New Orleans (MSY) to Chicago (MDW) · Jan 9, 2027 · return Jan 17, 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

2027-01-09 → 2027-01-17 · Axel-exclusive $300.00

• Southwest Airlines WN1899: MSY 2027-01-09 14:35:00 → MDW 2027-01-09 16:55:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN2092 / WN1580: MDW 2027-01-17 14:30:00 → MSY 2027-01-17 19:40:00; 1 stop(s) via DAL; 310 minutes. Local airport times.
  • WN2092: MDW 2027-01-17 14:30:00 → DAL 2027-01-17 16:55:00; layover at DAL: 85 minutes.
  • WN1580: DAL 2027-01-17 18:20:00 → MSY 2027-01-17 19:40:00.

2027-01-09 → 2027-01-17 · Axel-exclusive $390.00

• Delta Air Lines DL1322 / DL1728: MSY 2027-01-09 10:10:00 → MDW 2027-01-09 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2027-01-09 10:10:00 → ATL 2027-01-09 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2027-01-09 15:25:00 → MDW 2027-01-09 16:18:00.
• Delta Air Lines DL4711 / DL1652: MDW 2027-01-17 09:30:00 → MSY 2027-01-17 16:16:00; 1 stop(s) via DTW; 406 minutes. Local airport times.
  • DL4711: MDW 2027-01-17 09:30:00 → DTW 2027-01-17 11:45:00; layover at DTW: 170 minutes.
  • DL1652: DTW 2027-01-17 14:35:00 → MSY 2027-01-17 16:16:00.

2027-01-09 → 2027-01-17 · Axel-exclusive $310.00

• Southwest Airlines WN103 / WN1536: MSY 2027-01-09 16:00:00 → MDW 2027-01-09 20:25:00; 1 stop(s) via ATL; 265 minutes. Local airport times.
  • WN103: MSY 2027-01-09 16:00:00 → ATL 2027-01-09 18:25:00; layover at ATL: 70 minutes.
  • WN1536: ATL 2027-01-09 19:35:00 → MDW 2027-01-09 20:25:00.
• Southwest Airlines WN2092 / WN1580: MDW 2027-01-17 14:30:00 → MSY 2027-01-17 19:40:00; 1 stop(s) via DAL; 310 minutes. Local airport times.
  • WN2092: MDW 2027-01-17 14:30:00 → DAL 2027-01-17 16:55:00; layover at DAL: 85 minutes.
  • WN1580: DAL 2027-01-17 18:20:00 → MSY 2027-01-17 19:40:00.

2027-01-09 → 2027-01-17 · Axel-exclusive $310.00

• Southwest Airlines WN4879 / WN651: MSY 2027-01-09 17:00:00 → MDW 2027-01-09 21:05:00; 1 stop(s) via BNA; 245 minutes. Local airport times.
  • WN4879: MSY 2027-01-09 17:00:00 → BNA 2027-01-09 18:30:00; layover at BNA: 60 minutes.
  • WN651: BNA 2027-01-09 19:30:00 → MDW 2027-01-09 21:05:00.
• Southwest Airlines WN2092 / WN1580: MDW 2027-01-17 14:30:00 → MSY 2027-01-17 19:40:00; 1 stop(s) via DAL; 310 minutes. Local airport times.
  • WN2092: MDW 2027-01-17 14:30:00 → DAL 2027-01-17 16:55:00; layover at DAL: 85 minutes.
  • WN1580: DAL 2027-01-17 18:20:00 → MSY 2027-01-17 19:40:00.

2027-01-09 → 2027-01-17 · Axel-exclusive $310.00

• Southwest Airlines WN3121 / WN2694: MSY 2027-01-09 13:15:00 → MDW 2027-01-09 17:45:00; 1 stop(s) via MCI; 270 minutes. Local airport times.
  • WN3121: MSY 2027-01-09 13:15:00 → MCI 2027-01-09 15:15:00; layover at MCI: 65 minutes.
  • WN2694: MCI 2027-01-09 16:20:00 → MDW 2027-01-09 17:45:00.
• Southwest Airlines WN2092 / WN1580: MDW 2027-01-17 14:30:00 → MSY 2027-01-17 19:40:00; 1 stop(s) via DAL; 310 minutes. Local airport times.
  • WN2092: MDW 2027-01-17 14:30:00 → DAL 2027-01-17 16:55:00; layover at DAL: 85 minutes.
  • WN1580: DAL 2027-01-17 18:20:00 → MSY 2027-01-17 19:40:00.

2027-01-09 → 2027-01-17 · Axel-exclusive $310.00

• Southwest Airlines WN4792 / WN287: MSY 2027-01-09 07:25:00 → MDW 2027-01-09 12:05:00; 1 stop(s) via STL; 280 minutes. Local airport times.
  • WN4792: MSY 2027-01-09 07:25:00 → STL 2027-01-09 09:10:00; layover at STL: 105 minutes.
  • WN287: STL 2027-01-09 10:55:00 → MDW 2027-01-09 12:05:00.
• Southwest Airlines WN2092 / WN1580: MDW 2027-01-17 14:30:00 → MSY 2027-01-17 19:40:00; 1 stop(s) via DAL; 310 minutes. Local airport times.
  • WN2092: MDW 2027-01-17 14:30:00 → DAL 2027-01-17 16:55:00; layover at DAL: 85 minutes.
  • WN1580: DAL 2027-01-17 18:20:00 → MSY 2027-01-17 19:40:00.

Explore this route

• All dates for this route
• Jan 8, 2027 · Return options
• Jan 10, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: New Orleans (MSY) to Chicago (MDW) · Jan 9, 2027 · return Jan 17, 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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