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New Orleans → Chicago

Jan 21, 2027 · return Jan 22, 2027

MSY → MDW1 adulteconomyRound trip

6 flight options · 1 airline

One-stop flights

Thu, Jan 21 – Fri, Jan 22

Southwest Airlines
10:10 amMSY
2h 20m
Nonstop
12:30 pmMDW
Southwest Airlines
1:20 pmMDW
4h 45m
ATL · 1h 20m
6:05 pmMSY

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Fri, Jan 22

Southwest Airlines
1:15 pmMSY
4h 30m
MCI · 1h 5m
5:45 pmMDW
Southwest Airlines
1:20 pmMDW
4h 45m
ATL · 1h 20m
6:05 pmMSY

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Fri, Jan 22

Southwest Airlines
3:15 pmMSY
5h 20m
RDU · 1h 15m
8:35 pmMDW
Southwest Airlines
1:20 pmMDW
4h 45m
ATL · 1h 20m
6:05 pmMSY

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Fri, Jan 22

Southwest Airlines
5:00 pmMSY
4h 5m
BNA · 1h
9:05 pmMDW
Southwest Airlines
1:20 pmMDW
4h 45m
ATL · 1h 20m
6:05 pmMSY

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Fri, Jan 22

Southwest Airlines
7:25 amMSY
4h 40m
STL · 1h 45m
12:05 pmMDW
Southwest Airlines
1:20 pmMDW
4h 45m
ATL · 1h 20m
6:05 pmMSY

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Fri, Jan 22

Southwest Airlines
4:00 pmMSY
4h 25m
ATL · 1h 10m
8:25 pmMDW
Southwest Airlines
1:20 pmMDW
4h 45m
ATL · 1h 20m
6:05 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 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
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)
2027-01-21 → 2027-01-22Southwest AirlinesWN3175 / WN2886 + WN240$300.002026-10-29T01:31:35Z
2027-01-21 → 2027-01-22Southwest AirlinesWN3121 + WN2694 / WN2886 + WN240$310.002026-10-29T01:31:35Z
2027-01-21 → 2027-01-22Southwest AirlinesWN3347 + WN2321 / WN2886 + WN240$310.002026-10-29T01:31:35Z
2027-01-21 → 2027-01-22Southwest AirlinesWN4879 + WN651 / WN2886 + WN240$310.002026-10-29T01:31:35Z
2027-01-21 → 2027-01-22Southwest AirlinesWN4792 + WN287 / WN2886 + WN240$310.002026-10-29T01:31:35Z
2027-01-21 → 2027-01-22Southwest AirlinesWN103 + WN1536 / WN2886 + WN240$310.002026-10-29T01:31:35Z

2027-01-21 → 2027-01-22 · $300.00

  • Southwest Airlines WN3175: MSY 2027-01-21 10:10:00 → MDW 2027-01-21 12:30:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN2886 / WN240: MDW 2027-01-22 13:20:00 → MSY 2027-01-22 18:05:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
    • WN2886: MDW 2027-01-22 13:20:00 → ATL 2027-01-22 16:10:00; layover at ATL: 80 minutes.
    • WN240: ATL 2027-01-22 17:30:00 → MSY 2027-01-22 18:05:00.

2027-01-21 → 2027-01-22 · $310.00

  • Southwest Airlines WN3121 / WN2694: MSY 2027-01-21 13:15:00 → MDW 2027-01-21 17:45:00; 1 stop(s) via MCI; 270 minutes. Local airport times.
    • WN3121: MSY 2027-01-21 13:15:00 → MCI 2027-01-21 15:15:00; layover at MCI: 65 minutes.
    • WN2694: MCI 2027-01-21 16:20:00 → MDW 2027-01-21 17:45:00.
  • Southwest Airlines WN2886 / WN240: MDW 2027-01-22 13:20:00 → MSY 2027-01-22 18:05:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
    • WN2886: MDW 2027-01-22 13:20:00 → ATL 2027-01-22 16:10:00; layover at ATL: 80 minutes.
    • WN240: ATL 2027-01-22 17:30:00 → MSY 2027-01-22 18:05:00.

2027-01-21 → 2027-01-22 · $310.00

  • Southwest Airlines WN3347 / WN2321: MSY 2027-01-21 15:15:00 → MDW 2027-01-21 20:35:00; 1 stop(s) via RDU; 320 minutes. Local airport times.
    • WN3347: MSY 2027-01-21 15:15:00 → RDU 2027-01-21 18:20:00; layover at RDU: 75 minutes.
    • WN2321: RDU 2027-01-21 19:35:00 → MDW 2027-01-21 20:35:00.
  • Southwest Airlines WN2886 / WN240: MDW 2027-01-22 13:20:00 → MSY 2027-01-22 18:05:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
    • WN2886: MDW 2027-01-22 13:20:00 → ATL 2027-01-22 16:10:00; layover at ATL: 80 minutes.
    • WN240: ATL 2027-01-22 17:30:00 → MSY 2027-01-22 18:05:00.

2027-01-21 → 2027-01-22 · $310.00

  • Southwest Airlines WN4879 / WN651: MSY 2027-01-21 17:00:00 → MDW 2027-01-21 21:05:00; 1 stop(s) via BNA; 245 minutes. Local airport times.
    • WN4879: MSY 2027-01-21 17:00:00 → BNA 2027-01-21 18:30:00; layover at BNA: 60 minutes.
    • WN651: BNA 2027-01-21 19:30:00 → MDW 2027-01-21 21:05:00.
  • Southwest Airlines WN2886 / WN240: MDW 2027-01-22 13:20:00 → MSY 2027-01-22 18:05:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
    • WN2886: MDW 2027-01-22 13:20:00 → ATL 2027-01-22 16:10:00; layover at ATL: 80 minutes.
    • WN240: ATL 2027-01-22 17:30:00 → MSY 2027-01-22 18:05:00.

2027-01-21 → 2027-01-22 · $310.00

  • Southwest Airlines WN4792 / WN287: MSY 2027-01-21 07:25:00 → MDW 2027-01-21 12:05:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN4792: MSY 2027-01-21 07:25:00 → STL 2027-01-21 09:10:00; layover at STL: 105 minutes.
    • WN287: STL 2027-01-21 10:55:00 → MDW 2027-01-21 12:05:00.
  • Southwest Airlines WN2886 / WN240: MDW 2027-01-22 13:20:00 → MSY 2027-01-22 18:05:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
    • WN2886: MDW 2027-01-22 13:20:00 → ATL 2027-01-22 16:10:00; layover at ATL: 80 minutes.
    • WN240: ATL 2027-01-22 17:30:00 → MSY 2027-01-22 18:05:00.

2027-01-21 → 2027-01-22 · $310.00

  • Southwest Airlines WN103 / WN1536: MSY 2027-01-21 16:00:00 → MDW 2027-01-21 20:25:00; 1 stop(s) via ATL; 265 minutes. Local airport times.
    • WN103: MSY 2027-01-21 16:00:00 → ATL 2027-01-21 18:25:00; layover at ATL: 70 minutes.
    • WN1536: ATL 2027-01-21 19:35:00 → MDW 2027-01-21 20:25:00.
  • Southwest Airlines WN2886 / WN240: MDW 2027-01-22 13:20:00 → MSY 2027-01-22 18:05:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
    • WN2886: MDW 2027-01-22 13:20:00 → ATL 2027-01-22 16:10:00; layover at ATL: 80 minutes.
    • WN240: ATL 2027-01-22 17:30:00 → MSY 2027-01-22 18:05:00.

More dates for this route