A Florida Keys specialist delivery to the southernmost city in the continental US at Mile Marker 0. Chicago to Key West runs about 1,525 miles via I-65 South to I-75 South to US-1 South. Our anchor partner In-N-Out Keys runs the Overseas Highway daily and serves every address in Key West and surrounding mile markers door-to-door. No Homestead drop-off, no handoffs.
MM 0, Mile Marker Zero.
The I-65 + I-75 + US-1 S run.
Chicago to Key West is the primary Midwest snowbird lane. Most volume is Chicago residents with Keys second homes — North Shore (Evanston, Wilmette, Winnetka), Naperville-Aurora, and the western suburbs. At approximately 1,525 miles via I-65 South to I-75 South to US-1 South, the mainland portion is standard freight corridor; the Keys leg via the Overseas Highway is what makes this lane different.
Live route map — carriers run I-65 South to I-75 South to US-1 South door-to-door between Chicago and Key West. The Overseas Highway leg from Florida City to Key West runs through 42 bridges and 113 miles of single-road island chain.
Chicago → Key West rates.
Starting prices on this the southernmost city lane. The Keys leg has a $350 starting floor that covers the Overseas Highway itself. Key West at MM 0 is the deepest Keys destination — the full 113-mile Overseas Highway exposure. The daily FtL→KW lane keeps reliability high regardless.
Chicago → Key West shippers.
Real feedback from customers who’ve shipped to or from the Keys.
“Shipped from Lincoln Park to our place at Old Town. Driver knew the route and handled everything. Way easier than driving down ourselves.”
“Midwest snowbird run from the North Shore to Stock Island. Six days. Picked up on schedule, arrived clean. Quote stayed the same from start to finish. No surprises.”
“Tried other carriers who couldn’t actually deliver to Key West — wanted to drop in Homestead. ASNM connected us with a real Keys carrier who delivered to the driveway.”
Chicago → Key West FAQ
The questions Chicago-to-Key West shippers ask most. Have one that’s not here? Add it to your quote and a specialist will answer directly.
Where we pick up & deliver.
Door-to-door service on both ends. The Keys side covers every Monroe County address; if your area isn’t listed we almost certainly still serve it.