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

New Orleans (MSY) to Chicago (MDW), Nov 10–14, 2026: from $300 round trip

New Orleans (MSY) to Chicago (MDW), Nov 10–14, 2026: from $300 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $300 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 10–14, 2026, 1 adult, economy, checked Oct 29, 2026.

MSY → MDW1 adulteconomyRound trip

6 flight options · 2 airlines

One-stop flights

Tue, Nov 10 – Sat, Nov 14

Southwest Airlines
9:45 amMSY
2h 20m
Nonstop
12:05 pmMDW
Southwest Airlines
1:55 pmMDW
5h 5m
AUS · 1h 5m
7:00 pmMSY

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Tue, Nov 10 – Sat, Nov 14

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

Availability is checked when you select these flights.

Tue, Nov 10 – Sat, Nov 14

Southwest Airlines
4:00 pmMSY
4h 25m
ATL · 1h 10m
8:25 pmMDW
Southwest Airlines
1:55 pmMDW
5h 5m
AUS · 1h 5m
7:00 pmMSY

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Tue, Nov 10 – Sat, Nov 14

Southwest Airlines
3:15 pmMSY
5h 20m
RDU · 1h 15m
8:35 pmMDW
Southwest Airlines
1:55 pmMDW
5h 5m
AUS · 1h 5m
7:00 pmMSY

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Tue, Nov 10 – Sat, Nov 14

Southwest Airlines
7:25 amMSY
4h 40m
STL · 1h 45m
12:05 pmMDW
Southwest Airlines
1:55 pmMDW
5h 5m
AUS · 1h 5m
7:00 pmMSY

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Tue, Nov 10 – Sat, Nov 14

Southwest Airlines
5:00 pmMSY
4h 5m
BNA · 1h
9:05 pmMDW
Southwest Airlines
1:55 pmMDW
5h 5m
AUS · 1h 5m
7:00 pmMSY

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

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 routeNov 9, 2026 · Return optionsNov 11, 2026 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

New Orleans (MSY) to Chicago (MDW), Nov 10–14, 2026: from $300 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $300 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 10–14, 2026, 1 adult, economy, checked Oct 29, 2026. 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.

Exact travel datesAirlineFlightsTimes, duration, stopsTotal pricePrice issued (UTC)
2026-11-10 → 2026-11-14Southwest AirlinesWN2139 / WN2891 + WN39309:45:00→12:05:00 2h 20m nonstop · 13:55:00→19:00:00 5h 05m 1 stop via AUSAxel-exclusive $300.002026-10-29T01:31:35Z
2026-11-10 → 2026-11-14Delta Air LinesDL1322 + DL1728 / DL4711 + DL165210:10:00→16:18:00 6h 08m 1 stop via ATL · 09:30:00→16:16:00 6h 46m 1 stop via DTWAxel-exclusive $390.002026-10-29T01:31:35Z
2026-11-10 → 2026-11-14Southwest AirlinesWN103 + WN1536 / WN2891 + WN39316:00:00→20:25:00 4h 25m 1 stop via ATL · 13:55:00→19:00:00 5h 05m 1 stop via AUSAxel-exclusive $310.002026-10-29T01:31:35Z
2026-11-10 → 2026-11-14Southwest AirlinesWN3347 + WN2321 / WN2891 + WN39315:15:00→20:35:00 5h 20m 1 stop via RDU · 13:55:00→19:00:00 5h 05m 1 stop via AUSAxel-exclusive $310.002026-10-29T01:31:35Z
2026-11-10 → 2026-11-14Southwest AirlinesWN4792 + WN287 / WN2891 + WN39307:25:00→12:05:00 4h 40m 1 stop via STL · 13:55:00→19:00:00 5h 05m 1 stop via AUSAxel-exclusive $310.002026-10-29T01:31:35Z
2026-11-10 → 2026-11-14Southwest AirlinesWN4879 + WN651 / WN2891 + WN39317:00:00→21:05:00 4h 05m 1 stop via BNA · 13:55:00→19:00:00 5h 05m 1 stop via AUSAxel-exclusive $310.002026-10-29T01:31:35Z

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

2026-11-10 → 2026-11-14 · Axel-exclusive $300.00

  • Southwest Airlines WN2139: MSY 2026-11-10 09:45:00 → MDW 2026-11-10 12:05:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN2891 / WN393: MDW 2026-11-14 13:55:00 → MSY 2026-11-14 19:00:00; 1 stop(s) via AUS; 305 minutes. Local airport times.
    • WN2891: MDW 2026-11-14 13:55:00 → AUS 2026-11-14 16:35:00; layover at AUS: 65 minutes.
    • WN393: AUS 2026-11-14 17:40:00 → MSY 2026-11-14 19:00:00.

