SAIL CHICAGO OWNS AND MAINTAINS A FLEET OF KEELBOATS that PROVIDE EXCELLENT STABILITY AND SAFETY FOR EASY HANDLING AND QUICK LEARNING.

Ideal 18

3 boats moored at Monroe Harbor

With convenient features like a furling, self-tacking jib and a self-bailing cockpit, the Ideal 18 is easy to rig and fun to sail. Stable and enjoyable with up to three people, the Ideal 18 is a no-hassle, well-balanced sailboat.

rhodes 19

The Sail Chicago fleet began with the purchase of a brand-new Rhodes 19 in the late 1950s. At its peak popularity, we had close to a dozen operating out of Monroe and Montrose harbors. As these boats have aged and required more maintenance, we have replaced most of them with Ideal 18s and Colgate 26s. But because the Rhodes 19 remains a solid, well-built design, you can still enjoy sailing our remaining ones out of Monroe Harbor.

3 boats moored at Monroe Harbor

8 boats moored at Monroe Harbor

Colgate 26

Sail Chicago's most versatile boat is the Colgate 26. With an outboard motor, large cockpit, furling jib, and small cabin for storage, these boats have all the amenities sailors love, with the simplicity and handling of a smaller boat. The Colgate 26 was designed for instruction, but also serves as a solid day sailor and racing boat.

1 boat moored at Belmont Harbor

Hunter 34

Priorities is Sail Chicago's 34-foot cruising boat. With a diesel engine, cabin with sleeping berths, a head, and a full galley, it is a popular choice for those interested in preparing for bareboat charters or simply looking to take a group of up to seven people out for an afternoon sail.

1 boat moored at Burnham Harbor

ERICSON 34

Calypso is Sail Chicago's 1993 Ericson 34 cruising sailboat built by Pacific Seacraft. She is a beautiful cruising boat, stiff in a good breeze and nimble in light winds. Similar to Priorities, Calypso sleeps five and features an inboard diesel, head, and fully functioning galley. Some of Sail Chicago's cruising classes are taught aboard Calypso.

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I always thought sailing was for rich dudes. yeah, no, not at sail chicago.

-Alejandro Jimenez