The Midwest's premier snowbird auto transport corridor. Chicago to Florida — door-to-door, fully insured, $0 upfront. Book early for winter season.
"Ship from Naperville to Naples every November. Lepke is the only company I use. Always on time, always perfect."
"Chicago to Fort Lauderdale in 4 days. Price was fair, driver was excellent. Saved me from driving in November weather."
"Retired to Sarasota from Schaumburg. Lepke handled my Cadillac with care. Highly recommend for any Midwest snowbird."
Chicago and the greater Chicagoland area send more snowbirds to Florida than almost any Midwest metro. Every winter, tens of thousands of Illinois residents — from downtown Chicago to Naperville, Schaumburg, and the surrounding suburbs — flee the brutal Midwest winters for Florida's warmth. And a large share of them ship their cars rather than drive 1,300+ miles each way. At Lepke Auto Transport, we've been managing this Chicago-to-Florida corridor since 1991 and understand its seasonal rhythms better than anyone.
The route typically runs south via I-65 or I-75 through Indiana, Kentucky, Tennessee, and Georgia before entering Florida. It's not quite as direct as the I-95 Eastern Seaboard route, but it's a well-established carrier lane with solid coverage. Transit time is 3–5 days depending on your pickup location in the Chicago metro and your Florida destination.
⚠️ Book before November: The Chicago-to-Florida corridor sees massive demand starting in late October and November. Chicagoans don't wait around when the first real cold front hits. Book your November, December, or January shipment in September or October to guarantee availability and competitive pricing. Last-minute bookings in November can mean waiting 1–2 weeks for a carrier.
Year-round demand: Beyond snowbird season, this corridor serves corporate relocations (Chicago has massive corporate headquarter activity), military families transferring, and retirees making permanent moves to Florida's Gulf Coast communities — The Villages, Sarasota, Naples, and Clearwater are all popular Midwest retiree destinations.
We pick up throughout the Chicago metro — from the city itself to Naperville, Schaumburg, Oak Park, Evanston, Joliet, Aurora, and all surrounding suburbs. Delivery covers all of Florida: Miami, Fort Lauderdale, Tampa, Sarasota, Naples, Orlando, Jacksonville, Clearwater, The Villages, and everywhere in between.
Before your vehicle ships, take a few minutes to prepare it properly. Remove all personal items, keep fuel under a quarter tank, and photograph your car from all sides. Our claims guide explains what to do if any issue arises, though with our vetted carrier network, the vast majority of shipments arrive without incident.
We serve all of Chicagoland — city neighborhoods, North Shore, western suburbs, and beyond.
Door-to-door delivery throughout Florida — Gulf Coast, Atlantic Coast, and Central Florida.
Typical open-transport pricing. Peak snowbird season (Nov–Jan) can add $100–$200 to base rates — book early to lock in better pricing.
| Route | Distance | Transit Time | Estimated Cost |
|---|---|---|---|
| Chicago → Miami | ~1,375 mi | 3–5 days | $1,000–$1,300 |
| Chicago → Tampa | ~1,285 mi | 3–5 days | $950–$1,250 |
| Chicago → Naples / Sarasota | ~1,295 mi | 3–5 days | $950–$1,250 |
| Naperville → Fort Lauderdale | ~1,365 mi | 3–5 days | $1,000–$1,250 |
| Schaumburg → Orlando | ~1,235 mi | 3–4 days | $930–$1,200 |
| Chicago → Jacksonville | ~1,100 mi | 3–4 days | $900–$1,150 |
| Chicago → The Villages | ~1,225 mi | 3–4 days | $930–$1,200 |
*Estimates for standard open-car transport. Enclosed transport, oversized vehicles, and inoperable cars are priced separately. See our peak season guide for timing advice.
We've managed the Chicago–Florida corridor for over 30 years. We know exactly when demand peaks and how to keep your shipment on schedule.
Your quote is your final price. No hidden fees, no bait-and-switch — especially important during peak snowbird season.
A dedicated rep manages your shipment from booking to delivery. Real people, not call centers.
Nothing due until a verified carrier is dispatched. Zero risk.
All carriers carry comprehensive cargo insurance. Your vehicle is protected throughout the journey.
Our massive network gives us options even when winter snowbird demand peaks in November.
Enter your Chicago-area pickup and Florida delivery — get a guaranteed price instantly.
A vetted carrier comes directly to your Chicagoland door. Joint inspection, ready to go south.
Your car arrives at your Florida address while you enjoy the warm weather.
Book in September or October for November, December, and January departures. The Chicago-to-Florida corridor is one of the busiest Midwest snowbird routes, and carrier demand surges in late October. Waiting until November means competing for limited slots, higher prices, and potential 1–2 week wait times. Early booking locks in better rates and guaranteed availability.
Yes — we serve all of Chicagoland. Naperville, Schaumburg, Aurora, Elgin, Joliet, Oak Park, Evanston, Downers Grove, Bolingbrook, and everywhere in between. Door-to-door pickup means we come to your home or condo complex — no need to drive to a terminal.
3–5 days once your vehicle is picked up. Chicago to Miami is typically 4–5 days; Chicago to Jacksonville can be 3–4 days. We provide a confirmed delivery window at booking. If you need it faster, ask about our expedited transport option.
Absolutely — and many of our customers do exactly that, year after year. We handle both the southbound run in fall/winter and the northbound return in spring. Once you're in our system, rebooking takes minutes. Many regular customers book both legs at once for the best planning and pricing.
Yes — all carriers in our network carry mandatory cargo insurance covering your vehicle throughout transport. Your own personal auto insurance remains in force as well, providing an additional layer of protection. The Bill of Lading signed at pickup documents your vehicle's condition so that any damage during transport is clearly attributable to the carrier. See our damage claims guide for full details.