Rent a boat in Chicago at the best price

Where to sail in Chicago

With a boat rental in Chicago, you can discover the city’s history and great views from the water as well as explore the shorelines of Lake Michigan. Find a boat in one of the 10 beautiful marinas that make up the Chicago Harbor such as Belmun, Burnham, and 31st Street marinas.

• Navigate the Chicago River and admire some of the famous riverfront buildings- Marina City, Tribune Tower, Lyric Opera, McCormick Bridgehouse, Merchandise Mart, Grant Park, and Magnificent Mile
• Set sail on St. Patrick’s Day and navigate on a green Chicago River!
• Sail to Indiana Dunes National Lake Shore, and admire the sand dunes from the water.
• Saugatuck is a unique town with award-winning beach and scenic waterways.
• Cruise to Mackinac Island located in the north of the lake and visit the charming little town full of eateries, galleries, and plenty of history.
• Want to set sail in calm waters? Grand Traverse Bay is a must!
• New Buffalo is a beach town with plenty of entertainment and beaches to relax on.
• Rent a boat for a few hours and enjoy fireworks as well as Chicago’s skyline from the lake.
• Set sail for Lake Michigan’s western shore towards Door County, Wisconsin, a popular boating destination in the summer with lots of activities and events.
• For those feeling adventurous and wanting to set sail on a longer trip, consider sailing America’s Great Loop. The Southern part of Lake Michigan opens into the Mississippi River, allowing boaters to start their long-term journey.

What is there to see and do in Chicago, Illinois?

After you have explored Chicago, Illinois and Lake Michigan by water, there are still many things to see and do by land!

• Take some time to walk around the Art Institute of Chicago as well as the Museum of Science and Industry.
• Get an up close view of the iconic Cloud Gate or the ‘Bean’ and Millennium Park.
• Head for the Clouds and admire a 360° view of the river & city from the Willis Tower Skydeck.
• Relax at some of the nicest beaches in town like Oak Street, Osterman, and North Avenue Beaches.
• Spend an afternoon riding a bike or walking along the Chicago Riverwalk, home to many restaurants, bars, and shops.
• Have a day of fun at the Navy Pier, one of Chicago’s top attractions with food, entertainment, and rides.

When should I charter a boat in Chicago?

With more than 26 miles of lakefront and 29 stunning beaches, the best time to go boating on Lake Michigan and around Chicago is during the warm summer months. From May to September, visitors can soak up the sun, as well as relax on the beaches and practice water sports. For the warmest waters around +70°F, rent a boat in the months of July and August.

Can I rent a boat with a captain?

Avoid typical crowded boat tours and instead rent our own private boat with a captain who knows the city of Chicago and its surroundings like the back of their palms. By using Click&Boat, you can find a variety of boat charters with captain and/or crew.

Sit back and enjoy your time on board, no need to worry about navigating, docking, and anchoring. Chartering with a captain is the perfect option for those who do not have boating experience and qualifications as well as for those who would rather relax during their trip.

The request of a captain (and crew!) may come at an additional price depending on the size of the vessel, number of crew members and if there are any specific requests.

Where to rent a boat in Chicago?

With Click&Boat, the leading boat rental service, you can find a large range of boats, from motorboats to large catamarans to set sail in and around Chicago.

A yacht charter in Chicago, whether it is with a private or professional owner has never been so quick and simple. All you need is a few minutes to search and book the boat of your dreams!

Rely on our platform’s integrated messaging tool for our owners and renters to connect, up-to-date availabilities and prices, and a team of expert advisors who stand ready on deck to help you plan your next sailing holiday.

Opting for Click&Boat for your next Chicago boat rental will allow you to save money too- rental costs can be up to 40% lower than those offered by traditional agencies. So what do you say, are you ready to set sail with us?