Cheap flights from San Diego to Chicago (All Airports)
San Diego to Chicago (All Airports) (SAN → CHI). We are tracking 5 fares on this route.
Cheapest tracked fare $81 · typical price $199 · you save about $118 (59%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
—
2026-11-04
1 stop
$81
—
2026-10-03
1 stop
$120
—
2026-10-24
1 stop
$124
—
2026-10-23
1 stop
$139
—
2027-06-04
Direct
$153
Could you save more?
The airport you were going to fly from is often not the cheapest one. Compare every airport in a region against each other, or check whether a multi-day stopover beats the direct fare.
How cheap can flights from San Diego to Chicago (All Airports) get?
The cheapest fare we have tracked on this route is $81, compared with a typical $199 for a trip of this distance.
Is it cheaper to fly to Chicago (All Airports) from a different airport?
Often, yes. Fares out of secondary airports are frequently cheaper than the obvious hub, but they are the ones most likely to be missing from a normal search. Our reverse search compares every airport in a region against each other so the cheaper departure point is not hidden.
Could a stopover make San Diego to Chicago (All Airports) cheaper?
Sometimes. On thin long-haul routes a two-leg trip with a multi-day stopover can beat the direct fare, and occasionally a direct fare is not sold at all. Our detour search prices those routings against the direct flight.