Windy City Boat Rentals | Top Boat Rental in Chicago, IL Skip to content

Windy City Boat Rentals

5901 N Sheridan Rd, Chicago, IL 60660

About

Windy City Boat Rentals offers an exciting opportunity for those in Chicago looking to enjoy a day on the water without the commitment of ownership. Specializing in boat rentals, the company provides a range of options including pontoons and speedboats, ideal for family boating or a fun outing with friends. With flexible rental durations, you can choose the perfect amount of time to explore Lake Michigan and the scenic Chicago skyline.

Conveniently located in the heart of Chicago, Windy City Boat Rentals makes it easy to indulge in a unique boating experience right in the city. Whether you’re planning a leisurely afternoon or an adventurous day on the water, their fleet and professional service ensure a memorable outing for both locals and visitors alike. Consider them for your next aquatic adventure and enjoy the best boat rentals Chicago has to offer.

Features

  • Ideal for family outings
  • Scenic lake views
  • Variety of boat options
  • Flexible rental durations
  • Located in downtown Chicago

Amenities

  • Anchor
  • Bimini top
  • Bluetooth stereo
  • Cooler storage
  • Depth finder
  • Fishing rod holders
  • Fuel included
  • Life jackets
  • Safety gear
  • Swim ladder

Why book with us

  • Relax with our hassle-free rentals
  • Feel secure with our safety features
  • Choose from a variety of boats
  • Make memories on Lake Michigan
  • Experience scenic Chicago like never before

Frequently Asked Questions

What's included with a rental at Windy City Boat Rentals?

Rentals from Windy City Boat Rentals include life jackets, safety equipment, an anchor, fuel, cooler storage, a bimini top, a swim ladder and a Bluetooth stereo. Amenities vary by boat and by season, so confirm what comes with the boat you book.

How old do you have to be to rent a boat in Illinois?

Illinois law does not set one rental age for every boat: under the Boat Registration and Safety Act, no one under 10 may operate a motorboat, including personal watercraft, while a livery may not rent personal watercraft or specialty prop craft for operation by anyone under 16.

For a motorboat over 10 horsepower, ages 10 and 11 need direct on-board supervision by a parent, guardian, or parent-designated person at least 18. At 12, an operator may go without supervision by holding a valid boating safety certificate; ages 12 to 17 may instead use that supervision. Certificate rules also depend on birth date, though renters may qualify through approved abbreviated instruction. The rental operator sets its own minimum, so confirm it when booking.

Source: Illinois Department of Natural Resources (dnr.illinois.gov)

Do you need a boating license in Illinois?

Yes. In Illinois, anyone born on or after January 1, 1998, must have a valid boating safety certificate to operate a recreational motorboat over 10 horsepower, including a personal watercraft. No one under 10 may operate a motorboat. Ages 10 and 11 need direct onboard adult supervision; ages 12 through 17 need a certificate or qualifying supervision. A rental business cannot rent a personal watercraft for operation by anyone under 16. Licensed rental operators may give approved abbreviated safety instruction instead, allowing that renter to operate that livery’s rental without the certificate for up to one year. Common exemptions include qualifying nonresidents visiting up to 90 days and recognized out-of-state certificates. The Illinois Department of Natural Resources administers the program.

Source: Illinois Department of Natural Resources (dnr.illinois.gov)

Where can you go boating from Chicago, Illinois?

From Chicago, choose Lake Michigan for open-water cruising, the Playpen for a no-wake anchoring stop, or the Chicago River for a bridge-lined urban route. The Playpen lies between Ohio Street Beach and Oak Street Beach within Chicago Harbor and includes Anchorage A; it is often busy with rafted recreational boats. The Chicago Harbor Lock at the river mouth links Lake Michigan with the inland waterway system. For a lakefront start, DuSable, Monroe and Burnham harbors sit close to downtown; Diversey Harbor is the more sheltered option inside Lake Shore Drive, with bridge restrictions that limit it to powerboats.

Source: U.S. Coast Guard (navcen.uscg.gov)

What are the most popular boating destinations near Chicago, Illinois?

Boaters from Chicago often choose three Lake Michigan stops: the Playpen, Navy Pier Marina and 59th Street Harbor. The Playpen, between Ohio Street Beach and Oak Street Beach, draws recreational boats that anchor and raft together. Navy Pier Marina provides transient docking steps from the pier’s restaurants, entertainment and attractions. At 59th Street Harbor in Jackson Park, visiting boaters can use transient dockage and walk to the Museum of Science and Industry or 63rd Street Beach.

Source: U.S. Coast Guard (navcen.uscg.gov)

Location

5901 N Sheridan Rd, Chicago, IL 60660

Disclaimer

This listing was created using artificial intelligence and publicly available data. The information presented may be inaccurate, outdated, incomplete, or incorrect. Slipstream does not verify, endorse, or guarantee the accuracy of any listing content, including but not limited to contact information, pricing, services offered, hours of operation, or business status.

All content is provided “as is” and without warranties of any kind, express or implied. Slipstream expressly disclaims all liability for any loss, damage, or reliance arising from the use of this information. Users are solely responsible for independently verifying all details directly with the business.

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