTIES CORPORATE PARTIES, GRADUATION PARTIES, SPECIAL EVENTS, LUXURY YACHT SAILING, LEARN SAILING.

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!