Most shipments from Chicago to Naples take 3 to 5 days and cost $1,000 to $1,250 for open transport.
Updated August 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.
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Locked for 28 days. Nothing charged at booking.
Chicago to Naples is one of the busiest snowbird corridors in the country, and the route is simple: I-65 south through Indianapolis, Louisville and Nashville, then I-75 from Chattanooga down the length of Florida. About 1,331 miles. Most carriers cover it in two driving days with an overnight in between, which makes the transit itself predictable. What moves this lane around is the season, not the road.
Snowbird season runs October through March, and prices climb 15 to 25% in the peak weeks because everyone is heading the same direction at once. That is the whole mechanism: a carrier can fill a southbound trailer without trying, so there is no reason to discount it. Book three to four weeks out if your pickup date falls in that stretch, and from April through September a week of notice is usually enough. Summer is just cheaper.
Chicago is the easy half of this lane. Carrier supply is dense enough that dispatch usually happens within a couple of days of booking, and the only wrinkle is the older city neighborhoods, where the truck meets you a few streets away instead of at the door.
Naples is the harder half. The carrier pool thins south of Fort Myers, so the last stretch takes more arranging than the 1,200 miles before it, and gated communities on this end often mean meeting the driver at the entrance. We confirm the spot before the driver is on the road.
Reviewed by Andrey Zhe, Sequoia founder.
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. Pricing varies with season and vehicle type.
Shipping a car from Chicago to Naples takes 3 to 5 days door to door. The route is roughly 1,331 miles down I-65 and I-75.
The Chicago to Naples corridor is busiest from October through March, when snowbirds head south. Prices climb 15 to 25% during peak weeks. Off-season runs from April through September are cheaper and easier to schedule.
Open transport is the standard choice for most vehicles. Enclosed transport costs 40 to 70% more and is appropriate for high-value vehicles, classics, low-clearance sports cars, and any car where weather exposure or road debris is a real concern.
Wash the car so its condition is easy to record, photograph it from each corner, and leave about a quarter tank of fuel. Take out anything above the 100 pound personal item allowance, and take your toll transponder such as FasTrak, E-ZPass or SunPass off the windshield, because toll gantries can read it while the car rides the truck. Have a working key ready for the driver.
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.
You can cancel for free up to 7 days before pickup. After that, the deposit is non-refundable.
Locked for 28 days. Nothing charged at booking.