Orlando to Chicago
Door-to-door vehicle transport from Orlando, FL to Chicago, IL. Central Florida back home to Chicagoland up the I-75 and I-65 corridor — Illinois, Wisconsin, and Indiana residents head this way every spring. Open and enclosed carriers running daily with 3–5 day delivery. Moving Midwest vehicles home since 2007.
“Wintered at our place in The Villages, headed back to Naperville. Picked up Wednesday morning, delivered Sunday afternoon. Driver communicated the whole way and the price was exactly as quoted.”
At approximately 1,160 miles via I-75 North and I-65, the Orlando to Chicago corridor is Central Florida’s main Midwest return lane. Carriers run this route daily from late February through June with steady year-round demand from relocations, students returning to Northwestern and U of Chicago, and seasonal residents of The Villages and Winter Park heading back to Chicagoland.
Pickup anywhere in Central Florida — Orlando, Winter Park, Lake Mary, Sanford, Kissimmee, Altamonte Springs, Clermont, plus The Villages. Standard window: 1–3 business days.
First major waypoint heading north on I-75. Carriers often pick up additional Southeast vehicles here before pushing on toward Tennessee.
Mid-route waypoint through Tennessee. Carriers transition from I-75 to I-65 in this stretch, with reliable rest and fuel stops.
Final stretch up I-65 through Kentucky and Indiana. Most carriers overnight near Indianapolis before the final push to Chicagoland.
Delivery throughout Chicagoland — Chicago, Naperville, Evanston, Schaumburg, Oak Park, Aurora, plus surrounding suburbs and college campuses.
We pick up at your Central Florida address and deliver to your Chicagoland destination. No terminals, no extra driving.
Every vehicle is covered by cargo insurance from pickup to delivery. FMCSA-licensed and fully bonded.
Track your vehicle 24/7. Know exactly where your car is at every step.
Midwest return lanes are core territory. We coordinate daily pickups across Central FL from late February to June.
No hidden fees. The price we quote is the price you pay. Open carriers from $825, enclosed from $1,275.
All prices are all-inclusive. No fuel surcharges, no terminal fees. Final quote depends on vehicle size and exact addresses. Spring snowbird return season (March–June) may add 10–20% due to peak northbound demand.
- Standard open trailer transport
- Full cargo insurance included
- Door-to-door pickup & delivery
- GPS tracking included
- 3–5 day transit time
- No upfront payment required
- Fully enclosed — weather protected
- Ideal for luxury, classic & exotic cars
- Enhanced cargo insurance coverage
- Door-to-door pickup & delivery
- GPS tracking included
- Priority scheduling available
- Pickup within 24–48 hours
- Priority route assignment
- Open or enclosed available
- Full cargo insurance included
- Dedicated transport coordinator
- Ideal for last-minute moves
From The Villages snowbirds to Northwestern relocations, Central Florida residents trust us to find the right carrier on the I-75 / I-65 northbound lane.
“Wintered at our place in The Villages, headed back to Naperville. Picked up Wednesday morning, delivered Sunday afternoon. Driver communicated the whole way and the price was exactly as quoted.”
“Son finished spring quarter at Northwestern and we needed his car shipped back from Winter Park. Four days door-to-door, no hassle, very professional. Made the end-of-year move stress-free.”
“Shipped my Corvette enclosed from Clermont up to Oak Park. Carrier knew what he was doing — covered, strapped, photo-documented at pickup. Showed up exactly when promised, no scratches.”
Everything you need to know about shipping your car on this route.
We service all surrounding cities — not just Orlando and Chicago. Door-to-door to any address along the full I-75 / I-65 corridor.
- Winter Park, FLPickup Available
- Lake Mary, FLPickup Available
- Kissimmee, FLPickup Available
- Sanford, FLPickup Available
- The Villages, FLPickup Available
- Clermont, FLPickup Available
- Naperville, ILDelivery Available
- Evanston, ILDelivery Available
- Schaumburg, ILDelivery Available
- Oak Park, ILDelivery Available
- Aurora, ILDelivery Available
- Joliet, ILDelivery Available
Chicago?
Book early — March through June is peak northbound demand. Real specialist responds within the hour.
Ship?
Tell us about your vehicle and route. A real transport specialist will respond within the hour with carrier options and pricing.
Response within 1 hour. No obligation, no upfront payment.
Need city-specific service? Visit our reverse-route page, partner sites, and nearby snowbird lanes covering the full I-75 / I-65 corridor.