Fly nonstop from New Orleans to Chicago-Midway for $110 roundtrip on Southwest Airlines through October. For those in Chi-town looking to visit the Big Easy, this fare also works in reverse at the same price.

Travel Availability

Travel is available on Tuesday, Wednesday from early May through the end of October. Summer travel dates scarce.

Searching Southwest, I found this price available departing New Orleans MSY on Wednesday, September 18, returning from Chicago MDW on Tuesday, September 24, 2019.


This fare includes a carry-on bag, a personal item, and two free checked bags.

Seat Assignments

Southwest has an open seating policy, which means there are no assigned seats and you'll get to choose your seat during boarding. The order of boarding is determined by the time of check-in so check-in exactly 24 hours before departure or pay for priority boarding for a better choice of seat.

Alternate Fares

American and United Airlines are matching this $109 roundtrip fare but to Chicago O'Hare (ORD) on select dates. If you are having trouble finding travel days that work for your schedule, try booking two separate one-way tickets amongst the airlines and create a custom itinerary.

Related: How to Fly Southwest Airlines (And Get the Seat You Want)

See our fare details for booking info.

Looking for a place to stay in the Windy City? Here's what's available for the above dates on Hotelwatchdog.

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