New Orleans (MSY) to Chicago (MDW) · Jan 1, 2027 · return Jan 11, 2027

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

2027-01-01 → 2027-01-11 · Axel-exclusive $326.25

• Southwest Airlines WN3174: MSY 2027-01-01 06:30:00 → MDW 2027-01-01 08:50:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN4747: MDW 2027-01-11 22:25:00 → MSY 2027-01-12 00:45:00; nonstop; 140 minutes. Local airport times.

2027-01-01 → 2027-01-11 · Axel-exclusive $438.75

• Delta Air Lines DL1322 / DL1728: MSY 2027-01-01 10:10:00 → MDW 2027-01-01 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2027-01-01 10:10:00 → ATL 2027-01-01 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2027-01-01 15:25:00 → MDW 2027-01-01 16:18:00.
• Delta Air Lines DL4711 / DL1652: MDW 2027-01-11 09:30:00 → MSY 2027-01-11 16:16:00; 1 stop(s) via DTW; 406 minutes. Local airport times.
  • DL4711: MDW 2027-01-11 09:30:00 → DTW 2027-01-11 11:45:00; layover at DTW: 170 minutes.
  • DL1652: DTW 2027-01-11 14:35:00 → MSY 2027-01-11 16:16:00.

2027-01-01 → 2027-01-11 · Axel-exclusive $326.25

• Southwest Airlines WN1899: MSY 2027-01-01 14:35:00 → MDW 2027-01-01 16:55:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN4747: MDW 2027-01-11 22:25:00 → MSY 2027-01-12 00:45:00; nonstop; 140 minutes. Local airport times.

2027-01-01 → 2027-01-11 · Axel-exclusive $338.75

• Southwest Airlines WN4879 / WN651: MSY 2027-01-01 17:00:00 → MDW 2027-01-01 21:05:00; 1 stop(s) via BNA; 245 minutes. Local airport times.
  • WN4879: MSY 2027-01-01 17:00:00 → BNA 2027-01-01 18:30:00; layover at BNA: 60 minutes.
  • WN651: BNA 2027-01-01 19:30:00 → MDW 2027-01-01 21:05:00.
• Southwest Airlines WN4747: MDW 2027-01-11 22:25:00 → MSY 2027-01-12 00:45:00; nonstop; 140 minutes. Local airport times.

2027-01-01 → 2027-01-11 · Axel-exclusive $338.75

• Southwest Airlines WN3347 / WN2321: MSY 2027-01-01 15:15:00 → MDW 2027-01-01 20:35:00; 1 stop(s) via RDU; 320 minutes. Local airport times.
  • WN3347: MSY 2027-01-01 15:15:00 → RDU 2027-01-01 18:20:00; layover at RDU: 75 minutes.
  • WN2321: RDU 2027-01-01 19:35:00 → MDW 2027-01-01 20:35:00.
• Southwest Airlines WN4747: MDW 2027-01-11 22:25:00 → MSY 2027-01-12 00:45:00; nonstop; 140 minutes. Local airport times.

2027-01-01 → 2027-01-11 · Axel-exclusive $338.75

• Southwest Airlines WN3121 / WN2694: MSY 2027-01-01 13:15:00 → MDW 2027-01-01 17:45:00; 1 stop(s) via MCI; 270 minutes. Local airport times.
  • WN3121: MSY 2027-01-01 13:15:00 → MCI 2027-01-01 15:15:00; layover at MCI: 65 minutes.
  • WN2694: MCI 2027-01-01 16:20:00 → MDW 2027-01-01 17:45:00.
• Southwest Airlines WN4747: MDW 2027-01-11 22:25:00 → MSY 2027-01-12 00:45:00; nonstop; 140 minutes. Local airport times.

2027-01-01 → 2027-01-11 · Axel-exclusive $338.75

• Southwest Airlines WN103 / WN1536: MSY 2027-01-01 16:00:00 → MDW 2027-01-01 20:25:00; 1 stop(s) via ATL; 265 minutes. Local airport times.
  • WN103: MSY 2027-01-01 16:00:00 → ATL 2027-01-01 18:25:00; layover at ATL: 70 minutes.
  • WN1536: ATL 2027-01-01 19:35:00 → MDW 2027-01-01 20:25:00.
• Southwest Airlines WN4747: MDW 2027-01-11 22:25:00 → MSY 2027-01-12 00:45:00; nonstop; 140 minutes. Local airport times.

2027-01-01 → 2027-01-11 · Axel-exclusive $338.75

• Southwest Airlines WN4792 / WN287: MSY 2027-01-01 07:25:00 → MDW 2027-01-01 12:05:00; 1 stop(s) via STL; 280 minutes. Local airport times.
  • WN4792: MSY 2027-01-01 07:25:00 → STL 2027-01-01 09:10:00; layover at STL: 105 minutes.
  • WN287: STL 2027-01-01 10:55:00 → MDW 2027-01-01 12:05:00.
• Southwest Airlines WN4747: MDW 2027-01-11 22:25:00 → MSY 2027-01-12 00:45:00; nonstop; 140 minutes. Local airport times.

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.

Explore this route

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For AI assistants

• This page: New Orleans (MSY) to Chicago (MDW) · Jan 1, 2027 · return Jan 11, 2027: 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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