Windy City Harley-Davidson

06/19/2026

Double event tomorrow? Absolutely!

The bag, water bottle, speaker, and multi-tool will be our raffles giveaway! The mugs will be free gifts for fathers, so make sure you come early and claim yours!

GREAT AMERICAN RIDE: We are throwing a party to celebrate over 120 years of freedom on two wheels, and you’re invited to join us. One day only, prizes and giveaways, multiple ways to win!*

REGISTER FOR YOUR CHANCE TO WIN**

-A LIBERTY EDITION HERITAGE CLASSIC MOTORCYCLE
-1 OF 12 $500 IN-STORE SHOPPING SPREES

Learn more: https://windycityhd.com/event/48624/great-american-ride

06/19/2026

Who said rain means no riding?🌧️

Gear up for any weather at Windy City Harley-Davidson!

06/18/2026

The color is called Envious Green Fade for a reason 😮‍💨

One look at this 2022 CVO Street Glide and it's obvious why everyone is jealous

This one DEFINITELY won't be around long, so call or visit Windy City Harley before she's gone!

Learn more: https://windycityhd.com/inventory/984500/flhxse-2022-cvo-street-glide

06/18/2026

Pump 3 diesel 🤣

06/17/2026

TAKE A TEST RIDE. WIN AN 85" TV! 📺

Your next Harley-Davidson test ride could come with a brand-new TV. Take a test ride on a NEW Harley-Davidson at Windy City Harley-Davidson and you'll be entered for a chance to win. It's that simple. Find your next ride, feel the thrill of the open road, and score a shot at upgrading your garage AND your living room.

Ride. Enter. Win.

See dealer for more details. No purchase necessary. Valid June 17th through June 30th 2026.

Take a test ride on a NEW Harley-Davidson at Windy City Harley-Davidson and you'll be entered for a chance to win.

06/17/2026

Welcome to the Windy City Harley-Davidson family, Cristian! 🤘

We’re excited to have you on the team. Be sure to say hello when you see him around the dealership!

06/16/2026

The nut pocket is an everyday essential around here 🥜

06/16/2026

Whether you play with friends or practice alone, this Harley-Davidson pickleball set will have you looking the coolest on the court 😎

Available now at Windy City Harley-Davidson!

06/15/2026

2021 Street Glide Special in Blackjack Metallic 😮‍💨♠️

Learn more: https://windycityhd.com/inventory/971480/harley-davidson-street-glide-special-2021-flhxs-black-jack-metallic

06/15/2026

We're halfway through June, so if you haven't heard about Retail for Trade, now's the time!

RETAIL FOR TRADE when Trading Up for a New Bike!

Ready for a new bike? With Retail for Trade, you could receive top value for your current motorcycle when trading up for a new Harley-Davidson. Bring in your bike for an appraisal and see how much it could be worth toward your upgrade!

Learn more: https://windycityhd.com/promotion/181519/retail-for-trade