New Orleans (MSY) to Chicago (MDW), Dec 18–20, 2026: from $155 one way

New Orleans (MSY) to Chicago (MDW), Dec 18–20, 2026: from $155 one way on Axel, checked Oct 29, 2026. Lowest published fare: $155 one way, Axel-exclusive, Southwest Airlines, nonstop, Dec 18, 2026, 1 adult, economy, checked Oct 29, 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

2026-12-18 · one way · Axel-exclusive $155.00

• Southwest Airlines WN3174: MSY 2026-12-18 06:30:00 → MDW 2026-12-18 08:50:00; nonstop; 140 minutes. Local airport times.

2026-12-18 · one way · Axel-exclusive $220.00

• Delta Air Lines DL1322 / DL1728: MSY 2026-12-18 10:10:00 → MDW 2026-12-18 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2026-12-18 10:10:00 → ATL 2026-12-18 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2026-12-18 15:25:00 → MDW 2026-12-18 16:18:00.

2026-12-20 · one way · Axel-exclusive $201.50

• Southwest Airlines WN3174: MSY 2026-12-20 06:30:00 → MDW 2026-12-20 08:50:00; nonstop; 140 minutes. Local airport times.

2026-12-19 · one way · Axel-exclusive $201.50

• Southwest Airlines WN3174: MSY 2026-12-19 06:30:00 → MDW 2026-12-19 08:50:00; nonstop; 140 minutes. Local airport times.

2026-12-18 · one way · Axel-exclusive $155.00

• Southwest Airlines WN1899: MSY 2026-12-18 14:35:00 → MDW 2026-12-18 16:55:00; nonstop; 140 minutes. Local airport times.

2026-12-20 · one way · Axel-exclusive $201.50

• Southwest Airlines WN1899: MSY 2026-12-20 14:35:00 → MDW 2026-12-20 16:55:00; nonstop; 140 minutes. Local airport times.

2026-12-19 · one way · Axel-exclusive $201.50

• Southwest Airlines WN1899: MSY 2026-12-19 14:35:00 → MDW 2026-12-19 16:55:00; nonstop; 140 minutes. Local airport times.

2026-12-18 · one way · Axel-exclusive $165.00

• Southwest Airlines WN3121 / WN2694: MSY 2026-12-18 13:15:00 → MDW 2026-12-18 17:45:00; 1 stop(s) via MCI; 270 minutes. Local airport times.
  • WN3121: MSY 2026-12-18 13:15:00 → MCI 2026-12-18 15:15:00; layover at MCI: 65 minutes.
  • WN2694: MCI 2026-12-18 16:20:00 → MDW 2026-12-18 17:45:00.

2026-12-18 · one way · Axel-exclusive $165.00

• Southwest Airlines WN4879 / WN651: MSY 2026-12-18 17:00:00 → MDW 2026-12-18 21:05:00; 1 stop(s) via BNA; 245 minutes. Local airport times.
  • WN4879: MSY 2026-12-18 17:00:00 → BNA 2026-12-18 18:30:00; layover at BNA: 60 minutes.
  • WN651: BNA 2026-12-18 19:30:00 → MDW 2026-12-18 21:05:00.

2026-12-18 · one way · Axel-exclusive $165.00

• Southwest Airlines WN103 / WN1536: MSY 2026-12-18 16:00:00 → MDW 2026-12-18 20:25:00; 1 stop(s) via ATL; 265 minutes. Local airport times.
  • WN103: MSY 2026-12-18 16:00:00 → ATL 2026-12-18 18:25:00; layover at ATL: 70 minutes.
  • WN1536: ATL 2026-12-18 19:35:00 → MDW 2026-12-18 20:25:00.

2026-12-18 · one way · Axel-exclusive $165.00

• Southwest Airlines WN3347 / WN2321: MSY 2026-12-18 15:15:00 → MDW 2026-12-18 20:35:00; 1 stop(s) via RDU; 320 minutes. Local airport times.
  • WN3347: MSY 2026-12-18 15:15:00 → RDU 2026-12-18 18:20:00; layover at RDU: 75 minutes.
  • WN2321: RDU 2026-12-18 19:35:00 → MDW 2026-12-18 20:35:00.

2026-12-18 · one way · Axel-exclusive $165.00

• Southwest Airlines WN4792 / WN287: MSY 2026-12-18 07:25:00 → MDW 2026-12-18 12:05:00; 1 stop(s) via STL; 280 minutes. Local airport times.
  • WN4792: MSY 2026-12-18 07:25:00 → STL 2026-12-18 09:10:00; layover at STL: 105 minutes.
  • WN287: STL 2026-12-18 10:55:00 → MDW 2026-12-18 12:05:00.

2026-12-19 · one way · Axel-exclusive $214.50

• Southwest Airlines WN4879 / WN651: MSY 2026-12-19 17:00:00 → MDW 2026-12-19 21:05:00; 1 stop(s) via BNA; 245 minutes. Local airport times.
  • WN4879: MSY 2026-12-19 17:00:00 → BNA 2026-12-19 18:30:00; layover at BNA: 60 minutes.
  • WN651: BNA 2026-12-19 19:30:00 → MDW 2026-12-19 21:05:00.

