No Money Down/2.99% APR + $1K Trade Assistance

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What's happening

Time to Ride
Test ride a new H-Davidson motorcycle, Get a Limited-Edition Flag Read more
Rolling Sturgis to MKE
Get ready for the ride of a lifetime! From June 1 through July 31, enter for your chance to be part of Harley-Davidson's Rolling Sturgis to Milwaukee! Read more

TIME TO RIDE.
From June 1st through August 31st, take a test ride on any eligible Harley-Davidson® motorcycle and score an exclusive limited-edition Harley-Davidson flag while supplies last. Read more
Land Here. Ride Out.
Land here. Ride out. At Windy City Harley-Davidson®, your journey begins the moment you touch down. Step off the plane, step into the thrill, and feel the roar of a brand-new Harley® beneath you. Read more

No Money Down/2.99% APR + $1K Trade Assistance
On Select New 2025 Cruiser and Street Glide Models. Plus, $500 Hero Cash for Military and First Responders. Offer ends June 30, 2026. Read more

Windy City Harley-Davidson^®

Stop by today and find your next bike!

Looking for a dealership staffed by real riders who live the lifestyle? Windy City Harley-Davidson^® is your home for new and pre-owned Harley^® motorcycles, genuine parts, expert service, and everything you need to stay on the road.

Our team—many of whom have spent a lifetime in the saddle—brings unmatched knowledge and passion to every visit. Whether you're hunting for your next bike, dialing in upgrades, or keeping your ride in peak condition, we’re here to help you make every mile count.

Windy City Harley-Davidson^® is your all-in-one destination for bikes, gear, and rider support. Stop in today and experience the difference of a dealership built by riders, for riders.Find out Mor

Search inventory

Time to Ride

Rolling Sturgis to MKE

TIME TO RIDE.

Land Here. Ride Out.

No Money Down/2.99% APR + $1K Trade Assistance

Windy City Harley-Davidson®

Stop by today and find your next bike!

Windy City Harley-Davidson^®