Chicago Midway to Honolulu (MDW → HNL). We are tracking 15 fares on this route.
Cheapest tracked fare $270 · typical price $590 · you save about $320 (54%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
Southwest Airlines
2026-10-24
1 stop
$270
Southwest Airlines
2026-12-01
1 stop
$300
Southwest Airlines
2026-10-14
1 stop
$311
Southwest Airlines
2026-10-13
2 stops
$321
Southwest Airlines
2026-09-29
1 stop
$322
Southwest Airlines
2026-10-16
1 stop
$331
Southwest Airlines
2026-10-23
2 stops
$333
Southwest Airlines
2026-10-15
1 stop
$351
Southwest Airlines
2026-10-22
1 stop
$357
Southwest Airlines
2026-10-12
2 stops
$363
Southwest Airlines
2026-09-16
1 stop
$387
Southwest Airlines
2026-09-09
1 stop
$387
Southwest Airlines
2027-01-03
1 stop
$393
Southwest Airlines
2026-09-17
1 stop
$393
Southwest Airlines
2026-10-10
2 stops
$479
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 Honolulu get?
The cheapest fare we have tracked on this route is $270, compared with a typical $590 for a trip of this distance.
Is it cheaper to fly to Honolulu 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 Honolulu 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.