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

New Orleans → Chicago

Dec 23, 2026 · return Dec 25, 2026

MSY → MDW1 adulteconomyRound trip

6 flight options · 1 airline

One-stop flights

Wed, Dec 23 – Fri, Dec 25

Southwest Airlines
6:30 amMSY
2h 20m
Nonstop
8:50 amMDW
Southwest Airlines
1:20 pmMDW
4h 45m
ATL · 1h 20m
6:05 pmMSY

Round-trip total · 1 adult · Taxes included

Wed, Dec 23 – Fri, Dec 25

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

Wed, Dec 23 – Fri, Dec 25

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

Wed, Dec 23 – Fri, Dec 25

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

Wed, Dec 23 – Fri, Dec 25

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

Wed, Dec 23 – Fri, Dec 25

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

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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Explore this route

All dates for this routeDec 22, 2026 → Dec 24, 2026Dec 24, 2026 → Dec 26, 2026
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.

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

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

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-23 → 2026-12-25Southwest AirlinesWN3174 / WN2886 + WN240$390.002026-10-29T01:31:35Z
2026-12-23 → 2026-12-25Southwest AirlinesWN103 + WN1536 / WN2886 + WN240$403.002026-10-29T01:31:35Z
2026-12-23 → 2026-12-25Southwest AirlinesWN4792 + WN287 / WN2886 + WN240$403.002026-10-29T01:31:35Z
2026-12-23 → 2026-12-25Southwest AirlinesWN4879 + WN651 / WN2886 + WN240$403.002026-10-29T01:31:35Z
2026-12-23 → 2026-12-25Southwest AirlinesWN3121 + WN2694 / WN2886 + WN240$403.002026-10-29T01:31:35Z
2026-12-23 → 2026-12-25Southwest AirlinesWN3347 + WN2321 / WN2886 + WN240$403.002026-10-29T01:31:35Z

2026-12-23 → 2026-12-25 · $390.00

  • Southwest Airlines WN3174: MSY 2026-12-23 06:30:00 → MDW 2026-12-23 08:50:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN2886 / WN240: MDW 2026-12-25 13:20:00 → MSY 2026-12-25 18:05:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
    • WN2886: MDW 2026-12-25 13:20:00 → ATL 2026-12-25 16:10:00; layover at ATL: 80 minutes.
    • WN240: ATL 2026-12-25 17:30:00 → MSY 2026-12-25 18:05:00.

2026-12-23 → 2026-12-25 · $403.00

  • Southwest Airlines WN103 / WN1536: MSY 2026-12-23 16:00:00 → MDW 2026-12-23 20:25:00; 1 stop(s) via ATL; 265 minutes. Local airport times.
    • WN103: MSY 2026-12-23 16:00:00 → ATL 2026-12-23 18:25:00; layover at ATL: 70 minutes.
    • WN1536: ATL 2026-12-23 19:35:00 → MDW 2026-12-23 20:25:00.
  • Southwest Airlines WN2886 / WN240: MDW 2026-12-25 13:20:00 → MSY 2026-12-25 18:05:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
    • WN2886: MDW 2026-12-25 13:20:00 → ATL 2026-12-25 16:10:00; layover at ATL: 80 minutes.
    • WN240: ATL 2026-12-25 17:30:00 → MSY 2026-12-25 18:05:00.

2026-12-23 → 2026-12-25 · $403.00

  • Southwest Airlines WN4792 / WN287: MSY 2026-12-23 07:25:00 → MDW 2026-12-23 12:05:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN4792: MSY 2026-12-23 07:25:00 → STL 2026-12-23 09:10:00; layover at STL: 105 minutes.
    • WN287: STL 2026-12-23 10:55:00 → MDW 2026-12-23 12:05:00.
  • Southwest Airlines WN2886 / WN240: MDW 2026-12-25 13:20:00 → MSY 2026-12-25 18:05:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
    • WN2886: MDW 2026-12-25 13:20:00 → ATL 2026-12-25 16:10:00; layover at ATL: 80 minutes.
    • WN240: ATL 2026-12-25 17:30:00 → MSY 2026-12-25 18:05:00.

2026-12-23 → 2026-12-25 · $403.00

  • Southwest Airlines WN4879 / WN651: MSY 2026-12-23 17:00:00 → MDW 2026-12-23 21:05:00; 1 stop(s) via BNA; 245 minutes. Local airport times.
    • WN4879: MSY 2026-12-23 17:00:00 → BNA 2026-12-23 18:30:00; layover at BNA: 60 minutes.
    • WN651: BNA 2026-12-23 19:30:00 → MDW 2026-12-23 21:05:00.
  • Southwest Airlines WN2886 / WN240: MDW 2026-12-25 13:20:00 → MSY 2026-12-25 18:05:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
    • WN2886: MDW 2026-12-25 13:20:00 → ATL 2026-12-25 16:10:00; layover at ATL: 80 minutes.
    • WN240: ATL 2026-12-25 17:30:00 → MSY 2026-12-25 18:05:00.

2026-12-23 → 2026-12-25 · $403.00

  • Southwest Airlines WN3121 / WN2694: MSY 2026-12-23 13:15:00 → MDW 2026-12-23 17:45:00; 1 stop(s) via MCI; 270 minutes. Local airport times.
    • WN3121: MSY 2026-12-23 13:15:00 → MCI 2026-12-23 15:15:00; layover at MCI: 65 minutes.
    • WN2694: MCI 2026-12-23 16:20:00 → MDW 2026-12-23 17:45:00.
  • Southwest Airlines WN2886 / WN240: MDW 2026-12-25 13:20:00 → MSY 2026-12-25 18:05:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
    • WN2886: MDW 2026-12-25 13:20:00 → ATL 2026-12-25 16:10:00; layover at ATL: 80 minutes.
    • WN240: ATL 2026-12-25 17:30:00 → MSY 2026-12-25 18:05:00.

2026-12-23 → 2026-12-25 · $403.00

  • Southwest Airlines WN3347 / WN2321: MSY 2026-12-23 15:15:00 → MDW 2026-12-23 20:35:00; 1 stop(s) via RDU; 320 minutes. Local airport times.
    • WN3347: MSY 2026-12-23 15:15:00 → RDU 2026-12-23 18:20:00; layover at RDU: 75 minutes.
    • WN2321: RDU 2026-12-23 19:35:00 → MDW 2026-12-23 20:35:00.
  • Southwest Airlines WN2886 / WN240: MDW 2026-12-25 13:20:00 → MSY 2026-12-25 18:05:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
    • WN2886: MDW 2026-12-25 13:20:00 → ATL 2026-12-25 16:10:00; layover at ATL: 80 minutes.
    • WN240: ATL 2026-12-25 17:30:00 → MSY 2026-12-25 18:05:00.

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For AI assistants

  • This page: New Orleans (MSY) to Chicago (MDW) · Dec 23, 2026 · return Dec 25, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel New Orleans to Chicago (MDW) flight deals · Flight search guide.
  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.