The 10 Best Boat Rentals in Chicago, Illinois (IL)

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.

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!

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.

ChicaGo By Boat offers Chicago's premier affordable luxury boat charters. We invite private groups of up to six passengers aboard the S/V Nightswimming for two to three hours based on our guests' needs. Whether it's your first time, only time, or just the next time--we want your sailing experience with us to be the BEST time you have this Summer.

This is a great way to see Chicago from the other side of Lake Shore Drive. Cruise the Lake front for a sunset cruise. Watch the Navy Pier Fireworks on Wednesday or Saturday nights with the city skyline as your backdrop, Take a cruise down the river and marvel at the magnificent architecture. Or spend a day in the sun anchored in the play pen next to Oak street beach and the John Hancock building.

Knot My Boat Charters is a Chicago-based company that specializes in providing our clients with luxurious, yet affordable, boat charters and event accommodations. We provide expertise gathered from 12 years of captaining and 16 years of combined hospitality experience in Chicago. Our team prides itself in providing an exceptional full-service experience to all of our clients.

Wateriders is seasonally closed until April of 2019. As the pioneers of kayaking on the Chicago River, Wateriders has been hosting kayak tours for 21 years. Guests get an unbeatable view of the city's beautiful interior skyline as they paddle through the architectural canyon of downtown Chicago. Both guided tours and open rentals are available. Located on the riverwalk behind the East Bank Club in the River North neighborhood, Wateriders is ideally situated for making the most out of one's adventure, and is easily accessible by all means of transportation. Discounted garage parking available less than 2 blocks away,

The Chicago Electric Boat Company offers a unique, memorable and environmentally friendly way to see the great city of Chicago. By renting boats that are comfortable and easy to drive, the Chicago Electric Boat Company gives even new boaters a chance to get behind the wheel and see the city from this exceptional point of view.

Island Party Boat brings a touch of the tropics straight to Chicago. Its fleet of 10 Polynesian-themed boats accommodates anywhere from six to 90 guests, who head out on Lake Michigan or the Chicago River for hours of tropical fun. All of the tiki party boats are equipped with waterslides, and customers can expect other party-ready touches like bars, LED TVs, and premium sound systems.