New Orleans (MSY) to Chicago (MDW), Nov 16, 2026: round trips from $290, one way from $155

New Orleans (MSY) to Chicago (MDW), Nov 16, 2026: round trips from $290, one way from $155 on Axel, checked Oct 29, 2026. Lowest published fares: $290 round trip, Axel-exclusive, Southwest Airlines, nonstop, Nov 16–17, 2026; $155 one way, Axel-exclusive, Southwest Airlines, nonstop, Nov 16, 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.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and issuance times already shown here.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Nov 16–17, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Nov 16–18, 2026 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Nov 16–19, 2026 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Nov 16–20, 2026 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Nov 16–21, 2026 · 5 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Nov 16–22, 2026 · 6 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Nov 16–23, 2026 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Nov 16–24, 2026 · 8 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Nov 16–25, 2026 · 9 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Nov 16–26, 2026 · 10 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Nov 16–27, 2026 · 11 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Nov 16–28, 2026 · 12 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Nov 16–29, 2026 · 13 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Nov 16–30, 2026 · 14 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

All hotels in Chicago

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

2026-11-16 · one way · Axel-exclusive $155.00

• Southwest Airlines WN2139: MSY 2026-11-16 09:45:00 → MDW 2026-11-16 12:05:00; nonstop; 140 minutes. Local airport times.

2026-11-16 · one way · Axel-exclusive $220.00

• Delta Air Lines DL1322 / DL1728: MSY 2026-11-16 10:10:00 → MDW 2026-11-16 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2026-11-16 10:10:00 → ATL 2026-11-16 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2026-11-16 15:25:00 → MDW 2026-11-16 16:18:00.

2026-11-16 → 2026-11-17 · Axel-exclusive $290.00

• Southwest Airlines WN2139: MSY 2026-11-16 09:45:00 → MDW 2026-11-16 12:05:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN4747: MDW 2026-11-17 20:40:00 → MSY 2026-11-17 23:00:00; nonstop; 140 minutes. Local airport times.

2026-11-16 → 2026-11-17 · Axel-exclusive $390.00

• Delta Air Lines DL1322 / DL1728: MSY 2026-11-16 10:10:00 → MDW 2026-11-16 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2026-11-16 10:10:00 → ATL 2026-11-16 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2026-11-16 15:25:00 → MDW 2026-11-16 16:18:00.
• Delta Air Lines DL4711 / DL1652: MDW 2026-11-17 09:30:00 → MSY 2026-11-17 16:16:00; 1 stop(s) via DTW; 406 minutes. Local airport times.
  • DL4711: MDW 2026-11-17 09:30:00 → DTW 2026-11-17 11:45:00; layover at DTW: 170 minutes.
  • DL1652: DTW 2026-11-17 14:35:00 → MSY 2026-11-17 16:16:00.

2026-11-16 → 2026-11-18 · Axel-exclusive $290.00

• Southwest Airlines WN2139: MSY 2026-11-16 09:45:00 → MDW 2026-11-16 12:05:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN4747: MDW 2026-11-18 20:40:00 → MSY 2026-11-18 23:00:00; nonstop; 140 minutes. Local airport times.

2026-11-16 → 2026-11-18 · Axel-exclusive $390.00

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

2026-11-16 → 2026-11-19 · Axel-exclusive $290.00

• Southwest Airlines WN2139: MSY 2026-11-16 09:45:00 → MDW 2026-11-16 12:05:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN4747: MDW 2026-11-19 20:40:00 → MSY 2026-11-19 23:00:00; nonstop; 140 minutes. Local airport times.

2026-11-16 → 2026-11-19 · Axel-exclusive $390.00

• Delta Air Lines DL1322 / DL1728: MSY 2026-11-16 10:10:00 → MDW 2026-11-16 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2026-11-16 10:10:00 → ATL 2026-11-16 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2026-11-16 15:25:00 → MDW 2026-11-16 16:18:00.
• Delta Air Lines DL4711 / DL1652: MDW 2026-11-19 09:30:00 → MSY 2026-11-19 16:16:00; 1 stop(s) via DTW; 406 minutes. Local airport times.
  • DL4711: MDW 2026-11-19 09:30:00 → DTW 2026-11-19 11:45:00; layover at DTW: 170 minutes.
  • DL1652: DTW 2026-11-19 14:35:00 → MSY 2026-11-19 16:16:00.

2026-11-16 → 2026-11-20 · Axel-exclusive $300.00

• Southwest Airlines WN2139: MSY 2026-11-16 09:45:00 → MDW 2026-11-16 12:05:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN2886 / WN240: MDW 2026-11-20 13:20:00 → MSY 2026-11-20 18:05:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
  • WN2886: MDW 2026-11-20 13:20:00 → ATL 2026-11-20 16:10:00; layover at ATL: 80 minutes.
  • WN240: ATL 2026-11-20 17:30:00 → MSY 2026-11-20 18:05:00.

