Most shipments from Chicago to Naples take 3 to 5 days and cost $850 to $1,150 for open transport.
Updated May 2026
$850 to $1,150
Transit
3 to 5 days
Distance
1,395 miles
1,395 miles via I-65 / I-75. Pricing refreshed monthly based on current carrier rates.
Quotes well below the typical range are almost always bait. The broker holds your booking, then pumps up the price last minute when no carrier accepts the rate.
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 highest-volume snowbird corridors in the country. The route is a single straight shot south, down I-65 through Indianapolis, Louisville, and Nashville, picking up I-75 at Chattanooga and running the length of Florida to Naples. About 1,395 miles total. Most carriers run it in two driving days with overnight stops.
Snowbird season (October through March) is the heaviest demand window. Book three to four weeks ahead if you have a hard pickup date, since carrier supply tightens and prices climb 15 to 25%. Off-season runs from April through September can usually go on under a week of notice at slightly cheaper rates.
Most Chicago pickups happen at the home address. Suburban Chicago (Naperville, Schaumburg, Oak Park, Evanston) is straightforward. In dense city neighborhoods (Lincoln Park, Wicker Park, South Loop), the trailer cannot enter narrow residential streets, and we arrange a nearby meet point on the confirmation call after booking. In Naples, the carrier pool thins south of Fort Myers, and gated communities sometimes require meeting outside the gate.
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 $850 to $1,150 for open transport. Enclosed transport costs about 30 to 45% more. 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 1,395 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 30 to 45% 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.
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.
You can leave up to 100 pounds of personal items in one piece of luggage, placed in the trunk or cargo area. Some carriers will accept additional weight for an added fee; we can arrange this for you after booking.
Locked for 28 days. Nothing charged at booking.