Most shipments from Chicago to Naples take 3 to 5 days and cost $1,000 to $1,250 for open transport.
Updated October 2026
$1,000 to $1,250
Transit
3 to 5 days
Distance
1,331 miles
1,331 miles via I-65 / I-75. .
Quotes well below the typical range are almost always bait-and-switch. You are quoted a low price to pay the deposit, and then the price is bumped at the last minute.
Insured under federal cargo liability requirements. Coverage is part of the quote, not an add-on.
Your quote is locked for 28 days. Cancel free up to 7 days before pickup.
Most shipments run door to door. If access is tight (narrow streets, low clearance), we will arrange a nearby meeting point.
One percent of every booking funds Clean Air Task Force, a nonprofit working on transport and energy emissions.
I'm really happy with the service!!! Fili is a really nice person and a professional.
It is a really professional company, and the service was great, and we also really value the environmental contributions they are doing. Thank you guys!! Will move my car again with you ❤️
Professional service and reasonable price considering they had to winch my car on the trailer.
.O1a0LCh8_1TgCAp.webp)
.BCBIJAen_ZbL0rP.webp)
.DToGaxuS_2h6UD8.webp)
.DV7dI2sG_KTQPG.webp)
.DLyL1g5U_ZCia4H.webp)
.CJ786qTl_ZfH9VB.webp)
.DYsVKq0W_ZHOnca.webp)
.D96_jjeg_ZofPe0.webp)
.ComJTPxM_9zjeq.webp)
Locked for 28 days. Nothing charged at booking.
Chicago to Naples is about 1,300 miles of interstate, south on I-65 from the edge of Chicago to Nashville and then down I-75 the rest of the way, which keeps the trip itself simple. The thought goes into the Naples end, where the city keeps big trucks off the streets nearest the Gulf, and into the car’s Illinois plates if it keeps them.
Most of the city lets a car carrier stop for long enough to unload, but the Gulf side doesn’t. Naples won’t let a tractor-trailer park on any public street west of Gordon Drive between Bay Road and 20th Avenue South, or west of Gulf Shore Boulevard from there up to the northern city limits, so a delivery to a house on the beach side of Gordon Drive or a building on Gulf Shore Boulevard is handed over quickly or on a street to the east. That’s why it helps to be there when the driver calls with the time, because the truck can’t sit and wait for you.
Not if Naples is where it now lives. Illinois tests most gasoline cars from the Chicago area every two years once they’re four years old, but a car that’s kept and mostly driven outside the testing area, in a place with no testing of its own, can be excused with an Out of Area Exemption, and Florida doesn’t test at all. So if the car is staying in Naples on its Illinois plates, apply for the exemption rather than planning a drive home for the test. A car that only spends the winter in Naples doesn’t fit that description, which means its test still falls due in the month its plates expire, and it’s worth checking which month that is before the car heads south.
Reviewed by Andrey Zhe, Sequoia founder.
If the move makes you a Florida resident, these are the state's rules for the car.
Checked September 2026 against Florida Statutes 320 and 627, U.S. EPA, Pinellas County Tax Collector. Rules change; the state's own site has the final word.
One percent of every booking goes to Clean Air Task Force, a nonprofit working on policy and technology to clean up transport and energy emissions.
Our giving is independently verified each year.
Shipping a car from Chicago to Naples costs $1,000 to $1,250 for open transport. Enclosed transport costs about 40 to 70% more, rising with distance. Your quote is locked for 28 days from the moment you book.
Shipping a car from Chicago to Naples takes an estimated 3 to 5 days door to door. The route is about 1,300 miles, down I-65 to Nashville, across to Chattanooga, then I-75 through Atlanta and most of the way down Florida.
Yes. Every toll, bridge and congestion charge the truck pays on the way is already in your quote, and nothing is added for them after you book.
You can cancel for free up to 7 days before pickup. After that, the deposit is non-refundable.
Nothing is charged at booking. The deposit is charged 7 days before your pickup window opens, and the remaining balance is paid to the driver at delivery.
Every shipment is insured by the carrier under federal cargo liability requirements.
One to two weeks ahead is enough on most routes. Busy corridors handle shorter notice, and quieter lanes benefit from the full two weeks. Booking earlier does not lower the price; it settles your dates sooner, and the quote is locked for 28 days either way.
Locked for 28 days. Nothing charged at booking.