Frontier AirlinesDepart07:00
Thu, Dec 17ORD → SAN
5h 33m · 1 stop
$85one way, per person
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- Cheapest fare
- $85
- Cheapest month
- December
- Direct flights
- Yes
- Flight time
- 4h 25m
Frontier Airlines · Thu, Dec 17
from $85
Southwest Airlines and Alaska Airlines
2,790 km
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Cheapest month to fly from Chicago to San Diego
Lowest one-way fare per person in each month. Choose a month to see every date.
Cheapest dates in December 2026
The lowest fares we've seen for each day, cheapest first.
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Where to stay, what to do and getting around, from our travel partners.
About flights from Chicago to San Diego
Chicago (CHI) and San Diego (SAN) are about 2,790 km apart. Direct flights take around 4h 25m, and recent direct fares were with Southwest Airlines and Alaska Airlines. Over the next few months, one-way fares start from $85, and December 2026 is currently the cheapest month to fly.
These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.
Frequently asked questions
How much is a flight from Chicago to San Diego?
The cheapest one-way fare we've seen recently is $85 with Frontier Airlines, departing Thursday, December 17, 2026. Over the coming months, the lowest fare in each month ranges from $85 to $134.
What is the cheapest month to fly from Chicago to San Diego?
December 2026 currently has the lowest fares, from $85 one way.
Are there direct flights from Chicago to San Diego?
Yes. Recent direct fares were with Southwest Airlines and Alaska Airlines.
How long is the flight from Chicago to San Diego?
A direct flight takes about 4h 25m. Chicago and San Diego are around 2,790 km apart.
Which airlines fly from Chicago to San Diego?
Recent fares on this route were with Southwest Airlines, Frontier Airlines and Alaska Airlines.
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