Planning a driveaway from Chicago to Florida
Last updated: July 27, 2026
A Chicago to Florida driveaway is about 1,200 miles to Tampa or Orlando and roughly 3 days. SelectDrive's illustrative day-rate model produces about $2,000 to $2,500 for a gas vehicle. This page is route planning information, not an offer of currently active interstate transportation.
Planning status as of July 27, 2026: SelectDrive is accepting route details for planning estimates only while its federal interstate operating authority is pending. No interstate for-hire move will start until the required operating authority is granted and active, and the specific trip has current insurance, vehicle, driver, and signed agreement approvals. A pet that travels well may accompany the vehicle it belongs to, and ordinary belongings that fit safely below the window line may be accommodated, but both require advance disclosure and written approval in the trip agreement. Approval is separate from the price estimate and is never automatic. These accommodations are incidental to delivering the vehicle. SelectDrive does not offer household goods moving, standalone goods delivery, or standalone pet transport. No person may ever travel in the vehicle.
The Chicago to Florida route
From the Chicago area, the drive south runs through Indiana, Kentucky, Tennessee, and Georgia into Florida. Tampa and Orlando are about 1,200 miles and roughly three days. Naples, Fort Myers, and Miami are 1,350 to 1,400 miles. SelectDrive is based in the Des Moines metro, about 330 miles west of Chicago, so a future written estimate would identify positioning travel to a Chicago-area pickup.
Planning cost for this lane
The table below is an illustrative Chicago to Tampa or Orlando planning worksheet at about 1,200 miles. It is not a quote or reservation. Any future written quote would use exact addresses and then-current approved terms.
Driver pay is $450 per day, billed in half-day increments with a one-day floor. A planning day is about 8 driving hours or roughly 500 miles. This gas-vehicle worksheet uses fuel at about $0.18 per mile, tolls at about $0.02 per mile, lodging at $120 per night, and an insurance surcharge at 8 percent of driver pay.
| Driver pay (2.5 days at $450 per day) | $1,125 |
| Gas fuel planning amount (1,200 mi at about $0.18 per mile) | $216 |
| Tolls planning amount (about $0.02 per mile) | $24 |
| Lodging planning amount (2 nights at $120) | $240 |
| Insurance surcharge (8 percent of driver pay) | $90 |
| Positioning, cheaper feasible round-trip drop-off or flight plus ground transport | Itemized from exact addresses |
| Illustrative gas-vehicle total | $2,000 to $2,500 |
Electric vehicle note: Charging is billed at documented actual cost with receipts, not the gas fuel planning amount shown above. The exact vehicle and battery affect highway range and trip duration, and an EV usually takes longer on the same route because of charging stops.
Planning estimate only. Naples, Fort Myers, and Miami are farther. No price or date is offered or reserved while interstate authority is pending. Plan another route.
Why driveaway for this lane
Chicago sends a large snowbird population to Florida every fall and back every spring. A future approved driveaway could let the customer fly while an assigned driver handles the car. Any pet or ordinary belongings would require advance written trip approval, and no person may ever travel in the vehicle. See snowbird car shipping planning and the honest driveaway vs driving it yourself breakdown.
Frequently asked questions
What is a planning estimate for a Chicago to Florida driveaway?
A Chicago to Tampa or Orlando route is about 1,200 miles. Under the day-rate model, an illustrative gas-vehicle total is about 2,000 to 2,500 USD, including route-specific positioning. Driver pay is 450 USD per day in half-day increments with a one-day floor. For an electric vehicle, charging is billed at documented actual cost with receipts instead of the gas fuel allowance. Naples, Fort Myers, and Miami are farther. This is not a booking quote, and interstate service is not active while required operating authority is pending.
How long does the Chicago to Florida drive take?
A planning schedule is about 3 days using about 8 driving hours or roughly 500 miles per day with overnight stops. Chicago to Tampa or Orlando is roughly 1,200 miles, and Naples or Miami is 1,350 to 1,400 miles. An electric vehicle may take longer because charging stops depend on the exact vehicle and battery.
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Considering a Chicago to Florida move?
Share route details for a nonbinding planning estimate. This does not reserve service or a date.