San Diego to Chicago Car Shipping
San Diego to Chicago Car Shipping
Written by Richard Avery, President of Smart Auto Move · USDOT 2887232 · MC 969368
Shipping a car from San Diego to Chicago costs $1,225 to $1,375 on an open trailer. The trip is about 2,080 miles and takes five to seven days on the road. Trucks follow roughly the path of old Route 66, and we have staffed offices in Los Angeles and Chicago supporting both ends.
San Diego to Chicago car shipping prices
Running mid-size vehicle on an open trailer, reviewed September 2026. The other rows show the trip back and two related Southern California and Illinois lanes.
| Route | Distance | Days on the road | Open transport |
|---|---|---|---|
| San Diego to Chicago | 2,080 miles | 5 to 7 days | $1,225 to $1,375 |
| Rockford, IL to San Diego THE OTHER DIRECTION | 2,000 miles | 5 to 7 days | $1,200 to $1,350 |
| Chicago to Los Angeles FOR COMPARISON | 2,025 miles | 5 to 7 days | $1,225 to $1,375 |
| Sacramento to Chicago FOR COMPARISON | 2,050 miles | 5 to 7 days | $1,275 to $1,425 |
These are estimates, not fixed prices. Fuel is the largest cost in hauling a car and diesel prices change, so we review these ranges as the market moves. The days listed are time on the road, which starts once your pickup window ends. Enclosed runs about 80 percent more than open. For a car that will not start, add $200 or more for a winch truck. See how our national bands work.
Following old Route 66 in reverse
Route 66 once ran from Chicago to Santa Monica. The interstates that replaced it are the same roads a carrier takes from San Diego today.
The truck heads north on I-15 to Barstow and turns east on I-40, through Flagstaff, Albuquerque and Amarillo. At Oklahoma City it picks up I-44 to St. Louis, then I-55 carries it the last 300 miles into Chicago.
It is a busy freight corridor end to end, which keeps trucks moving in both directions. The one high point is Flagstaff, at about 7,000 feet. From December through March a snowstorm there can pause traffic for a few hours, so an extra day in your plan covers it.
San Diego to Chicago Car Shipping Questions
What customers moving a car from San Diego County to Chicagoland ask us most.
What does San Diego to Chicago car shipping cost?
Plan on $1,225 to $1,375 for a running mid-size car on an open trailer. That is door to door, from anywhere in San Diego County to anywhere in Chicagoland.
How long will it take?
Five to seven days on the road for about 2,080 miles. Your pickup window comes ahead of that, six days on Standard or three on Expedited.
Is Chicago to San Diego about the same price?
Very close. Our rate card has Rockford, Illinois to San Diego at $1,200 to $1,350. Illinois is an easy state to ship out of, so the trip west prices about the same as the trip east.
Which way do the trucks go?
Mostly along the path of old Route 66. Trucks take I-15 to Barstow, I-40 through Flagstaff, Albuquerque and Amarillo, then I-44 through Oklahoma City to St. Louis and I-55 up to Chicago.
Does winter matter on this route?
A little. I-40 climbs past Flagstaff at about 7,000 feet, where a snowstorm can hold trucks for a few hours. From December through March, give your plan an extra day.
When is the easiest time to book?
Spring and fall schedule most easily. June through August is the busy season, so book two to three weeks ahead then.
Do you move cars for Navy families?
Yes, often. San Diego is home to Naval Base San Diego, Coronado and Miramar, and Naval Station Great Lakes sits just north of Chicago. Share the earliest and latest dates your orders allow and we will fit the pickup inside them.
Is there a military discount?
Yes. Our military discount page explains who qualifies.
Where in San Diego County do you pick up?
Everywhere, including San Diego, La Jolla, Coronado, Chula Vista, National City, El Cajon, Escondido, Poway, Carlsbad, Encinitas and Oceanside.
Where around Chicago do you deliver?
The city and every suburb, including Evanston, Skokie, Oak Park, Schaumburg, Naperville, Aurora, Elgin and Joliet, plus North Chicago and Waukegan near Great Lakes.
Do you have offices on this route?
Yes, at both ends. Our Los Angeles office, at 5111 Harold Way, Suite 301, on 213-766-0064, supports Southern California. Our Chicago office is at 742 E 87th Pl, on 312-300-7773.
What if the truck can't reach my street?
Some older San Diego blocks downtown, and tight one-way streets in Chicago neighborhoods like Lincoln Park, are hard for a 75-foot hauler. The driver meets you at a nearby wide street or lot, at no charge.
