Oakland to Chicago Midway (OAK → MDW). We are tracking 6 fares on this route.
Cheapest tracked fare $135 · typical price $244 · you save about $109 (45%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
Southwest Airlines
2026-10-27
Direct
$135
Southwest Airlines
2026-11-02
Direct
$135
Southwest Airlines
2026-10-21
1 stop
$152
Southwest Airlines
2026-10-22
1 stop
$157
Southwest Airlines
2026-11-08
Direct
$177
Southwest Airlines
2026-10-04
Direct
$180
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 Oakland to Chicago Midway get?
The cheapest fare we have tracked on this route is $135, compared with a typical $244 for a trip of this distance.
Is it cheaper to fly to Chicago Midway 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 Oakland to Chicago Midway 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.