Chicago Midway to Maui Kahului (MDW → OGG). We are tracking 5 fares on this route.
Cheapest tracked fare $333 · typical price $582 · you save about $249 (43%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
Southwest Airlines
2026-12-15
1 stop
$333
—
2026-09-16
1 stop
$349
Southwest Airlines
2026-09-18
1 stop
$376
Southwest Airlines
2026-09-19
1 stop
$412
Southwest Airlines
2026-10-12
2 stops
$428
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 Maui Kahului get?
The cheapest fare we have tracked on this route is $333, compared with a typical $582 for a trip of this distance.
Is it cheaper to fly to Maui Kahului 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 Maui Kahului 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.