Honolulu to Chicago Midway (HNL → MDW). We are tracking 14 fares on this route.
Cheapest tracked fare $247 · typical price $590 · you save about $343 (58%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
Southwest
2026-10-28
1 stop
$247
—
2026-11-04
1 stop
$247
—
2026-12-03
1 stop
$247
—
2027-01-13
1 stop
$247
—
2027-02-03
1 stop
$247
—
2026-10-21
1 stop
$247
—
2026-11-11
1 stop
$247
—
2027-01-20
1 stop
$247
Alaska Airlines
2026-10-08
2 stops
$278
Southwest Airlines
2026-11-16
1 stop
$301
Alaska Airlines
2026-09-12
1 stop
$333
Alaska Airlines
2026-10-10
1 stop
$378
Southwest Airlines
2026-10-17
1 stop
$392
Southwest Airlines
2026-12-19
1 stop
$401
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 Honolulu to Chicago Midway get?
The cheapest fare we have tracked on this route is $247, compared with a typical $590 for a trip of this distance.
Is it cheaper to fly to Chicago Midway 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 Honolulu to Chicago Midway 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.