Book your Chicago boat rental and check out our 'kinda' boating town

Grab your Chicago boat rental and head out on Lake Michigan for diving, windsurfing, fishing and soaking up the sun from the deck of your boat rental.

Choose from a Featured Chicago boat rental

2007 37' Sea Ray

She's perfect for your Chicago boating excursion that include Fishing, Waterskiing, Dining, Snorkeling, Cruising, or Sightseeing.

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Beneteau 393

Set sail on this beauty and your summer in Chicago won't soon be forgotten! She holds up to six, comes with all the toys you need to have fun in the windy city.

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Carver 36

Located at Burnham Harbor, right by Shedd's Aquarium as well as the public beach on Lake Shore Drive, she’s the ultimate in boating luxury.

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Discover how easy it is to arrange a Chicago boat rental for the perfect afternoon or weekend getaway.

Your Chicago boat rental includes:1,000’s of Boats: sailboats to yachts to center consoles, Largest Network of Licensed Captains, World-class insurance & 24-hour free cancellation. Plan your Chicago itinerary with these tips from the boating experts at Boatsetter.

Diving in Lake Michigan

Southern Lake Michigan has a number of wrecks ideal for diving. If you’re a novice diver Boatsetter can connect you with a captain who can provide the equipment and knowledge for your Chicago diving trip on Lake Michigan. In no time you’ll be navigating and exploring sights hidden from the surface of the windy city.

Chicago Sunbathing

An adventure is always better in the sun. Even when the weather is chilly being out on the water in the warm sun is enough to be a vacation all on its own. You can enjoy the sunshine from the deck of your boat rental or from a float in the water (if it’s warm enough, of course).

Fishing in the Windy City

The Chicago waterways are home to a variety of Salmon and Trout. There is something delicious to be caught all year long! You can fish directly from your Boatsetter Chicago boat rental with the help of a certified captain, or go it alone with your best fishing buddies. Dinner anyone?.

Sailing in the city of Big Shoulders

Sailing in Chicago waters is a popular pastime. You can rent a sailboat using Boatsetter and join thousands of Chicago sailors. If you’re not already, you’ll be a local in no time! Never sailed before? No problem. We can connect you with and certified captain so all you have to do is show up and enjoy.

Water Sports on Lake Michigan

Water skiing and tubing are the ultimate boating activities and guaranteed to make the entire family laugh. You must have a spotter on board for both activities and if you need assistance safely navigating the boat, hire an experienced captain when making your Boatsetter reservation.

Swimming on Chicago's Beaches

Swimming is not only a great activity for children, but also a good source of exercise and relaxation for the entire family. The beaches are typically crowded, especially in high season. Instead, jump in from the deck of your boat rental. It will seem like you have the entire ocean to yourself. Now that’s paradise!

Coast Guard-Licensed Captains

We match renters with captains seeking experiences on the water.

24 Hour Free Cancellation

Enjoy worry-free booking! Things happen. We offer free 24-hour cancellation on all boat rentals.

World Class Insurance

All Boatsetter rentals include the best insurance coverage available from beginning to end.


Browse our Chicago fleet or any of our worldwide boating destinations.