Chicago to Key West Car Shipping

Chicago to Key West is a long southbound run that ends in one of the most particular delivery cities in the country. The driving distance is roughly 1,500 to 1,600 miles, and most of it is interstate. The last stretch is the Overseas Highway to Mile 0, then a handoff on streets that were never designed for a full-size car carrier, which is why many Chicago-area travelers fly out of O’Hare or Midway and ship the car instead.

Key West Auto Shipping is operated by In-N-Out Keys LLC, based at 9981 Overseas Hwy, Marathon, FL 33050, and serving the entire Florida Keys from MM 0 to MM 112. On a Chicago shipment, a trusted, licensed partner carrier handles the long haul to Florida, and our own truck takes the Keys leg and makes the Key West delivery. You deal with one team from quote to drop-off.

For a broader look at arriving on the island, start with Ship a Car to Key West. This post is about the Chicago origin and about three Key West delivery situations that come up constantly: Old Town, NAS Key West, and Stock Island.

How a Chicago-to-Key West shipment is structured

The partner carrier we name before you book loads the car in the Chicago area and brings it to Florida. In-N-Out Keys then runs the final leg down US-1, across the 18-Mile Stretch and the Seven Mile Bridge, and onto the island.

Mainland trucks often treat South Florida as the end of the line. Key West is still more than 100 miles beyond that, on a two-lane road with bridges and weekend backups, so the last mile has to be planned as its own job.

Step	What happens	Who handles it
1. Quote	You share your pickup ZIP, Keys address, vehicle and a preferred window. We confirm the plan and name the partner carrier before you book.	In-N-Out Keys
2. Pickup	The partner carrier loads the car in Chicago or the suburbs, at your address or a nearby lot.	Licensed partner carrier
3. Long haul	The car travels the interstate leg to Florida.	Licensed partner carrier
4. Keys leg	Our truck runs US-1, the 18-Mile Stretch and the Seven Mile Bridge to Key West.	In-N-Out Keys’ own truck and driver
5. Delivery	Walk the car together, in daylight if you can, and compare it with your photos and the bill of lading before you sign.	You and our driver

We will give you a realistic window rather than a promised number of days. A pickup window of a few days is much easier to place on a truck than a single afternoon.

Pickup in Chicagoland

We arrange pickups in the city and throughout the suburbs, including the North Shore, the western suburbs, and communities near O’Hare and Midway. A transporter needs space to park and drop a ramp, which is hard to find on a tight city block or in a low-clearance garage.

If your building is a poor fit, we will usually set a meet at a nearby lot with access to I-90, I-94, I-55, or I-80. Tell us about loading-dock rules and garage height when you book.

Snowbird timing, and the trip back to Chicago

When	Direction	What to know
October – December	Southbound	Busiest stretch for Chicago-to-Key West snowbirds. Book early and offer a pickup window of a few days.
Thanksgiving – New Year	Southbound	The tightest weeks. Trucks fill quickly and northern weather can delay a pickup.
April – May	Northbound	Return season. Mention your spring dates when you book the trip down.

When you are ready to send the car home, Auto Shipping Near Me maintains a Key West to Chicago route page, and we can help arrange the Key West pickup. Our post on shipping a car out of Key West after the season covers the island side of that move.

Old Town, NAS Key West, and Stock Island

Old Town

Old Town is beautiful and, for a car carrier, tight. Many streets are narrow, one-way, and lined with parked cars, low limbs, and overhead lines, so a loaded transporter cannot always stop in front of a cottage or guest house. That is normal, and we plan for it.

Sometimes the truck can get close; sometimes the meet is a nearby corner or the old Sears center lot on North Roosevelt Boulevard, one of the larger places on the island to unload safely. Our guide to Old Town Key West car delivery explains how those decisions get made.

NAS Key West

Military families moving to Naval Air Station Key West have an extra layer: base access. A driver may not be able to enter Truman Annex, Boca Chica, or other installation gates without the right credentials. The usual solution is a planned meet just off base, often at a public lot such as the one on North Roosevelt, where you or your sponsor can take the car through the gate.

Have your report date and a backup contact ready when you request a quote. See Military PCS to Key West and the NAS Key West PCS checklist for the rest of the move.

Stock Island and the immediate Lower Keys

Stock Island, at about MM 5, is a different delivery environment from Old Town. There is more industrial and commercial space, and many addresses are easier for a truck to approach, though marina lots and tight residential pockets still need a look in advance. Share any gate, dock, or after-hours details early. Our Stock Island and Lower Keys auto shipping page covers MM 5 through MM 33.

Open or enclosed, and how to prepare

We will walk you through that plan before you book.

Before pickup

• Wash the car (including the underside if you can) and take your own dated photos
• Leave about a quarter tank of fuel
• Remove toll transponders, valuables and documents
• Personal items are restricted by federal rules; some carriers allow a modest amount by agreement, often up to about 100 pounds, so confirm before pickup

At delivery, inspect the car in daylight if you can and compare it with your photos and the bill of lading before you sign.

What it costs, and how payment works

There is no single Chicago-to-Key West price, because the number depends on the vehicle, your pickup and delivery addresses, the time of year, how flexible you can be, and whether you choose open or enclosed transport. The reliable way to get a number for your dates is to request a quote.

Most carriers accept COD (usually certified funds: cashier’s check, money order, or cash), but fewer take billed payments, so paying the balance on delivery lets us line up the best carrier for your route. Your quote spells out any deposit and what is due and when.

Request a Chicago-to-Key West quote

Share your Chicago-area ZIP, the Key West delivery address or meet preference, the vehicle, and a preferred window. Request a quote or call (754) 714-2439. You can also email tony@in-n-out-keys.com. If you are moving to the island for good, our Moving to Key West guide covers the wider picture.

Frequently asked questions

How far is Chicago from Key West?

Roughly 1,500 to 1,600 miles, depending on the exact starting address in the Chicago area.

Can the truck deliver to my Old Town house?

Sometimes, if the street has the width, turning room, and overhead clearance. If it does not, we will arrange a nearby corner or a larger lot, such as the old Sears center lot on North Roosevelt Boulevard.

Can you deliver onto NAS Key West?

Only if the driver has the required access, which is often not the case. We usually meet just off base and hand the car over to you or your sponsor.

Does one truck go from Chicago all the way to Key West?

Usually not. A trusted partner carrier runs the interstate leg. In-N-Out Keys handles the Key West delivery on its own truck.