What’s the cost of a flight from San Diego to Chicago Midway?

Prices vary based on date, airline, and availability. Compare several options if you're flying between San Diego and Chicago.

Choose a date to explore the best fares now.

If possible, avoid holiday periods: ticket prices tend to rise quickly and availability drops, especially on busy routes. Morning and evening flights are often in high demand too — book early to get a good fare.

Which departure and arrival airports are available?

Between San Diego and Chicago, flight options may depend on the combination of airports available.

• Airports in San Diego: McClellan-Palomar is another departure point near San Diego - International.
• Airports in Chicago: Chicago is served by 3 airports - Midway, O'Hare, Rockford.

Sometimes flying into a nearby city can be more cost-effective. When a city has multiple airports, it’s worth comparing different flight combinations.

Adjust your flight filters for San Diego – Chicago Midway

Jetcost gives you tools to search smarter. Pick your ideal price range, airline, departure time, and flight type — then compare offers from the best travel agencies and carriers.

Other popular destinations

Planning a trip to United States? These cities are popular too: Atlanta, Los Angeles, Miami, New York City, Orlando.

Sorting options let you see the most affordable flights first. Some results may include extra fees shown only at checkout — always read carefully to see what’s included.