Car shipping in Chicago

Chicago is one of the biggest sources of snowbird cars in the country. Every fall, retirees and part-year residents from the city and the suburbs send their cars to Florida's Gulf Coast or to Phoenix, Scottsdale and Tucson, then bring them back in spring. Between those migrations come relocations, students heading to and from the city's universities, and a lot of cars bought from suburban dealers.

For carriers, Chicago is a crossroads. I-65 runs south through Indianapolis toward Florida, and I-55 and I-44 point southwest toward Arizona. The city side is where it gets complicated: much of Chicago is laid out around alleys and permit parking, and it has winter parking rules that can turn a quick pickup into a tow-truck problem.

Pickup and delivery run throughout the city and across Cook, DuPage, Lake and the surrounding counties. Alleys, permit zones and tree cover vary block by block, so each area below comes with a note on how the handoff tends to go:

The biggest lane is Chicago to Florida, which runs I-65 to I-75 straight down to Tampa, Sarasota, Naples and Fort Myers, with plenty of cars going to Orlando and the Atlantic side too. A close second is Chicago to Arizona, the Midwest's other winter destination, with most cars going to the Phoenix area and the rest to Tucson.

If you're picking up from just over the line in Michigan or northwest Indiana, the Michigan to Florida lane follows a similar pattern down I-75. And for students heading to Northwestern, the University of Chicago, Loyola, DePaul or UIC, or going home after graduation, our college student car shipping page covers campus timing and who can sign.

A long car carrier can't turn into a Chicago alley, and it can't wait in a permit zone while someone looks for the keys. Here's how to set up a smooth pickup:

• Alley garages. If your garage opens onto an alley, bring the car around to the street in front of the house, or to the nearest wide street, at pickup time.
• Permit parking zones. The truck can stop to load but can't park for long. Have the car out and ready so the inspection and loading happen in one stop.
• Winter overnight parking ban. From December 1 through April 1, parking is banned on certain main streets between 3 and 7 a.m. Don't leave the car on one of those streets overnight waiting for an early pickup.
• Snow routes. When the city declares a two-inch snow ban, parking is banned on designated snow routes. Check the forecast the night before pickup in winter.
• High-rise pickups. In the Loop, Streeterville and River North, the car comes up from the garage to the street. Ask your building about loading-zone rules ahead of time.
• North Shore trees. Mature trees in Winnetka, Kenilworth and Lake Forest can hang low over side streets, so the driver may prefer to meet on Sheridan Road or Green Bay Road.

Most suburbs are simpler. A driveway in Naperville or Orland Park is usually fine, as long as your HOA allows a tractor-trailer on the street. Wherever the handoff happens, the driver inspects the car with you and records its condition on the bill of lading before loading.

Southbound demand out of Chicago builds in October and peaks in November and early December, as Midwest snowbirds get ahead of the first real snow. A car that needs to be in Florida or Arizona by late November should be booked in October, a month or more ahead. Flexibility on the pickup day helps more here than almost anywhere, because winter weather can push a truck back by a day.

The return runs from March through May. Spring is also road-construction season on the expressways and tollways, which can add time to city pickups, so a morning window is a good idea. Summer is the easiest time to schedule a relocation or a second car going south early. For the fall-and-spring pair booked as one plan, see snowbird car shipping.

The usual Chicago rhythm is to hand the car over first and get on a plane later in the week. The car covers the miles while you close up the house, and it reaches Florida or Arizona within a day or two of your own landing. Both airports have frequent flights to the major snowbird destinations: