Cheap Flights from San Diego to Chicago in 2019

Flight information San Diego to Chicago

Cheapest roundtrip price last month


Non-stop airlines


Flights per week


Average flight time, total distance 1702 miles

3h 42min

Most popular airline last month


Chicago O'Hare International, Chicago Pal-Waukee, Chicago Dupage County, Chicago Midway and others

5 airports

San Diego To Chicago Flight Route

Who Offers This Route?

Many airlines fly from Chicago to San Diego, including Spirit Airlines, United Airlines, Delta, American Airlines, and Southwest Airlines. There are only a few departures each day, so be sure to check out the prices on Skyscanner to get the best deal.

What To Do While You Wait For Departure

The San Diego International Airport is a massive and high traffic airport that is fully loaded with amenities and activities to keep you busy before departure. You’ll be able to shop, eat, and even sleep while waiting for your departure.

There are three terminals at the San Diego International Airport, and for this route, you’ll be using Terminal 1. Terminal 1 is broken up into East and West halves and has 19 gates in total. Be sure to relax in one of the many lounge areas.

Are There Direct Flights?

There’s an even split between direct flights and flights with a layover on the San Diego to Chicago route. If you fly direct, the trip will take about four and a half hours. With a layover, most airlines estimate that the trip will take about twice as long.

Most layovers on this route are in smaller Midwestern airports and tend to last two hours.

Arriving in Chicago

Chicago is served by no fewer than four airports: Midway, O’Hare, Pal-Waukee, and Rockford. Most flights along this route arrive at O’Hare, although a sizeable minority arrive at Midway.


O’Hare is a massive airport that’s among the busiest in the world but is well-known for causing cancellations and delays. These delays tend to affect outbound traffic more than inbound traffic, but the landing pattern can vary from day to day.

O’Hare has four terminals, each of which has a couple of concourses. You’ll most likely be landing in Terminal 1. Once you’re on the ground, you’ll be able to hop on the subway system, grab a taxi, or take the bus quite easily.


Midway airport is closer to downtown Chicago, so you’ll still be able to hop on the subway or bus very easily. If you fly Southwest, there’s a good chance that you’ll be landing at Midway. Midway has three concourses and 43 gates. You’ll probably be landing at Concourse A.

In Chicago

Chicago is a massive city and has a lot of great infrastructure which will make moving from the airport to the downtown a breeze. Speaking of breezes, Chicago is commonly known as “the windy city,” so be sure to bring a jacket, even if you’re visiting in the spring.

Looking for hotels in Chicago?

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.