Chicago Midway to Honolulu (MDW → HNL). We are tracking 9 fares on this route.
Cheapest tracked fare $248 · typical price $410 · you save about $162 (40%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
—
2027-02-01
1 stop
$248
Southwest Airlines
2026-11-01
1 stop
$295
Southwest Airlines
2026-11-15
1 stop
$308
Southwest Airlines
2026-11-12
1 stop
$321
Southwest Airlines
2027-03-31
1 stop
$328
Southwest Airlines
2026-10-31
1 stop
$330
Southwest Airlines
2026-12-05
1 stop
$330
Southwest Airlines
2027-01-08
1 stop
$360
Southwest Airlines
2027-02-12
1 stop
$366
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 $248, compared with a typical $410 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.