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 14 253र |
| March 2026 | 22.03 - 25.03from 14 946र |
| April 2026 | 03.04 - 02.05from 11 468र |
| May 2026 | 01.05 - 05.05from 11 004र |
| June 2026 | 05.06 - 13.06from 18 236र |
| July 2026 | find now |
| August 2026 | 10.08 - 17.08from 21 306र |
| 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; connecting flights may take longer. Use our search to compare options and see exact durations for your dates.
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 our search and filter by "Direct" or "Non-stop" to see only direct options. We compare offers from many airlines and agencies.
Which airlines fly from Chicago to San Diego?
Several airlines may operate flights from Chicago to San Diego. On this page you can see airlines that serve this route. Our search compares prices across airlines and agencies so you can choose the best offer. We do not sell tickets; you book directly with the airline or agency.
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 can see average round-trip prices by month. Use the low-fare calendar and monthly table to find the cheapest dates. Booking in advance and avoiding peak seasons often helps get the best price.