The Salty Dog Sailing Co. | Top Boat Rental in Chicago, IL Skip to content

The Salty Dog Sailing Co.

1559 S Lake Shore Dr, Chicago, IL 60605

About

In Chicago, The Salty Dog Sailing Co. operates private sailing charters on Lake Michigan from Burnham Harbor. Instead of a self-operated pontoon rental or jet ski rental, it offers a captain-led sail aboard Peony, a 33-foot Dufour 325 Grand Large. The company welcomes couples, families, and small groups for two-hour outings, with charter options described for parties of up to six. Guests meet at Dock N on Burnham Harbor’s south side, near Soldier Field and McCormick Place.

Its sailing trips can suit dates, proposals, family celebrations, or time spent viewing Chicago’s skyline from the water. Morning, afternoon, evening, and sunset departures provide several ways to schedule a day on the water, while the captain manages the sailing. Parking passes are available for parties. For a boat rental near Chicago focused on private sailing, contact The Salty Dog Sailing Co. to arrange a charter.

Features

  • Private sailing charters
  • Captain-led charter outings
  • Small group sailing
  • Sunset sail planning
  • Chicago skyline viewing

Amenities

  • Waterfront & Access
  • Parking
  • Staff & Service
  • Fleet & Boat Types
  • Seating & Comfort

Why book with us

  • Celebrate special occasions with a private sail
  • View Chicago’s skyline from Lake Michigan
  • Plan a relaxing morning afternoon or evening
  • Depart from Burnham Harbor near Soldier Field
  • Bring couples families or small groups

Frequently Asked Questions

What's included with a rental at The Salty Dog Sailing Co.?

Rentals from The Salty Dog Sailing Co. include life jackets, safety equipment, cooler storage and dockside assistance. 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

1559 S Lake Shore Dr, Chicago, IL 60605

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.

Own this business?

Claim your listing now.

Manage your profile, showcase your rentals, and reach more customers.

More boat rentals near Chicago

Dor Sea Tours

Dor Sea Tours

Chicago, Illinois
2 W Belmont Harbor Dr, Chicago, IL 60657
Rent Chicago Boats

Rent Chicago Boats

Chicago, Illinois
Follow our signs to GREY DOCK, 900 S. Wells, Marina, Chicago, IL 60607
Free to inquire · No obligation