Win a 2026 Harley-Davidson Street Glide — Illinois Harley-Davidson's Key-Try Giveaway

What you're looking at

The 2026 Street Glide is the bike Harley-Davidson's touring line is built around — the batwing bagger the company reworked in 2024 and has been refining since. Power comes from the Milwaukee-Eight 117: 1,923cc of 45-degree V-twin making a factory-quoted 105 hp at 4,600 rpm and 130 lb-ft at 3,250 rpm, fed through a six-speed Cruise Drive gearbox and a belt. The headline hardware sits inside the fairing, where a 12.3-inch Skyline OS touchscreen replaced the old analog cluster.

Nobody is going to call a Street Glide rare. It is America's best-selling bagger, and that is rather the point of it — the aftermarket is bottomless, every dealer can service it, and resale is about as predictable as motorcycling gets. What makes this one interesting is simply its condition: a new, current-model-year unit, zero-mile, with a factory warranty and no previous owner's decisions baked into it.

The rules don't publish a color or a trim. The $24,999 ARV is exactly Harley's base MSRP for the 2026 Street Glide, which reads as base spec rather than a Limited or one of the chrome-finish two-tones.

Why it matters

This is a five-dealership promotion. The rules name Woodstock Cycles LLC, Illinois Cycles LLC, Chicago Cycles LLC, Windy City Cycles LLC and Starved Rock Cycles LLC as "commonly owned and collectively referred to as the 'Sponsor'" — one Illinois dealer group, five stores, one bike. It also states plainly that Harley-Davidson Motor Company is not a sponsor of or affiliated with the promotion, which is worth knowing given how much bar-and-shield branding surrounds it.

Entry costs nothing. You visit a store, collect that location's weekly keyword, and submit it for one entry — once per person, per location, per calendar week, capped at 250 keyword entries for the whole run. Each store's Grand Opening carries a bonus keyword worth ten entries, which is where the marketing's "50 chances" figure comes from: five events, ten entries apiece.

The fine print worth knowing

Entries alone cannot win you this motorcycle. This is the term that changes what an entry actually buys, and the promotion page states it only in small type. Entries feed the finalist drawings, not the prize itself: "Two (2) finalists will be randomly selected at each listed Grand Opening event for a total of ten (10) finalists, and finalists must be physically present when their name is drawn to receive a finalist key or an alternate will be selected." Bank 250 entries from your couch and you still forfeit the slot if you aren't standing in the dealership when your name comes out.

Most of the finalist slots are already spoken for. The Grand Openings ran June 6 at Illinois Harley-Davidson, July 18 at Starved Rock, August 22 at Windy City and September 12 at Woodstock. Four events, eight of the ten finalists. The last two finalist keys are drawn at the fifth and final Grand Opening — October 10 at Chicago Harley-Davidson in Villa Park — and the key try happens at that same event. Entering now is a play for two remaining slots, and you have to be there in person to take one.

The key try is the real drawing. Per the rules, "all ten finalists will attempt to start the motorcycle using their chosen key, and the finalist whose key starts the motorcycle will be declared the Grand Prize Winner." Ten finalists, ten keys, one bike. The published rules do not state that exactly one key is guaranteed to fire the engine, nor what happens if none does — so treat a finalist key as a one-in-ten shot, not a certainty of a winner being crowned that afternoon.

You get the motorcycle and the tax bill. The prize is the bike only. The winner is "solely responsible for all taxes, title, registration, licensing, insurance, and any additional fees," will "receive an IRS Form 1099 for the ARV of the prize," and must provide proof of insurance before taking delivery. Budget for a 1099 on $24,999 on top of Illinois plates and a policy.

Four states are carved out. Residents of New York, Florida, Rhode Island and Hawaii are excluded — a routine move on a prize this size, since those states impose registration or bonding requirements on sweepstakes above modest prize-value thresholds. There is no cash alternative in the rules.

Dates: the promotion runs March 20, 2026 through October 10, 2026. No clock time or time zone is printed for the close; the practical deadline is the October 10 event at Chicago Harley-Davidson, so check with the store for its start time before you drive out.