San Jose to Chicago car shipping is $1,350 for a mid-size car on an open trailer, covering 2,140 miles in about 5 days. The same rate applies coming back from Chicago. Bigger vehicles, a single fixed pickup day, or a tight address at either end will push it higher. Enclosed trailers, non-running cars and oversized trucks are priced per vehicle.

About 5 days on the road once your car is collected, covering 2,140 miles. Pickup happens inside the date range you give us, so plan on a few extra days from booking to delivery. Federal hours-of-service rules limit how long a driver can be behind the wheel each day, which sets a practical floor on transit for a trip this length.

Your car picks up I-80 and stays on it through Reno, Salt Lake City, Cheyenne, Omaha and Des Moines before crossing into Illinois. I-80 runs from San Francisco to the edge of New York City, so this lane rides its western two thirds — one road, almost no turns.

One thing worth knowing about the northern route: I-80 crosses Donner Pass in the Sierra and the high plains of Wyoming, and both close to high-profile vehicles in winter storms. It rarely stops a shipment, but between December and March it can add a day. Give us a wider collection window in those months and it stops mattering.

San Jose was orchard country until the 1950s — it was known as the Valley of Heart's Delight before it was Silicon Valley — and it was rebuilt wide. Sunnyvale, Santa Clara, Cupertino and Milpitas load at the curb almost everywhere. The older streets in Willow Glen and the Rose Garden are tighter, so we sometimes meet a block or two away.

Usually, yes. The suburbs are straightforward — Naperville is 30 miles out and a full carrier reaches most driveways there. It gets harder in the Loop, and on the narrow one-way blocks of Lincoln Park, Wicker Park and Old Town, where there is little turning room. In those cases we meet you at a nearby wider street or lot, at no extra charge. Scheduling also works around traffic on the Kennedy, Dan Ryan, Eisenhower and Stevenson.

No. Your car never sits anywhere. It goes from your address straight onto the carrier and stays covered under Carrier Cargo Insurance for the entire trip. Our offices are where dispatchers book your transport and call you with updates, not storage yards. Fewer people handle your vehicle and there is no gap in coverage between pickup and delivery.

Open is what most cars travel on and what the price on this page is based on. It is the same kind of trailer that delivers new cars to dealerships. Enclosed puts your car inside, away from road spray and debris, and is usually chosen for luxury, classic, exotic or freshly painted cars. We price enclosed per vehicle rather than publishing a figure, because the difference varies by car and season.

Yes, as long as the carrier has a winch or the right equipment. Non-running cars are priced separately from the rate on this page. Tell us the true condition when you ask for a quote and the right truck turns up first time, with your price unchanged.

No. Asking for a San Jose to Chicago car shipping quote does not put you on a call list. We only use what you give us to answer you directly, and we never sell it to anyone. You are welcome to call us, though, on 213-766-0064 in California or 312-300-7773 in Chicago.