New Orleans (MSY) to Chicago (MDW) flights
One airline flies nonstop from New Orleans (MSY) to Chicago (MDW): Southwest Airlines. The two airports are 828 miles (1,332 km) apart. There are also 31 ways to fly it with one stop, through Memphis, Saint Louis and Nashville and more.
Airlines flying nonstop from MSY to MDW
- Southwest AirlinesNot in an allianceWho books it
MSY to MDW with one stop
31 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Memphis (MEM)American Airlines, then Southwest Airlines
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Louisville (SDF)Southwest Airlines the whole way
- Via Cincinnati (CVG)Allegiant Air, then Southwest Airlines
- Via Milwaukee (MKE)Southwest Airlines the whole way
- Via Knoxville (TYS)American Airlines and Southwest Airlines, then Allegiant Air
- Via Atlanta (ATL)Delta Air Lines, Southwest Airlines and 1 more the whole way
- Via Kansas City (MCI)Southwest Airlines the whole way
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Cleveland (CLE)Southwest Airlines the whole way
- Via Dallas (DAL)Southwest Airlines the whole way
- Via Charlotte (CLT)American Airlines, then Southwest Airlines
- Via Houston (HOU)Southwest Airlines the whole way
- Via Dallas (DFW)Frontier Airlines the whole way
MSY to MDW: common questions
Which airlines fly nonstop from MSY to MDW?
Southwest Airlines flies nonstop from New Orleans (MSY) to Chicago (MDW).
How far is New Orleans from Chicago by plane?
New Orleans (MSY) and Chicago (MDW) are 828 miles (1,332 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does MSY to MDW cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for MSY to MDW with taxes and fees.
Where can I connect between New Orleans and Chicago?
The most direct connections are through Memphis (MEM), Saint Louis (STL), Nashville (BNA), Louisville (SDF) and Cincinnati (CVG). On 19 of them the same airline flies both flights, for example Southwest Airlines through Saint Louis.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.