New Orleans (MSY) to Chicago (MDW) · Nov 25, 2026 · return Dec 5, 2026

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Route overview: New Orleans to Chicago (MDW) flight deals

2026-11-25 → 2026-12-05 · Axel-exclusive $350.75

• Southwest Airlines WN3175: MSY 2026-11-25 10:10:00 → MDW 2026-11-25 12:30:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN2891 / WN393: MDW 2026-12-05 13:55:00 → MSY 2026-12-05 19:00:00; 1 stop(s) via AUS; 305 minutes. Local airport times.
  • WN2891: MDW 2026-12-05 13:55:00 → AUS 2026-12-05 16:35:00; layover at AUS: 65 minutes.
  • WN393: AUS 2026-12-05 17:40:00 → MSY 2026-12-05 19:00:00.

2026-11-25 → 2026-12-05 · Axel-exclusive $458.25

• Delta Air Lines DL1322 / DL1728: MSY 2026-11-25 10:10:00 → MDW 2026-11-25 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2026-11-25 10:10:00 → ATL 2026-11-25 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2026-11-25 15:25:00 → MDW 2026-11-25 16:18:00.
• Delta Air Lines DL4711 / DL1652: MDW 2026-12-05 09:30:00 → MSY 2026-12-05 16:16:00; 1 stop(s) via DTW; 406 minutes. Local airport times.
  • DL4711: MDW 2026-12-05 09:30:00 → DTW 2026-12-05 11:45:00; layover at DTW: 170 minutes.
  • DL1652: DTW 2026-12-05 14:35:00 → MSY 2026-12-05 16:16:00.

2026-11-25 → 2026-12-05 · Axel-exclusive $364.25

• Southwest Airlines WN103 / WN1536: MSY 2026-11-25 16:00:00 → MDW 2026-11-25 20:25:00; 1 stop(s) via ATL; 265 minutes. Local airport times.
  • WN103: MSY 2026-11-25 16:00:00 → ATL 2026-11-25 18:25:00; layover at ATL: 70 minutes.
  • WN1536: ATL 2026-11-25 19:35:00 → MDW 2026-11-25 20:25:00.
• Southwest Airlines WN2891 / WN393: MDW 2026-12-05 13:55:00 → MSY 2026-12-05 19:00:00; 1 stop(s) via AUS; 305 minutes. Local airport times.
  • WN2891: MDW 2026-12-05 13:55:00 → AUS 2026-12-05 16:35:00; layover at AUS: 65 minutes.
  • WN393: AUS 2026-12-05 17:40:00 → MSY 2026-12-05 19:00:00.

2026-11-25 → 2026-12-05 · Axel-exclusive $364.25

• Southwest Airlines WN4792 / WN287: MSY 2026-11-25 07:25:00 → MDW 2026-11-25 12:05:00; 1 stop(s) via STL; 280 minutes. Local airport times.
  • WN4792: MSY 2026-11-25 07:25:00 → STL 2026-11-25 09:10:00; layover at STL: 105 minutes.
  • WN287: STL 2026-11-25 10:55:00 → MDW 2026-11-25 12:05:00.
• Southwest Airlines WN2891 / WN393: MDW 2026-12-05 13:55:00 → MSY 2026-12-05 19:00:00; 1 stop(s) via AUS; 305 minutes. Local airport times.
  • WN2891: MDW 2026-12-05 13:55:00 → AUS 2026-12-05 16:35:00; layover at AUS: 65 minutes.
  • WN393: AUS 2026-12-05 17:40:00 → MSY 2026-12-05 19:00:00.

2026-11-25 → 2026-12-05 · Axel-exclusive $364.25

• Southwest Airlines WN4879 / WN651: MSY 2026-11-25 17:00:00 → MDW 2026-11-25 21:05:00; 1 stop(s) via BNA; 245 minutes. Local airport times.
  • WN4879: MSY 2026-11-25 17:00:00 → BNA 2026-11-25 18:30:00; layover at BNA: 60 minutes.
  • WN651: BNA 2026-11-25 19:30:00 → MDW 2026-11-25 21:05:00.
• Southwest Airlines WN2891 / WN393: MDW 2026-12-05 13:55:00 → MSY 2026-12-05 19:00:00; 1 stop(s) via AUS; 305 minutes. Local airport times.
  • WN2891: MDW 2026-12-05 13:55:00 → AUS 2026-12-05 16:35:00; layover at AUS: 65 minutes.
  • WN393: AUS 2026-12-05 17:40:00 → MSY 2026-12-05 19:00:00.

2026-11-25 → 2026-12-05 · Axel-exclusive $364.25

• Southwest Airlines WN3347 / WN2321: MSY 2026-11-25 15:15:00 → MDW 2026-11-25 20:35:00; 1 stop(s) via RDU; 320 minutes. Local airport times.
  • WN3347: MSY 2026-11-25 15:15:00 → RDU 2026-11-25 18:20:00; layover at RDU: 75 minutes.
  • WN2321: RDU 2026-11-25 19:35:00 → MDW 2026-11-25 20:35:00.
• Southwest Airlines WN2891 / WN393: MDW 2026-12-05 13:55:00 → MSY 2026-12-05 19:00:00; 1 stop(s) via AUS; 305 minutes. Local airport times.
  • WN2891: MDW 2026-12-05 13:55:00 → AUS 2026-12-05 16:35:00; layover at AUS: 65 minutes.
  • WN393: AUS 2026-12-05 17:40:00 → MSY 2026-12-05 19:00:00.

Explore this route

• All dates for this route
• Nov 24, 2026 · Return options
• Nov 26, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: New Orleans (MSY) to Chicago (MDW) · Nov 25, 2026 · return Dec 5, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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