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

New Orleans → Chicago

Dec 7, 2026 · return Dec 10, 2026

MSY → MDW1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Mon, Dec 7 – Thu, Dec 10

Southwest Airlines
9:45 amMSY
2h 20m
Nonstop
12:05 pmMDW
Southwest Airlines
10:25 pmMDW
2h 20m
Nonstop
12:45 am+1MSY

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Thu, Dec 10

Southwest Airlines
2:35 pmMSY
2h 20m
Nonstop
4:55 pmMDW
Southwest Airlines
10:25 pmMDW
2h 20m
Nonstop
12:45 am+1MSY

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 7 – Thu, Dec 10

Delta Air Lines
10:10 amMSY
6h 8m
ATL · 2h 49m
4:18 pmMDW
Delta Air Lines
9:30 amMDW
6h 46m
DTW · 2h 50m
4:16 pmMSY

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Thu, Dec 10

Southwest Airlines
3:15 pmMSY
5h 20m
RDU · 1h 15m
8:35 pmMDW
Southwest Airlines
10:25 pmMDW
2h 20m
Nonstop
12:45 am+1MSY

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Thu, Dec 10

Southwest Airlines
5:00 pmMSY
4h 5m
BNA · 1h
9:05 pmMDW
Southwest Airlines
10:25 pmMDW
2h 20m
Nonstop
12:45 am+1MSY

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Thu, Dec 10

Southwest Airlines
7:25 amMSY
4h 40m
STL · 1h 45m
12:05 pmMDW
Southwest Airlines
10:25 pmMDW
2h 20m
Nonstop
12:45 am+1MSY

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Thu, Dec 10

Southwest Airlines
4:00 pmMSY
4h 25m
ATL · 1h 10m
8:25 pmMDW
Southwest Airlines
10:25 pmMDW
2h 20m
Nonstop
12:45 am+1MSY

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Thu, Dec 10

Southwest Airlines
1:15 pmMSY
4h 30m
MCI · 1h 5m
5:45 pmMDW
Southwest Airlines
10:25 pmMDW
2h 20m
Nonstop
12:45 am+1MSY

Round-trip total · 1 adult · Taxes included

Make this trip yours

MSY ⇄ MDW

Economy

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All dates for this routeDec 6, 2026 → Dec 9, 2026Dec 8, 2026 → Dec 11, 2026
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Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

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

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-07 → 2026-12-10Southwest AirlinesWN2139 / WN4747$290.002026-10-29T01:31:35Z
2026-12-07 → 2026-12-10Delta Air LinesDL1322 + DL1728 / DL4711 + DL1652$390.002026-10-29T01:31:35Z
2026-12-07 → 2026-12-10Southwest AirlinesWN1899 / WN4747$290.002026-10-29T01:31:35Z
2026-12-07 → 2026-12-10Southwest AirlinesWN3347 + WN2321 / WN4747$300.002026-10-29T01:31:35Z
2026-12-07 → 2026-12-10Southwest AirlinesWN4879 + WN651 / WN4747$300.002026-10-29T01:31:35Z
2026-12-07 → 2026-12-10Southwest AirlinesWN4792 + WN287 / WN4747$300.002026-10-29T01:31:35Z
2026-12-07 → 2026-12-10Southwest AirlinesWN103 + WN1536 / WN4747$300.002026-10-29T01:31:35Z
2026-12-07 → 2026-12-10Southwest AirlinesWN3121 + WN2694 / WN4747$300.002026-10-29T01:31:35Z

2026-12-07 → 2026-12-10 · $290.00

  • Southwest Airlines WN2139: MSY 2026-12-07 09:45:00 → MDW 2026-12-07 12:05:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN4747: MDW 2026-12-10 22:25:00 → MSY 2026-12-11 00:45:00; nonstop; 140 minutes. Local airport times.

