Detour Flights

Cheap flights from Chicago Midway

We are tracking 342 fares out of Chicago Midway (MDW) to 79 destinations.

Cheapest tracked fare $52  ·  about $44 below the typical price for that distance

Cheapest fares we're tracking

ToDepartsStopsPrice
Minneapolis (MSP)2026-11-10Direct$52
St Louis (STL)2026-10-31Direct$52
St Louis (STL)2026-09-30Direct$60
Atlanta (ATL)2026-09-09Direct$61
Atlanta (ATL)2026-09-06Direct$64
Atlanta (ATL)2026-09-11Direct$64
Minneapolis (MSP)2026-11-04Direct$77
Miami (MIA)2026-10-011 stop$81
Washington Reagan (DCA)2026-10-08Direct$81
Miami (MIA)2026-11-02Direct$83
Washington Dulles (IAD)2026-10-081 stop$83
Baltimore (BWI)2026-09-151 stop$85
Baltimore (BWI)2026-09-171 stop$85
Baltimore (BWI)2026-09-221 stop$85
Washington Reagan (DCA)2026-09-15Direct$85
Washington Reagan (DCA)2026-09-17Direct$85
Washington Reagan (DCA)2026-09-22Direct$85
Washington Reagan (DCA)2026-10-07Direct$85
Washington Dulles (IAD)2026-09-151 stop$85
Washington Dulles (IAD)2026-09-171 stop$85

Popular destinations

Flights to MinneapolisFlights to St LouisFlights to AtlantaFlights to MiamiFlights to Washington ReaganFlights to Washington DullesFlights to BaltimoreFlights to Toronto Billy BishopFlights to Fort LauderdaleFlights to Ontario CAFlights to Dallas-Fort WorthFlights to JacksonvilleFlights to San FranciscoFlights to Los AngelesFlights to PhoenixFlights to New York LaGuardiaFlights to AustinFlights to TampaFlights to New OrleansFlights to Las Vegas

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 342 fares out of Chicago Midway across 79 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.