Driveaway: drive my car from Chicago to Florida
Last updated: June 2026
A Chicago to Florida driveaway is about 1,200 miles to Tampa or Orlando and roughly 3 days, with a typical SelectDrive estimate of $1,900 to $2,500. Dan drives your car the whole way himself, with live GPS and photo inspection. It is the classic Midwest snowbird lane, and unlike a trailer carrier, your car can carry a pet and packed belongings.
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 Dan repositions to your Chicago-area pickup and that travel is included transparently in your quote rather than hidden in the per-mile rate.
What this lane typically costs
The table below works a Chicago to Tampa or Orlando move at about 1,200 miles. Your real number depends on the exact Florida city and your Chicago-area pickup address.
| Base rate (1,200 mi at $0.75) | $900 |
| Fuel | $215 |
| Tolls | $25 |
| Lodging | $240 |
| Insurance (8%) | $72 |
| Driver travel (to pickup and home) | $300 |
Estimate only. Naples, Fort Myers, and Miami run higher because they are 1,350 to 1,400 miles. Your real quote is calculated on your exact addresses. Estimate another route.
Why driveaway for this lane
Chicago sends a large snowbird population to Florida every fall and back every spring. Rather than make the long two-and-a-half-day drive yourself twice a year, you fly down and Dan delivers your car drive-ready, with the option to send a pet or a winter's worth of belongings along. See snowbird car shipping and the honest driveaway vs driving it yourself breakdown.
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