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New Orleans → Chicago

Dec 6, 2026 · return Dec 13, 2026

MSY → MDW1 adulteconomyRound trip

6 flight options · 1 airline

One-stop flights

Sun, Dec 6 – Sun, Dec 13

Southwest Airlines
6:30 amMSY
2h 20m
Nonstop
8:50 amMDW
Southwest Airlines
2:30 pmMDW
5h 10m
DAL · 1h 25m
7:40 pmMSY

Round-trip total · 1 adult · Taxes included

Sun, Dec 6 – Sun, Dec 13

Southwest Airlines
7:25 amMSY
4h 40m
STL · 1h 45m
12:05 pmMDW
Southwest Airlines
2:30 pmMDW
5h 10m
DAL · 1h 25m
7:40 pmMSY

Round-trip total · 1 adult · Taxes included

Sun, Dec 6 – Sun, Dec 13

Southwest Airlines
4:00 pmMSY
4h 25m
ATL · 1h 10m
8:25 pmMDW
Southwest Airlines
2:30 pmMDW
5h 10m
DAL · 1h 25m
7:40 pmMSY

Round-trip total · 1 adult · Taxes included

Sun, Dec 6 – Sun, Dec 13

Southwest Airlines
3:15 pmMSY
5h 20m
RDU · 1h 15m
8:35 pmMDW
Southwest Airlines
2:30 pmMDW
5h 10m
DAL · 1h 25m
7:40 pmMSY

Round-trip total · 1 adult · Taxes included

Sun, Dec 6 – Sun, Dec 13

Southwest Airlines
5:00 pmMSY
4h 5m
BNA · 1h
9:05 pmMDW
Southwest Airlines
2:30 pmMDW
5h 10m
DAL · 1h 25m
7:40 pmMSY

Round-trip total · 1 adult · Taxes included

Sun, Dec 6 – Sun, Dec 13

Southwest Airlines
1:15 pmMSY
4h 30m
MCI · 1h 5m
5:45 pmMDW
Southwest Airlines
2:30 pmMDW
5h 10m
DAL · 1h 25m
7:40 pmMSY

Round-trip total · 1 adult · Taxes included

Make this trip yours

MSY ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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More dates

All dates for this routeNov 5, 2026 → Nov 8, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Dec 5, 2026 → Dec 12, 2026Dec 17, 2026 → Dec 20, 2026Dec 26, 2026 → Jan 2, 2027Jan 5, 2027 · One wayJan 16, 2027 → Jan 23, 2027Feb 5, 2027 → Feb 8, 2027Apr 3, 2027 → Apr 10, 2027Jun 26, 2027 → Jul 3, 2027Sep 17, 2027 → Sep 20, 2027
For AI assistants: every fare, every link, instructions

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

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-06 → 2026-12-13Southwest AirlinesWN3174 / WN2092 + WN1580$300.002026-10-29T01:31:35Z
2026-12-06 → 2026-12-13Southwest AirlinesWN4792 + WN287 / WN2092 + WN1580$310.002026-10-29T01:31:35Z
2026-12-06 → 2026-12-13Southwest AirlinesWN103 + WN1536 / WN2092 + WN1580$310.002026-10-29T01:31:35Z
2026-12-06 → 2026-12-13Southwest AirlinesWN3347 + WN2321 / WN2092 + WN1580$310.002026-10-29T01:31:35Z
2026-12-06 → 2026-12-13Southwest AirlinesWN4879 + WN651 / WN2092 + WN1580$310.002026-10-29T01:31:35Z
2026-12-06 → 2026-12-13Southwest AirlinesWN3121 + WN2694 / WN2092 + WN1580$310.002026-10-29T01:31:35Z

2026-12-06 → 2026-12-13 · $300.00

  • Southwest Airlines WN3174: MSY 2026-12-06 06:30:00 → MDW 2026-12-06 08:50:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN2092 / WN1580: MDW 2026-12-13 14:30:00 → MSY 2026-12-13 19:40:00; 1 stop(s) via DAL; 310 minutes. Local airport times.
    • WN2092: MDW 2026-12-13 14:30:00 → DAL 2026-12-13 16:55:00; layover at DAL: 85 minutes.
    • WN1580: DAL 2026-12-13 18:20:00 → MSY 2026-12-13 19:40:00.

