Detour Flights

Cheap flights from Chicago Midway

We are tracking 344 fares out of Chicago Midway (MDW) to 135 destinations.

Cheapest tracked fare $52  ·  about $31 below the typical price for that distance

Cheapest fares we're tracking

ToDepartsStopsPrice
St Louis (STL)2026-10-31Direct$52
Minneapolis (MSP)2026-10-24Direct$53
Minneapolis (MSP)2026-10-27Direct$53
(STL)2026-10-15Direct$54
St Louis (STL)2026-11-07Direct$56
St Louis (STL)2026-12-21Direct$57
Atlanta (ATL)2026-11-15Direct$60
Atlanta (ATL)2026-12-10Direct$60
(CLE)2026-10-20Direct$62
Atlanta (ATL)2026-11-13Direct$63
(FLL)2026-12-14Direct$65
Orlando (MCO)2026-12-22Direct$68
(ORL)2026-12-21Direct$69
(HOU)2026-11-041 stop$69
Houston Intercontinental (IAH)2026-11-041 stop$69
(ORL)2026-12-22Direct$70
Orlando (MCO)2026-12-21Direct$70
(DFW)2026-10-281 stop$74
(LAX)2026-11-101 stop$75
Orlando (MCO)2027-01-121 stop$75

Popular destinations

Flights to St LouisFlights to MinneapolisFlights to AtlantaFlights to ClevelandFlights to Fort LauderdaleFlights to OrlandoFlights to ORLFlights to Houston HobbyFlights to Houston IntercontinentalFlights to Dallas-Fort WorthFlights to Los AngelesFlights to MiamiFlights to Washington DC (All Airports)Flights to BaltimoreFlights to Washington DullesFlights to JacksonvilleFlights to Washington ReaganFlights to BostonFlights to Las VegasFlights to New York LaGuardia

Compare every airport, not just this one

Pin one end of your trip and let a whole region compete for the other. The cheapest airport is often not the one you were going to use.

Find my cheapest airport

Common questions

Where can I fly cheaply from Chicago Midway?
We are currently tracking 344 fares out of Chicago Midway across 135 destinations, listed cheapest first above.
Is Chicago Midway the cheapest airport for this trip?
Not always. Cached fare feeds cover big hubs densely and secondary airports sparsely, so a cheaper nearby airport is often simply missing from a normal search rather than more expensive. Our reverse search prices a whole region's airports against each other to surface it.