Cheap Flights from San Diego (SAN) to Chicago (CHI)
Compare San Diego to Chicago flight deals
Find the cheapest month or even day of the year to fly to Chicago
Book the best Chicago fare with no extra fees
Flight deals from San Diego to Chicago
Looking for a cheap last-minute deal or the best round-trip flight from San Diego to Chicago? Find the lowest prices on one-way and round-trip tickets right here.Don’t miss a great deal
Stay one step ahead. Find the best value travel with the latest deals, tips and news.
Find the cheapest month to fly from San Diego to Chicago
We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like San Diego to Chicago flights are currently cheapest in May.Direct flights from San Diego to Chicago
Alternative San Diego to Chicago routes
Looking for the cheapest, fastest or easiest route from San Diego to Chicago? You could fly into the following airports instead.San Diego to Chicago: Flight information
The things to know before you go.| Cheapest flight found | $97 |
|---|---|
| Cheapest month to fly | May |
| Average flight time | 4 hrs, 4 mins |
| Most popular airline | Southwest Airlines |
| Average flights per week | 295 |
Finding cheap flights from San Diego to Chicago: Frequently asked questions
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
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
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?
Plan the rest of your trip from San Diego to Chicago
Prices shown on this page are estimated lowest prices only. Found in the last 45 days.
