Cheap flights from San Diego to Chicago from $163

If you don’t have specific dates for your trip between San Diego and Chicago, you can enter a date range into the departure and return fields. Most carriers on the Kiwi.com website allow you to search and book up to six months from the day of your search. Order the search results by the best, cheapest, or fastest route, or find the cheapest outbound and return combination in the pricing table.

Traveling between San Diego and Chicago, you can choose between direct (nonstop) flights or flights with one or more stops. You can select the number of stops on your journey, including an overnight stopover, and the duration of the stopover. What’s more, you can also select where you want to have your stopover. Want to say "Hi" to a friend in another city en route to your destination? Or fancy a quick round of shopping? Go Multi-City or Nomad and add places to your search that you wish to visit.

There are a number of airports in and around San Diego. The main one is San Diego International and other nearby airports include Tijuana International, John Wayne, Ontario International, Mexicali International, Hollywood Burbank, Palm Springs International, Imperial County, Long Beach, Hawthorne Municipal, Yuma International

There are a number of airports in and around Chicago. The main one is O Hare International and other nearby airports include Gerald R. Ford International, Dane County Regional, South Bend International, General Mitchell International, Fort Wayne International, Quad City International, General Wayne A. Downing Peoria International, Central Illinois Regional, Muskegon County, Kalamazoo/Battle Creek International.

This depends on the airline’s flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from San Diego, such as morning, afternoon, evening, or night, or select the exact hours for departure.

This depends on the airline’s flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Chicago, such as morning, afternoon, evening, or night, or select the exact hours for arrival.

This depends on the airline’s flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from San Diego, such as morning, afternoon, evening, or night, or select the exact hours for departure.

This depends on the airline’s flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Chicago, such as morning, afternoon, evening, or night, or select the exact hours for arrival.