Chicago Midway to Dubai (MDW → DXB). We are tracking 15 fares on this route.
Cheapest tracked fare $535 · typical price $924 · you save about $389 (42%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
Southwest Airlines
2026-09-19
2 stops
$535
Southwest Airlines
2026-10-11
2 stops
$540
Southwest Airlines
2026-10-02
2 stops
$547
Frontier Airlines
2026-09-10
3 stops
$561
Frontier Airlines
2026-10-30
3 stops
$574
Southwest Airlines
2026-10-09
2 stops
$581
Southwest Airlines
2026-09-11
2 stops
$608
Southwest Airlines
2026-10-10
2 stops
$620
Southwest Airlines
2026-11-16
2 stops
$623
Frontier Airlines
2026-10-22
3 stops
$627
Frontier Airlines
2026-10-07
3 stops
$664
Frontier Airlines
2026-10-08
3 stops
$666
Frontier Airlines
2026-09-18
3 stops
$692
Frontier Airlines
2026-10-17
3 stops
$708
Frontier Airlines
2026-09-13
3 stops
$712
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 Dubai get?
The cheapest fare we have tracked on this route is $535, compared with a typical $924 for a trip of this distance.
Is it cheaper to fly to Dubai 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 Dubai 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.