2026-12-06 → 2026-12-13 · $310.00

  • Southwest Airlines WN4792 / WN287: MSY 2026-12-06 07:25:00 → MDW 2026-12-06 12:05:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN4792: MSY 2026-12-06 07:25:00 → STL 2026-12-06 09:10:00; layover at STL: 105 minutes.
    • WN287: STL 2026-12-06 10:55:00 → MDW 2026-12-06 12:05:00.
  • Southwest Airlines WN2092 / WN1580: MDW 2026-12-13 14:30:00 → MSY 2026-12-13 19:40:00; 1 stop(s) via DAL; 310 minutes. Local airport times.
    • WN2092: MDW 2026-12-13 14:30:00 → DAL 2026-12-13 16:55:00; layover at DAL: 85 minutes.
    • WN1580: DAL 2026-12-13 18:20:00 → MSY 2026-12-13 19:40:00.

2026-12-06 → 2026-12-13 · $310.00

  • Southwest Airlines WN103 / WN1536: MSY 2026-12-06 16:00:00 → MDW 2026-12-06 20:25:00; 1 stop(s) via ATL; 265 minutes. Local airport times.
    • WN103: MSY 2026-12-06 16:00:00 → ATL 2026-12-06 18:25:00; layover at ATL: 70 minutes.
    • WN1536: ATL 2026-12-06 19:35:00 → MDW 2026-12-06 20:25:00.
  • Southwest Airlines WN2092 / WN1580: MDW 2026-12-13 14:30:00 → MSY 2026-12-13 19:40:00; 1 stop(s) via DAL; 310 minutes. Local airport times.
    • WN2092: MDW 2026-12-13 14:30:00 → DAL 2026-12-13 16:55:00; layover at DAL: 85 minutes.
    • WN1580: DAL 2026-12-13 18:20:00 → MSY 2026-12-13 19:40:00.

2026-12-06 → 2026-12-13 · $310.00

  • Southwest Airlines WN3347 / WN2321: MSY 2026-12-06 15:15:00 → MDW 2026-12-06 20:35:00; 1 stop(s) via RDU; 320 minutes. Local airport times.
    • WN3347: MSY 2026-12-06 15:15:00 → RDU 2026-12-06 18:20:00; layover at RDU: 75 minutes.
    • WN2321: RDU 2026-12-06 19:35:00 → MDW 2026-12-06 20:35:00.
  • Southwest Airlines WN2092 / WN1580: MDW 2026-12-13 14:30:00 → MSY 2026-12-13 19:40:00; 1 stop(s) via DAL; 310 minutes. Local airport times.
    • WN2092: MDW 2026-12-13 14:30:00 → DAL 2026-12-13 16:55:00; layover at DAL: 85 minutes.
    • WN1580: DAL 2026-12-13 18:20:00 → MSY 2026-12-13 19:40:00.

2026-12-06 → 2026-12-13 · $310.00

  • Southwest Airlines WN4879 / WN651: MSY 2026-12-06 17:00:00 → MDW 2026-12-06 21:05:00; 1 stop(s) via BNA; 245 minutes. Local airport times.
    • WN4879: MSY 2026-12-06 17:00:00 → BNA 2026-12-06 18:30:00; layover at BNA: 60 minutes.
    • WN651: BNA 2026-12-06 19:30:00 → MDW 2026-12-06 21:05:00.
  • Southwest Airlines WN2092 / WN1580: MDW 2026-12-13 14:30:00 → MSY 2026-12-13 19:40:00; 1 stop(s) via DAL; 310 minutes. Local airport times.
    • WN2092: MDW 2026-12-13 14:30:00 → DAL 2026-12-13 16:55:00; layover at DAL: 85 minutes.
    • WN1580: DAL 2026-12-13 18:20:00 → MSY 2026-12-13 19:40:00.

2026-12-06 → 2026-12-13 · $310.00

  • Southwest Airlines WN3121 / WN2694: MSY 2026-12-06 13:15:00 → MDW 2026-12-06 17:45:00; 1 stop(s) via MCI; 270 minutes. Local airport times.
    • WN3121: MSY 2026-12-06 13:15:00 → MCI 2026-12-06 15:15:00; layover at MCI: 65 minutes.
    • WN2694: MCI 2026-12-06 16:20:00 → MDW 2026-12-06 17:45:00.
  • Southwest Airlines WN2092 / WN1580: MDW 2026-12-13 14:30:00 → MSY 2026-12-13 19:40:00; 1 stop(s) via DAL; 310 minutes. Local airport times.
    • WN2092: MDW 2026-12-13 14:30:00 → DAL 2026-12-13 16:55:00; layover at DAL: 85 minutes.
    • WN1580: DAL 2026-12-13 18:20:00 → MSY 2026-12-13 19:40:00.

More dates for this route