Rent a Boat in Chicago, IL

Chicago offers a front-row seat to one of the world’s great skylines. Cruise the Chicago River past the Willis Tower, drop anchor in the famous “Playpen” off Oak Street Beach, watch Navy Pier fireworks from Lake Michigan, or slip through the Chicago Harbor Lock for a lazy afternoon in the protected harbors stretching from Monroe to Diversey.

What to know

The most popular boat rental styles in Chicago include:

• Motor yachts and express cruisers for skyline photo shoots, sunset cocktails, and Playpen raft-ups.

• Pontoons, deck boats, and RIBs—perfect for mellow river cruises, architectural tours, and sand-bar picnics.

• Classic sailboats and catamarans for laid-back afternoons under canvas or Wednesday-night beer-can races on the lake.

If you’re new to the area’s shifting winds, commercial traffic, and the lock system that connects the river to Lake Michigan, consider hiring a USCG-licensed captain who knows local regulations and the best spots for unobstructed skyline views.