Chicago (MDW) to New Orleans (MSY) flights
One airline flies nonstop from Chicago (MDW) to New Orleans (MSY): Southwest Airlines. The two airports are 828 miles (1,332 km) apart. There are also 30 ways to fly it with one stop, through Saint Louis, Nashville and Louisville and more.
Airlines flying nonstop from MDW to MSY
- Southwest AirlinesNot in an allianceWho books it
MDW to MSY with one stop
30 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- 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)Southwest Airlines, then Allegiant Air
- Via Milwaukee (MKE)Southwest Airlines the whole way
- Via Knoxville (TYS)Allegiant Air, then American Airlines and Southwest Airlines
- 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)Southwest Airlines, then American Airlines
- Via Houston (HOU)Southwest Airlines the whole way
- Via Dallas (DFW)Frontier Airlines the whole way
- Via Savannah (SAV)Southwest Airlines, then Breeze Airways
MDW to MSY: common questions
Which airlines fly nonstop from MDW to MSY?
Southwest Airlines flies nonstop from Chicago (MDW) to New Orleans (MSY).
How far is Chicago from New Orleans by plane?
Chicago (MDW) and New Orleans (MSY) 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 MDW to MSY cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for MDW to MSY with taxes and fees.
Where can I connect between Chicago and New Orleans?
The most direct connections are through Saint Louis (STL), Nashville (BNA), Louisville (SDF), Cincinnati (CVG) and Milwaukee (MKE). 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.