Flying from Chicago to San Diego can be expensive. Our search helps you compare cheap flights, airfare deals, and flight tickets across airlines and agencies so you can book at the best price.
We scan trusted travel agencies and airline booking systems for the route Chicago - San Diego (CHI - SAN). We do not sell tickets or add fees - you choose where to buy.
Airfares vary by date, time, and airport. Use filters to find the best option by departure/arrival time, number of stops, airline or alliance, and booking channel.
If your dates are flexible, check the low-fare calendar to find the cheapest days. Booking round-trip in one order often reduces fees, and prices usually rise as departure approaches.
We also recommend you to look through the prices for return tickets from San Diego to Chicago.
Airfares found by our users in the past 24 hours
The price for these dates could change. Use search to get the best price.
Average round-trip airfares from Chicago to San Diego by months
| Month | Round-Trip |
|---|---|
| February 2026 | 10.02 - 14.02from £136 |
| March 2026 | 22.03 - 25.03from £142 |
| April 2026 | 03.04 - 02.05from £109 |
| May 2026 | 01.05 - 05.05from £105 |
| June 2026 | 05.06 - 13.06from £174 |
| July 2026 | find now |
| August 2026 | 10.08 - 17.08from £203 |
| September 2026 | find now |
| October 2026 | find now |
| November 2026 | find now |
| December 2026 | find now |
| January 2027 | find now |
Prices shown are based on searches from the last few days. Ticket prices can change and depend on availability at the time of booking.
Airlines are flying from Chicago to San Diego
| Southwest Airlines |
Popular flights from Chicago
Frequently asked questions about flights from Chicago to San Diego
How long does the flight from Chicago to San Diego take?
Flight duration from Chicago to San Diego varies by route, airline, and number of stops. Direct flights are faster. Use our search to compare options.
Are there direct flights from Chicago to San Diego?
Availability of direct flights from Chicago to San Diego depends on the route and season. Use the "Direct" filter in search to see only direct options.
Which airlines fly from Chicago to San Diego?
Several airlines operate flights from Chicago to San Diego. On this page you see airlines serving this route. Our search compares prices across airlines and agencies.
What is the cheapest month to fly from Chicago to San Diego?
Prices from Chicago to San Diego vary by month and demand. On this page you see average prices by month. Use the low-fare calendar and monthly table to find the cheapest dates.