Cheap flights from San Diego to Chicago
Fares from $135 in November 2026. Compare every month below, then book with the site you like.
Search San Diego → Chicago flightsCheapest San Diego to Chicago fares by month
Lowest price per person found in recent searches. Prices change often and are checked when you book.
- November 2026Nov 5 · one way · Alaska Airlines · Direct$135See deal
San Diego to Chicago at a glance
- Distance1,720 miles
- Nonstop flight timeabout 4h 15m
- Cheapest monthNovember 2026
- Airport codesSAN → CHI
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Frequently asked questions
- How much is a flight from San Diego to Chicago?
- The cheapest fare we found recently is $135 per person, departing Nov 5 on Alaska Airlines. Prices change daily, so search your dates to see today's fares.
- What is the cheapest month to fly from San Diego to Chicago?
- November 2026 is currently the cheapest month, from $135.
- Are there direct flights from San Diego to Chicago?
- Yes. Recent searches found nonstop fares from $135.
- Which airlines fly from San Diego to Chicago?
- The cheapest recent fares on this route were on Alaska Airlines.
- How long is the flight from San Diego to Chicago?
- San Diego and Chicago 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 San Diego to Chicago?
- 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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