Chicago Midway to Jacksonville (MDW → JAX). We are tracking 5 fares on this route.
Cheapest tracked fare $88 · typical price $156 · you save about $68 (44%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
—
2026-10-31
1 stop
$88
Frontier Airlines
2026-12-02
1 stop
$92
—
2026-11-06
1 stop
$108
Frontier Airlines
2026-11-27
1 stop
$119
Frontier Airlines
2026-10-24
1 stop
$124
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 Jacksonville get?
The cheapest fare we have tracked on this route is $88, compared with a typical $156 for a trip of this distance.
Is it cheaper to fly to Jacksonville 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 Jacksonville 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.