Chicago (MDW) to New Orleans (MSY): 827 miles (1,331 km) great-circle, about 2h 10m nonstop by our estimate. Cheapest fare observed: $282 round-trip on Frontier, with 1 stop, departing May 10, 2026.
$282 round-trip, Frontier F92292, departing 2026-05-10 at 06:00, returning 2026-05-12. The recorded itinerary left on a Sunday, returning on a Tuesday 2 nights later; the fare was observed 15 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $282, it ranked 15th of the 30 round-trip fares we recorded from MDW (median $316). That is 34.1 cents per great-circle mile (round-trip price over one-way distance), above the MDW median of 22.1 cents across 30 round-trip routes.
Routes from MDW of similar length: New York (730 mi) at $211 and Houston (938 mi) at $253.
Frontier had the cheapest fare on 11 of 30 MDW routes. It is the 26th longest of the 30 routes we track from MDW.
Of 10 departure airports with a fare to New Orleans, Chicago (MDW) ranked 10th at $282. Lowest: $107 from Orlando (MCO); highest: $282 from Chicago (MDW); 5 nonstop. Cheapest-fare airlines (routes): Frontier (5), Spirit (3), airline MX (1) and Southwest (1).
Travelpayouts fares (cheapest per route, observed April 25, 2026); OurAirports coordinates and elevations; IANA zones America/Chicago, America/Chicago; flight time is our estimate.