How soon do I need to register in Illinois?
Within 30 days of moving in. Chicago residents also buy a city vehicle sticker.
Is door-to-door included?
Yes. It is part of every quote.
Open or enclosed?
Open fits nearly any daily driver. Enclosed is for a classic, a low sports car or new paint, and it keeps Midwest road salt off in winter. It costs about 80 percent more.
Can you ship a car that won't run?
Yes. It goes on a truck with a winch, usually for $200 or more above the running price.
What does Expedited get me?
A three-day pickup window instead of six. The drive takes the same time.
Can I send two cars?
Yes. Two cars going to one Chicago address can often ride together.
May I leave things inside the car?
Usually yes, within reason. Around 100 pounds in the trunk is fine. Carrier Cargo Insurance covers the car, not what you pack.
How do I prep my car?
Wash it, photograph all four sides, leave about a quarter tank, turn off the alarm and remove your FasTrak.
Who insures my car?
The carrier, through its Carrier Cargo Insurance, from loading in San Diego to delivery in Chicago. We email you the certificate when your truck is assigned.
How is my carrier picked?
We pick from our vetted network of over 16,000 carriers, all with active FMCSA authority and insurance on file.
How do I check you out?
Look up USDOT 2887232 or MC 969368 on SAFER, the free FMCSA website.
Does my car stay on one truck?
Yes. One truck and one driver carry it the whole way.
Should I drive it myself instead?
The drive is about 30 hours, or four days with stops. Shipping frees up those days and keeps 2,080 miles off your car.
Can my price change after I book?
It holds. Under the Smart Price Promise, the price we quote is the price you pay, as long as the car, route, condition and shipping details stay the same.
What do you need to quote me?
The two zip codes, your car's year, make and model, whether it runs, and when it is ready. Use the form above or call 888-709-9078.
From one Navy town to another
Naval Base San Diego is the Navy's largest base on the West Coast, and Coronado, Miramar and Camp Pendleton are all in the county too. Just above Chicago sits Naval Station Great Lakes, home of the Navy's boot camp.
That makes this a common lane for military families. Give us the earliest and latest dates your orders allow, and we fit the pickup inside that window. If the report date moves, one call to our Chicago office on 312-300-7773 moves your booking with it.
See our military discount before you book.
Pickup across San Diego County, delivery across Chicagoland
We collect from all over the county: San Diego, La Jolla, Coronado, Chula Vista, National City, El Cajon, Escondido, Poway, Carlsbad, Encinitas and Oceanside.
We deliver to Chicago and its suburbs: Evanston, Skokie, Oak Park, Schaumburg, Naperville, Aurora, Elgin, Joliet, and North Chicago and Waukegan near Great Lakes.
A few older streets downtown in San Diego, and the tight one-way blocks of Lincoln Park or Wicker Park in Chicago, are hard for a 75-foot hauler. The driver will meet you at a wider street or lot nearby, at no extra cost.
Illinois gives new residents 30 days to register a car, and Chicago residents also buy a city vehicle sticker. Our Chicago car shipping page covers the city in more detail.
Support at both ends of the trip
Our staffed Los Angeles office, at 5111 Harold Way, Suite 301, on 213-766-0064, supports Southern California pickups. Our staffed Chicago office is at 742 E 87th Pl, on 312-300-7773, close to your delivery.
Your car goes from your driveway straight onto the truck and stays there to Chicago. The offices are where your move is planned and tracked, and where someone picks up the phone in your own time zone.
Open, enclosed or expedited to Chicago
Open trailers carry most cars on this lane and cost the least. Enclosed suits a classic, a low sports car or fresh paint, and it keeps Midwest road salt off the finish, at about 80 percent more.
Expedited trims the pickup window to three days, useful when a lease or report date is fixed. Our open and enclosed guide covers the details.
Who carries and insures your car to Chicago
Your car rides with a carrier from our vetted network of over 16,000. All of them hold active FMCSA authority with insurance on file, and we check equipment and service history before assigning your car.
Carrier Cargo Insurance, the carrier's own policy, covers the car from loading in San Diego to delivery in Chicago, and your certificate arrives by email once the truck is set. On SAFER, you can look us up at USDOT 2887232, MC 969368.
What our customers report
Reviews from customers across our offices and service areas, Los Angeles and Chicago included. Read more on our BBB profile, where we hold an A+ rating and have been accredited since 2016.
Crystal Evans was very helpful.
More San Diego and Chicago car shipping pages
Related lanes and guides to read before you book.