2026-11-10 → 2026-11-14 · Axel-exclusive $390.00

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

2026-11-10 → 2026-11-14 · Axel-exclusive $310.00

  • Southwest Airlines WN103 / WN1536: MSY 2026-11-10 16:00:00 → MDW 2026-11-10 20:25:00; 1 stop(s) via ATL; 265 minutes. Local airport times.
    • WN103: MSY 2026-11-10 16:00:00 → ATL 2026-11-10 18:25:00; layover at ATL: 70 minutes.
    • WN1536: ATL 2026-11-10 19:35:00 → MDW 2026-11-10 20:25:00.
  • Southwest Airlines WN2891 / WN393: MDW 2026-11-14 13:55:00 → MSY 2026-11-14 19:00:00; 1 stop(s) via AUS; 305 minutes. Local airport times.
    • WN2891: MDW 2026-11-14 13:55:00 → AUS 2026-11-14 16:35:00; layover at AUS: 65 minutes.
    • WN393: AUS 2026-11-14 17:40:00 → MSY 2026-11-14 19:00:00.

2026-11-10 → 2026-11-14 · Axel-exclusive $310.00

  • Southwest Airlines WN3347 / WN2321: MSY 2026-11-10 15:15:00 → MDW 2026-11-10 20:35:00; 1 stop(s) via RDU; 320 minutes. Local airport times.
    • WN3347: MSY 2026-11-10 15:15:00 → RDU 2026-11-10 18:20:00; layover at RDU: 75 minutes.
    • WN2321: RDU 2026-11-10 19:35:00 → MDW 2026-11-10 20:35:00.
  • Southwest Airlines WN2891 / WN393: MDW 2026-11-14 13:55:00 → MSY 2026-11-14 19:00:00; 1 stop(s) via AUS; 305 minutes. Local airport times.
    • WN2891: MDW 2026-11-14 13:55:00 → AUS 2026-11-14 16:35:00; layover at AUS: 65 minutes.
    • WN393: AUS 2026-11-14 17:40:00 → MSY 2026-11-14 19:00:00.

2026-11-10 → 2026-11-14 · Axel-exclusive $310.00

  • Southwest Airlines WN4792 / WN287: MSY 2026-11-10 07:25:00 → MDW 2026-11-10 12:05:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN4792: MSY 2026-11-10 07:25:00 → STL 2026-11-10 09:10:00; layover at STL: 105 minutes.
    • WN287: STL 2026-11-10 10:55:00 → MDW 2026-11-10 12:05:00.
  • Southwest Airlines WN2891 / WN393: MDW 2026-11-14 13:55:00 → MSY 2026-11-14 19:00:00; 1 stop(s) via AUS; 305 minutes. Local airport times.
    • WN2891: MDW 2026-11-14 13:55:00 → AUS 2026-11-14 16:35:00; layover at AUS: 65 minutes.
    • WN393: AUS 2026-11-14 17:40:00 → MSY 2026-11-14 19:00:00.

2026-11-10 → 2026-11-14 · Axel-exclusive $310.00

  • Southwest Airlines WN4879 / WN651: MSY 2026-11-10 17:00:00 → MDW 2026-11-10 21:05:00; 1 stop(s) via BNA; 245 minutes. Local airport times.
    • WN4879: MSY 2026-11-10 17:00:00 → BNA 2026-11-10 18:30:00; layover at BNA: 60 minutes.
    • WN651: BNA 2026-11-10 19:30:00 → MDW 2026-11-10 21:05:00.
  • Southwest Airlines WN2891 / WN393: MDW 2026-11-14 13:55:00 → MSY 2026-11-14 19:00:00; 1 stop(s) via AUS; 305 minutes. Local airport times.
    • WN2891: MDW 2026-11-14 13:55:00 → AUS 2026-11-14 16:35:00; layover at AUS: 65 minutes.
    • WN393: AUS 2026-11-14 17:40:00 → MSY 2026-11-14 19:00:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

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For AI assistants

  • This page: New Orleans (MSY) to Chicago (MDW) · Nov 10, 2026 · return Nov 14, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
  • 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. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. 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.