American AirlinesDepart22:31
Sun, Jan 10SAN → ORD
4h 08m · Direct
$106one way, per person
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- Cheapest fare
- $106
- Cheapest month
- January
- Direct flights
- Yes
- Flight time
- 4h 08m
American Airlines · Sun, Jan 10
from $106
Alaska Airlines and American Airlines
2,790 km
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Cheapest month to fly from San Diego to Chicago
Lowest one-way fare per person in each month. Choose a month to see every date.
Cheapest dates in January 2027
The lowest fares we've seen for each day, cheapest first.
American Airlines
Frontier AirlinesDepart19:38
Sun, Jan 3SAN → ORD
5h 14m · 1 stop
$186one way, per person
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About flights from San Diego to Chicago
San Diego (SAN) and Chicago (CHI) are about 2,790 km apart. Direct flights take around 4h 08m, and recent direct fares were with Alaska Airlines and American Airlines. Over the next few months, one-way fares start from $106, and January 2027 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 San Diego to Chicago?
The cheapest one-way fare we've seen recently is $106 with American Airlines, departing Sunday, January 10, 2027. Over the coming months, the lowest fare in each month ranges from $106 to $135.
What is the cheapest month to fly from San Diego to Chicago?
January 2027 currently has the lowest fares, from $106 one way.
Are there direct flights from San Diego to Chicago?
Yes. Recent direct fares were with Alaska Airlines and American Airlines.
How long is the flight from San Diego to Chicago?
A direct flight takes about 4h 08m. San Diego and Chicago are around 2,790 km apart.
Which airlines fly from San Diego to Chicago?
Recent fares on this route were with Alaska Airlines, American Airlines and Frontier Airlines.
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