Flights from New Orleans (MSY) to Chicago (MDW)

Route intelligence for MSY → MDW: direct flights, stopover options, and timetable coverage in one place.

Show route on mapAll flights from MSYAll flights to MDW

Direct flights

1 direct option(s) across 1 airline(s) · 1,330 km route distance.

  • Southwest Airlines · 135 min · 1330 km

Explore these airlines on this city pair

Open each airline route-map page to compare broader network depth before committing to a nonstop or one-stop strategy.

Southwest Airlines route map →

Stopover options

  • 1 stop(s) · 4h 5m · MSY → MDW
  • 1 stop(s) · 4h 15m · MSY → MDW
  • 1 stop(s) · 5h 35m · MSY → MDW
  • 1 stop(s) · 5h 36m · MSY → MDW
  • 1 stop(s) · 5h 36m · MSY → MDW
  • 1 stop(s) · 5h 39m · MSY → MDW
  • 1 stop(s) · 5h 39m · MSY → MDW
  • 1 stop(s) · 5h 40m · MSY → MDW
  • 1 stop(s) · 5h 40m · MSY → MDW
  • 1 stop(s) · 5h 40m · MSY → MDW
  • 1 stop(s) · 5h 40m · MSY → MDW
  • 1 stop(s) · 5h 40m · MSY → MDW

Timetable coverage

Published flight numbers: WN1585, WN1157, WN2357, WN2361, WN562

Flight number: WN 1585

Operating days: 2, 3

  • MSY 07:25 → MDW 09:40

Plan this city pair

Compare nearby alternatives and airline networks to decide whether a direct trip, one-stop connection, or reverse search gives you better options.

Explore all departures from MSY →Explore all arrivals to MDW →Compare airline network coverage →Browse airports by country →

Route planning checklist

  • Compare direct duration with one-stop total duration before committing to a fare.
  • Check inbound alternatives on flights to MDW when return timing is important.
  • Use Guides for alliance and hub strategy playbooks.
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