2026-12-20 · one way · Axel-exclusive $214.50

• Southwest Airlines WN4792 / WN287: MSY 2026-12-20 07:25:00 → MDW 2026-12-20 12:05:00; 1 stop(s) via STL; 280 minutes. Local airport times.
  • WN4792: MSY 2026-12-20 07:25:00 → STL 2026-12-20 09:10:00; layover at STL: 105 minutes.
  • WN287: STL 2026-12-20 10:55:00 → MDW 2026-12-20 12:05:00.

2026-12-19 · one way · Axel-exclusive $214.50

• Southwest Airlines WN3121 / WN2694: MSY 2026-12-19 13:15:00 → MDW 2026-12-19 17:45:00; 1 stop(s) via MCI; 270 minutes. Local airport times.
  • WN3121: MSY 2026-12-19 13:15:00 → MCI 2026-12-19 15:15:00; layover at MCI: 65 minutes.
  • WN2694: MCI 2026-12-19 16:20:00 → MDW 2026-12-19 17:45:00.

2026-12-20 · one way · Axel-exclusive $214.50

• Southwest Airlines WN3347 / WN2321: MSY 2026-12-20 15:15:00 → MDW 2026-12-20 20:35:00; 1 stop(s) via RDU; 320 minutes. Local airport times.
  • WN3347: MSY 2026-12-20 15:15:00 → RDU 2026-12-20 18:20:00; layover at RDU: 75 minutes.
  • WN2321: RDU 2026-12-20 19:35:00 → MDW 2026-12-20 20:35:00.

2026-12-19 · one way · Axel-exclusive $214.50

• Southwest Airlines WN3347 / WN2321: MSY 2026-12-19 15:15:00 → MDW 2026-12-19 20:35:00; 1 stop(s) via RDU; 320 minutes. Local airport times.
  • WN3347: MSY 2026-12-19 15:15:00 → RDU 2026-12-19 18:20:00; layover at RDU: 75 minutes.
  • WN2321: RDU 2026-12-19 19:35:00 → MDW 2026-12-19 20:35:00.

2026-12-19 · one way · Axel-exclusive $214.50

• Southwest Airlines WN4792 / WN287: MSY 2026-12-19 07:25:00 → MDW 2026-12-19 12:05:00; 1 stop(s) via STL; 280 minutes. Local airport times.
  • WN4792: MSY 2026-12-19 07:25:00 → STL 2026-12-19 09:10:00; layover at STL: 105 minutes.
  • WN287: STL 2026-12-19 10:55:00 → MDW 2026-12-19 12:05:00.

2026-12-20 · one way · Axel-exclusive $214.50

• Southwest Airlines WN103 / WN1536: MSY 2026-12-20 16:00:00 → MDW 2026-12-20 20:25:00; 1 stop(s) via ATL; 265 minutes. Local airport times.
  • WN103: MSY 2026-12-20 16:00:00 → ATL 2026-12-20 18:25:00; layover at ATL: 70 minutes.
  • WN1536: ATL 2026-12-20 19:35:00 → MDW 2026-12-20 20:25:00.

2026-12-19 · one way · Axel-exclusive $214.50

• Southwest Airlines WN103 / WN1536: MSY 2026-12-19 16:00:00 → MDW 2026-12-19 20:25:00; 1 stop(s) via ATL; 265 minutes. Local airport times.
  • WN103: MSY 2026-12-19 16:00:00 → ATL 2026-12-19 18:25:00; layover at ATL: 70 minutes.
  • WN1536: ATL 2026-12-19 19:35:00 → MDW 2026-12-19 20:25:00.

2026-12-20 · one way · Axel-exclusive $214.50

• Southwest Airlines WN3121 / WN2694: MSY 2026-12-20 13:15:00 → MDW 2026-12-20 17:45:00; 1 stop(s) via MCI; 270 minutes. Local airport times.
  • WN3121: MSY 2026-12-20 13:15:00 → MCI 2026-12-20 15:15:00; layover at MCI: 65 minutes.
  • WN2694: MCI 2026-12-20 16:20:00 → MDW 2026-12-20 17:45:00.

2026-12-20 · one way · Axel-exclusive $214.50

• Southwest Airlines WN4879 / WN651: MSY 2026-12-20 17:00:00 → MDW 2026-12-20 21:05:00; 1 stop(s) via BNA; 245 minutes. Local airport times.
  • WN4879: MSY 2026-12-20 17:00:00 → BNA 2026-12-20 18:30:00; layover at BNA: 60 minutes.
  • WN651: BNA 2026-12-20 19:30:00 → MDW 2026-12-20 21:05:00.

2026-12-20 · one way · Axel-exclusive $286.00

• Delta Air Lines DL1322 / DL1728: MSY 2026-12-20 10:10:00 → MDW 2026-12-20 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2026-12-20 10:10:00 → ATL 2026-12-20 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2026-12-20 15:25:00 → MDW 2026-12-20 16:18:00.

2026-12-19 · one way · Axel-exclusive $286.00

• Delta Air Lines DL1322 / DL1728: MSY 2026-12-19 10:10:00 → MDW 2026-12-19 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2026-12-19 10:10:00 → ATL 2026-12-19 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2026-12-19 15:25:00 → MDW 2026-12-19 16:18:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

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