Cheap flights from Chicago Midway to Milan Malpensa
Chicago Midway to Milan Malpensa (MDW → MXP). We are tracking 5 fares on this route.
Cheapest tracked fare $345 · typical price $622 · you save about $277 (44%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
Porter Airlines
2026-09-23
2 stops
$345
Porter Airlines
2026-09-26
2 stops
$366
Porter Airlines
2026-09-20
2 stops
$367
Frontier Airlines
2026-10-21
3 stops
$370
Porter Airlines
2026-09-19
3 stops
$390
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 Milan Malpensa get?
The cheapest fare we have tracked on this route is $345, compared with a typical $622 for a trip of this distance.
Is it cheaper to fly to Milan Malpensa 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 Milan Malpensa 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.