Cheap flights from Chicago to San Diego
Fares from $85 in December 2026. Compare every month below, then book with the site you like.
Search Chicago → San Diego flightsCheapest Chicago to San Diego fares by month
Lowest price per person found in recent searches. Prices change often and are checked when you book.
- November 2026Nov 17 · one way · Southwest · Direct$134See deal
- December 2026Dec 17 · one way · Frontier · 1 stop$85See deal
Chicago to San Diego at a glance
- Distance1,720 miles
- Nonstop flight timeabout 4h 15m
- Cheapest monthDecember 2026
- Airport codesCHI → SAN
Plan your San Diego trip
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Frequently asked questions
- How much is a flight from Chicago to San Diego?
- The cheapest fare we found recently is $85 per person, departing Dec 17 on Frontier. Prices change daily, so search your dates to see today's fares.
- What is the cheapest month to fly from Chicago to San Diego?
- December 2026 is currently the cheapest month, from $85. November 2026 is the most expensive, from $134.
- Are there direct flights from Chicago to San Diego?
- Yes. Recent searches found nonstop fares from $134.
- Which airlines fly from Chicago to San Diego?
- The cheapest recent fares on this route were on Southwest, Frontier.
- How long is the flight from Chicago to San Diego?
- Chicago and San Diego are about 1,720 miles apart, so a nonstop flight takes roughly 4h 15m. Flights with a stop take longer, depending on the connection.
- How do I find the cheapest flight from Chicago to San Diego?
- Search your dates on Gotoesy. We list fares from several booking sites sorted cheapest first, show nearby dates when your day has no saved fare, and send you straight to the seller to book.
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