2026-11-16 → 2026-11-20 · Axel-exclusive $390.00

• Delta Air Lines DL1322 / DL1728: MSY 2026-11-16 10:10:00 → MDW 2026-11-16 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2026-11-16 10:10:00 → ATL 2026-11-16 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2026-11-16 15:25:00 → MDW 2026-11-16 16:18:00.
• Delta Air Lines DL4711 / DL1652: MDW 2026-11-20 09:30:00 → MSY 2026-11-20 16:16:00; 1 stop(s) via DTW; 406 minutes. Local airport times.
  • DL4711: MDW 2026-11-20 09:30:00 → DTW 2026-11-20 11:45:00; layover at DTW: 170 minutes.
  • DL1652: DTW 2026-11-20 14:35:00 → MSY 2026-11-20 16:16:00.

2026-11-16 → 2026-11-22 · Axel-exclusive $300.00

• Southwest Airlines WN2139: MSY 2026-11-16 09:45:00 → MDW 2026-11-16 12:05:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN2092 / WN1580: MDW 2026-11-22 14:30:00 → MSY 2026-11-22 19:40:00; 1 stop(s) via DAL; 310 minutes. Local airport times.
  • WN2092: MDW 2026-11-22 14:30:00 → DAL 2026-11-22 16:55:00; layover at DAL: 85 minutes.
  • WN1580: DAL 2026-11-22 18:20:00 → MSY 2026-11-22 19:40:00.

2026-11-16 → 2026-11-22 · Axel-exclusive $390.00

• Delta Air Lines DL1322 / DL1728: MSY 2026-11-16 10:10:00 → MDW 2026-11-16 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2026-11-16 10:10:00 → ATL 2026-11-16 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2026-11-16 15:25:00 → MDW 2026-11-16 16:18:00.
• Delta Air Lines DL4711 / DL1652: MDW 2026-11-22 09:30:00 → MSY 2026-11-22 16:16:00; 1 stop(s) via DTW; 406 minutes. Local airport times.
  • DL4711: MDW 2026-11-22 09:30:00 → DTW 2026-11-22 11:45:00; layover at DTW: 170 minutes.
  • DL1652: DTW 2026-11-22 14:35:00 → MSY 2026-11-22 16:16:00.

2026-11-16 → 2026-11-23 · Axel-exclusive $290.00

• Southwest Airlines WN2139: MSY 2026-11-16 09:45:00 → MDW 2026-11-16 12:05:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN4747: MDW 2026-11-23 20:40:00 → MSY 2026-11-23 23:00:00; nonstop; 140 minutes. Local airport times.

2026-11-16 → 2026-11-23 · Axel-exclusive $390.00

• Delta Air Lines DL1322 / DL1728: MSY 2026-11-16 10:10:00 → MDW 2026-11-16 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2026-11-16 10:10:00 → ATL 2026-11-16 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2026-11-16 15:25:00 → MDW 2026-11-16 16:18:00.
• Delta Air Lines DL4711 / DL1652: MDW 2026-11-23 09:30:00 → MSY 2026-11-23 16:16:00; 1 stop(s) via DTW; 406 minutes. Local airport times.
  • DL4711: MDW 2026-11-23 09:30:00 → DTW 2026-11-23 11:45:00; layover at DTW: 170 minutes.
  • DL1652: DTW 2026-11-23 14:35:00 → MSY 2026-11-23 16:16:00.

2026-11-16 → 2026-11-24 · Axel-exclusive $340.75

• Southwest Airlines WN2139: MSY 2026-11-16 09:45:00 → MDW 2026-11-16 12:05:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN4747: MDW 2026-11-24 20:40:00 → MSY 2026-11-24 23:00:00; nonstop; 140 minutes. Local airport times.

2026-11-16 → 2026-11-24 · Axel-exclusive $458.25

• Delta Air Lines DL1322 / DL1728: MSY 2026-11-16 10:10:00 → MDW 2026-11-16 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2026-11-16 10:10:00 → ATL 2026-11-16 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2026-11-16 15:25:00 → MDW 2026-11-16 16:18:00.
• Delta Air Lines DL4711 / DL1652: MDW 2026-11-24 09:30:00 → MSY 2026-11-24 16:16:00; 1 stop(s) via DTW; 406 minutes. Local airport times.
  • DL4711: MDW 2026-11-24 09:30:00 → DTW 2026-11-24 11:45:00; layover at DTW: 170 minutes.
  • DL1652: DTW 2026-11-24 14:35:00 → MSY 2026-11-24 16:16:00.

