Chicago to Arizona and Florida Car Shipping: Illinois Snowbirds' Guide

When the first hard freeze hits Chicago, many Illinois residents start counting the days until they head somewhere warm. Most choose one of two destinations: the Arizona desert or the Florida coast. Either way, the drive is long, and it's not much fun in November weather. Shipping your car door-to-door lets you fly down, settle in and have your own car waiting for the season.

Two favorite winter destinations

Arizona. Phoenix, Scottsdale, Mesa, Sun City and Tucson draw Midwest snowbirds who want dry heat, golf and mountain views. Illinois to Arizona car shipping typically runs west along I-80 or I-44 and I-40 across the Plains.

Florida. Orlando, Tampa, Sarasota, Fort Myers, Naples and the Atlantic coast are long-time favorites. Chicago to Florida car shipping usually runs south through Indiana, Kentucky, Tennessee and Georgia on I-65 and I-75.

Both are well-traveled snowbird lanes. For destination-specific tips, see our snowbird car shipping to Arizona guide and our broader snowbird car shipping guide.

Chicago pickup tips

Chicago is a major carrier hub, which helps. A few local tips make pickup smoother:

• City streets and high-rises: Full-size carriers can't always reach narrow streets, alleys or downtown buildings. The driver may meet you at a nearby accessible spot, like a large store parking lot.
• Suburbs: Pickups in Naperville, Schaumburg, Oak Brook and the North Shore are common and usually straightforward.
• Winter weather: Snow and ice can affect pickup timing. Keep your driveway clear and your phone on.
• Downstate and rural Illinois: Fine to ship from, but allow a slightly wider pickup window.

Before pickup, wash the car so existing marks are easy to see, leave about a quarter tank of fuel and remove personal items. Your car's condition is recorded on the Bill of Lading (BOL) at pickup and checked again at delivery.

Transit expectations

These are typical ranges after pickup, not guarantees:

Peak snowbird demand, holiday schedules and winter storms along the route can widen these windows. We'll give you an estimate when you book and update you if anything changes.

Booking tips

• Book early. Fall is the busiest time of year on south- and west-bound snowbird lanes. Booking a few weeks ahead gives you more carrier options.
• Stay flexible. A pickup window of a few days often makes for a smoother match.
• Plan your return. If you'll head back to Illinois in spring, ask about booking the return trip early too, since spring is the reverse peak.
• Choose your transport type. Open transport is the most common and economical choice. Enclosed is worth considering for classic, luxury or low-clearance cars.