2026-12-07 → 2026-12-10 · $390.00

  • Delta Air Lines DL1322 / DL1728: MSY 2026-12-07 10:10:00 → MDW 2026-12-07 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
    • DL1322: MSY 2026-12-07 10:10:00 → ATL 2026-12-07 12:36:00; layover at ATL: 169 minutes.
    • DL1728: ATL 2026-12-07 15:25:00 → MDW 2026-12-07 16:18:00.
  • Delta Air Lines DL4711 / DL1652: MDW 2026-12-10 09:30:00 → MSY 2026-12-10 16:16:00; 1 stop(s) via DTW; 406 minutes. Local airport times.
    • DL4711: MDW 2026-12-10 09:30:00 → DTW 2026-12-10 11:45:00; layover at DTW: 170 minutes.
    • DL1652: DTW 2026-12-10 14:35:00 → MSY 2026-12-10 16:16:00.

2026-12-07 → 2026-12-10 · $290.00

  • Southwest Airlines WN1899: MSY 2026-12-07 14:35:00 → MDW 2026-12-07 16:55:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN4747: MDW 2026-12-10 22:25:00 → MSY 2026-12-11 00:45:00; nonstop; 140 minutes. Local airport times.

2026-12-07 → 2026-12-10 · $300.00

  • Southwest Airlines WN3347 / WN2321: MSY 2026-12-07 15:15:00 → MDW 2026-12-07 20:35:00; 1 stop(s) via RDU; 320 minutes. Local airport times.
    • WN3347: MSY 2026-12-07 15:15:00 → RDU 2026-12-07 18:20:00; layover at RDU: 75 minutes.
    • WN2321: RDU 2026-12-07 19:35:00 → MDW 2026-12-07 20:35:00.
  • Southwest Airlines WN4747: MDW 2026-12-10 22:25:00 → MSY 2026-12-11 00:45:00; nonstop; 140 minutes. Local airport times.

2026-12-07 → 2026-12-10 · $300.00

  • Southwest Airlines WN4879 / WN651: MSY 2026-12-07 17:00:00 → MDW 2026-12-07 21:05:00; 1 stop(s) via BNA; 245 minutes. Local airport times.
    • WN4879: MSY 2026-12-07 17:00:00 → BNA 2026-12-07 18:30:00; layover at BNA: 60 minutes.
    • WN651: BNA 2026-12-07 19:30:00 → MDW 2026-12-07 21:05:00.
  • Southwest Airlines WN4747: MDW 2026-12-10 22:25:00 → MSY 2026-12-11 00:45:00; nonstop; 140 minutes. Local airport times.

2026-12-07 → 2026-12-10 · $300.00

  • Southwest Airlines WN4792 / WN287: MSY 2026-12-07 07:25:00 → MDW 2026-12-07 12:05:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN4792: MSY 2026-12-07 07:25:00 → STL 2026-12-07 09:10:00; layover at STL: 105 minutes.
    • WN287: STL 2026-12-07 10:55:00 → MDW 2026-12-07 12:05:00.
  • Southwest Airlines WN4747: MDW 2026-12-10 22:25:00 → MSY 2026-12-11 00:45:00; nonstop; 140 minutes. Local airport times.

2026-12-07 → 2026-12-10 · $300.00

  • Southwest Airlines WN103 / WN1536: MSY 2026-12-07 16:00:00 → MDW 2026-12-07 20:25:00; 1 stop(s) via ATL; 265 minutes. Local airport times.
    • WN103: MSY 2026-12-07 16:00:00 → ATL 2026-12-07 18:25:00; layover at ATL: 70 minutes.
    • WN1536: ATL 2026-12-07 19:35:00 → MDW 2026-12-07 20:25:00.
  • Southwest Airlines WN4747: MDW 2026-12-10 22:25:00 → MSY 2026-12-11 00:45:00; nonstop; 140 minutes. Local airport times.

2026-12-07 → 2026-12-10 · $300.00

  • Southwest Airlines WN3121 / WN2694: MSY 2026-12-07 13:15:00 → MDW 2026-12-07 17:45:00; 1 stop(s) via MCI; 270 minutes. Local airport times.
    • WN3121: MSY 2026-12-07 13:15:00 → MCI 2026-12-07 15:15:00; layover at MCI: 65 minutes.
    • WN2694: MCI 2026-12-07 16:20:00 → MDW 2026-12-07 17:45:00.
  • Southwest Airlines WN4747: MDW 2026-12-10 22:25:00 → MSY 2026-12-11 00:45:00; nonstop; 140 minutes. Local airport times.

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