2026-11-16 → 2026-11-26 · Axel-exclusive $340.75

• Southwest Airlines WN2139: MSY 2026-11-16 09:45:00 → MDW 2026-11-16 12:05:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN4747: MDW 2026-11-26 20:40:00 → MSY 2026-11-26 23:00:00; nonstop; 140 minutes. Local airport times.

2026-11-16 → 2026-11-26 · Axel-exclusive $458.25

• Delta Air Lines DL1322 / DL1728: MSY 2026-11-16 10:10:00 → MDW 2026-11-16 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2026-11-16 10:10:00 → ATL 2026-11-16 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2026-11-16 15:25:00 → MDW 2026-11-16 16:18:00.
• Delta Air Lines DL4711 / DL1652: MDW 2026-11-26 09:30:00 → MSY 2026-11-26 16:16:00; 1 stop(s) via DTW; 406 minutes. Local airport times.
  • DL4711: MDW 2026-11-26 09:30:00 → DTW 2026-11-26 11:45:00; layover at DTW: 170 minutes.
  • DL1652: DTW 2026-11-26 14:35:00 → MSY 2026-11-26 16:16:00.

2026-11-16 → 2026-11-27 · Axel-exclusive $354.25

• Southwest Airlines WN2139: MSY 2026-11-16 09:45:00 → MDW 2026-11-16 12:05:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN2886 / WN240: MDW 2026-11-27 13:20:00 → MSY 2026-11-27 18:05:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
  • WN2886: MDW 2026-11-27 13:20:00 → ATL 2026-11-27 16:10:00; layover at ATL: 80 minutes.
  • WN240: ATL 2026-11-27 17:30:00 → MSY 2026-11-27 18:05:00.

2026-11-16 → 2026-11-27 · Axel-exclusive $458.25

• Delta Air Lines DL1322 / DL1728: MSY 2026-11-16 10:10:00 → MDW 2026-11-16 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2026-11-16 10:10:00 → ATL 2026-11-16 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2026-11-16 15:25:00 → MDW 2026-11-16 16:18:00.
• Delta Air Lines DL4711 / DL1652: MDW 2026-11-27 09:30:00 → MSY 2026-11-27 16:16:00; 1 stop(s) via DTW; 406 minutes. Local airport times.
  • DL4711: MDW 2026-11-27 09:30:00 → DTW 2026-11-27 11:45:00; layover at DTW: 170 minutes.
  • DL1652: DTW 2026-11-27 14:35:00 → MSY 2026-11-27 16:16:00.

2026-11-16 → 2026-11-28 · Axel-exclusive $354.25

• Southwest Airlines WN2139: MSY 2026-11-16 09:45:00 → MDW 2026-11-16 12:05:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN2891 / WN393: MDW 2026-11-28 13:55:00 → MSY 2026-11-28 19:00:00; 1 stop(s) via AUS; 305 minutes. Local airport times.
  • WN2891: MDW 2026-11-28 13:55:00 → AUS 2026-11-28 16:35:00; layover at AUS: 65 minutes.
  • WN393: AUS 2026-11-28 17:40:00 → MSY 2026-11-28 19:00:00.

2026-11-16 → 2026-11-28 · Axel-exclusive $458.25

• Delta Air Lines DL1322 / DL1728: MSY 2026-11-16 10:10:00 → MDW 2026-11-16 16:18:00; 1 stop(s) via ATL; 368 minutes. Local airport times.
  • DL1322: MSY 2026-11-16 10:10:00 → ATL 2026-11-16 12:36:00; layover at ATL: 169 minutes.
  • DL1728: ATL 2026-11-16 15:25:00 → MDW 2026-11-16 16:18:00.
• Delta Air Lines DL4711 / DL1652: MDW 2026-11-28 09:30:00 → MSY 2026-11-28 16:16:00; 1 stop(s) via DTW; 406 minutes. Local airport times.
  • DL4711: MDW 2026-11-28 09:30:00 → DTW 2026-11-28 11:45:00; layover at DTW: 170 minutes.
  • DL1652: DTW 2026-11-28 14:35:00 → MSY 2026-11-28 16:16:00.

2026-11-16 → 2026-11-30 · Axel-exclusive $340.75

• Southwest Airlines WN2139: MSY 2026-11-16 09:45:00 → MDW 2026-11-16 12:05:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN4747: MDW 2026-11-30 20:40:00 → MSY 2026-11-30 23:00:00; nonstop; 140 minutes. Local airport times.

2026-11-16 → 2026-11-30 · Axel-exclusive $458.25

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

Explore this route

• All dates for this route
• Nov 15, 2026 · Return options
• Nov 17, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: New Orleans (MSY) to Chicago (MDW) · Nov 16, 2026 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
• Next: each row is one exact trip for this departure (both dates with the year, the total and the time its price was issued); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested 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.

Feedback (optional): Missing info · Axel issue