⚡ $499 NATIONWIDE SHIPPING ⚡ BAD CREDIT OK ⚡ TEXT JOE: 414-439-6211
NEW HARLEYS DROP DAILY — FOLLOW ON TIKTOK & IG TO NEVER MISS ONE. $499 SHIPS TO CHICAGO.
Don't see what you want? Follow — new bikes every day. Ships to Chicago for $499.
See every bike as it drops. Prices, specs, and real videos. Ships to Chicago for $499.
Get notified when I drop a new bike — first dibs + $499 shipping to Chicago
Get notified when I drop a new bike — first dibs + $499 shipping
Or just text Joe directly: 414-439-6211
Why Chicago riders love used Harleys from Milwaukee starts with being just 90 miles north – close enough to trust, far enough to offer better prices. Chicago's streets are tough on bikes – potholes, heavy traffic, salt in winter. The city's mix of Lake Shore Drive cruises, highway commuting, and suburban runs demands motorcycles that are inspected, proven, and ready for everything from city traffic to long highway miles.
Chicago riders know quality because they ride in some of the toughest conditions – potholes, traffic, salt, temperature swings. Every used Harley we ship to Chicago gets comprehensive inspection – frame integrity, engine compression, transmission smoothness, brake systems, electrical. The Street Glide's wind protection and premium audio make it perfect for Lake Shore Drive cruises and highway commutes, while the Road Glide handles crosswinds off Lake Michigan better. Both models are proven on Wisconsin roads, so Chicago's conditions are no problem.
Shipping from Milwaukee to Chicago takes just 2-3 days via insured professional transport. We handle title transfer, paperwork, and registration assistance. Your bike arrives ready to ride – no dealer markup, no hidden fees, just transparent pricing plus $499 flat-rate shipping. Chicago dealers charge premium prices, but we're so close you can even come see the bikes in person if you want.
Chicago riders consistently choose us because we're transparent, we respond fast (text Joe at 414-439-6211), and every bike ships with our 48-hour guarantee. If something's not right, we fix it or refund it – no hassle, no questions asked. That's the difference between buying from someone who knows bikes versus a corporate dealer focused on moving inventory.