Chicago Midway to Orlando (MDW → MCO). We are tracking 5 fares on this route.
Cheapest tracked fare $123 · typical price $164 · you save about $41 (25%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
Southwest Airlines
2026-09-16
Direct
$123
Frontier Airlines
2026-09-09
1 stop
$125
Southwest Airlines
2026-10-21
1 stop
$127
Frontier Airlines
2026-09-11
1 stop
$129
Frontier Airlines
2026-11-14
1 stop
$135
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 Chicago Midway to Orlando get?
The cheapest fare we have tracked on this route is $123, compared with a typical $164 for a trip of this distance.
Is it cheaper to fly to Orlando 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 Chicago Midway to Orlando 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.