From the Chicago Loop, the North Shore, or the western suburbs, the drive to the Florida Keys is a long one: roughly 1,500 to 1,600 miles, depending on whether you are headed to Key Largo or all the way to Key West. That is two or three full days on I-65 or I-57, through Nashville or Atlanta traffic, the length of Florida, and then the Overseas Highway. Plenty of Chicago-area snowbirds would rather fly out of O’Hare or Midway and have the car waiting on the islands.
In-N-Out Keys LLC, operating out of Marathon at 9981 Overseas Hwy, Marathon, FL 33050, arranges this route regularly. A trusted, licensed partner carrier handles the long haul from Illinois to Florida. Our own truck and driver handle the Keys delivery, from MM 0 in Key West to MM 112 in Key Largo, and you work with one team from quote to drop-off.
At a glance
- Route: Chicago and the suburbs → anywhere in the Florida Keys (MM 0–112)
- Typical distance: Roughly 1,500–1,600 miles
- How it works: A trusted, licensed partner carrier runs the long haul to Florida; In-N-Out Keys’ own truck and driver handle the Keys leg down US-1
- Best booking window: Book early for October–December southbound and April–May northbound, and offer a pickup window of a few days
- Open vs enclosed: Open is the standard, more economical choice for daily drivers; enclosed suits classics, convertibles and high-value cars
This Chicago guide sits alongside our broader Midwest to Florida Keys car shipping overview, which also covers Ohio, Michigan, Indiana, Wisconsin, and Minnesota. If your destination is specifically Key West, see our Key West delivery page as well.
How the Chicago-to-Keys route is set up
Most moves from Chicagoland are done in two stages:
- A partner carrier we name before you book loads the vehicle in the Chicago area and brings it south to Florida.
- In-N-Out Keys takes the final leg down US-1, including the 18-Mile Stretch and, for Lower Keys and Key West deliveries, the Seven Mile Bridge.
Getting a car from Illinois to South Florida is a familiar interstate job. Getting it onto the islands is the part mainland companies often treat as an afterthought, sometimes asking you to meet a truck in Homestead or Florida City.
The last 100-plus miles run on a two-lane highway with bridges, speed zones, and weekend traffic. We plan that stretch from the start, because it is the work our Florida truck does every week.
| 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 the Chicago area, at your address or a nearby meet spot. | 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, for the Lower Keys and Key West, the Seven Mile Bridge. | 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 |
Where we pick up in the Chicago area
Common pickup areas include:
- The city of Chicago, when a safe loading spot is available
- North Shore communities such as Evanston, Wilmette, and Highland Park
- Western and southwestern suburbs including Naperville, Oak Brook, Downers Grove, and Orland Park
- Northwest suburbs near O’Hare, including Schaumburg, Arlington Heights, and Elk Grove Village
- Farther starts such as Aurora, Joliet, and Rockford
A full-size car hauler needs room to park and drop a ramp. Downtown streets, alley garages, and tight condo decks are often a poor fit. If that sounds like your building, we will usually suggest a nearby lot or a wide side street close to I-90, I-94, I-55, or I-80. That kind of meet is a normal Chicago pickup, and it often makes the day shorter.
Tell us about garage height limits, loading-dock rules, and HOA restrictions when you request a quote.
Snowbird timing from Chicago
The busy season on this corridor is familiar if you already winter in the Keys:
| When | Direction | What to know |
|---|---|---|
| October – December | Southbound | Busiest stretch for Chicago 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. |
November and December pickups can be slowed by early snow, ice, or holiday traffic around the airports. Booking with a pickup window of a few days, rather than a single date, gives us more room to place the car on the right truck.
If you already know your spring return dates, mention them when you book the trip down. For seasonal planning, see our seasonal auto shipping page.
Heading the other way later in the year? Auto Shipping Near Me publishes return-route pages for Key West to Chicago and Marathon to Chicago. We can help you plan the Keys pickup for the trip home.
Open or enclosed from Illinois
Open transport
- The standard choice for most daily drivers
- The more economical option
- Runs the whole route, including the Keys leg
Enclosed transport
- Worth a look for a classic, a convertible, or a freshly painted car
- Keeps the car off the winter road spray Midwestern cars collect
- Large enclosed trailers are not always practical on US-1, so some shipments finish the Keys leg on a smaller open trailer
We will explain the plan for your car before you book. Our open versus enclosed guide covers the tradeoffs.
What it costs
Price depends on the vehicle, your exact pickup and delivery addresses, the time of year, how flexible you can be, and whether you choose open or enclosed transport. Larger vehicles and a Key West or Lower Keys delivery can also affect the number.
We would rather quote your actual route than publish a one-size-fits-all number. See our cost guide for what moves the price, then request a quote with your ZIP codes and dates for the number that applies to your trip.
Delivery in the Keys
We deliver throughout the Florida Keys, MM 0 to MM 112, including Key Largo, Islamorada, Marathon, the Lower Keys, and Key West. Operating out of Marathon means the last-mile team is already on the islands.
What to have ready
- A reachable contact at pickup in Illinois and at delivery in the Keys
- Gate codes, condo rules, or marina and HOA instructions, if they apply
- A plan for tight streets. Many canal roads and Old Town Key West blocks cannot take a full-size hauler, so a nearby lot or a short meet is common and is arranged in advance.
- Daylight for the delivery inspection when you can arrange it
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
Our preparation guide walks through the rest.
How payment works
Most carriers accept COD, but fewer take billed payments, so paying on delivery lets us line up the best carrier for your route. A deposit may be collected when you book; your quote spells out what is due and when. See our pay on delivery page for details.
Get a quote for Chicago to the Keys
Share your pickup ZIP, the Keys delivery address, the vehicle, and a preferred window. Request a quote or call (754) 714-2439. You can also email tony@in-n-out-keys.com.
Frequently asked questions
How far is Chicago from the Florida Keys?
Roughly 1,500 to 1,600 miles, depending on whether you are delivering to the Upper Keys or all the way to Key West.
Does one truck go the whole way from Chicago?
Usually not. A trusted, licensed partner carrier runs the interstate leg. In-N-Out Keys handles the Florida Keys delivery on its own truck.
How long does Chicago to the Keys car shipping take?
Transit time depends on distance, the season, weather, and how the long-haul and Keys legs line up. We give you a realistic window for your job rather than a guaranteed number of days.
Can you deliver to a condo or gated community?
Often yes, or we will arrange a nearby meet if the truck cannot enter safely. Tell us about gates and tight streets when you book.
In-N-Out Keys LLC
USDOT 4120018 · MC 1583555
Operating out of Marathon
9981 Overseas Hwy, Marathon, FL 33050
Serving the entire Florida Keys, MM 0–112
