New York (LGA) to Chicago (MDW) · Dec 24, 2026 · return Jan 7, 2027

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.

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

2026-12-24 → 2027-01-07 · Axel-exclusive $286.88

• Southwest Airlines WN2363 / WN4175: LGA 2026-12-24 13:05:00 → MDW 2026-12-24 20:00:00; 1 stop(s) via STL; 475 minutes. Local airport times.
  • WN2363: LGA 2026-12-24 13:05:00 → STL 2026-12-24 14:55:00; layover at STL: 240 minutes.
  • WN4175: STL 2026-12-24 18:55:00 → MDW 2026-12-24 20:00:00.
• Southwest Airlines WN725 / WN608: MDW 2027-01-07 09:55:00 → LGA 2027-01-07 17:25:00; 1 stop(s) via BNA; 390 minutes. Local airport times.
  • WN725: MDW 2027-01-07 09:55:00 → BNA 2027-01-07 11:30:00; layover at BNA: 160 minutes.
  • WN608: BNA 2027-01-07 14:10:00 → LGA 2027-01-07 17:25:00.

2026-12-24 → 2027-01-07 · Axel-exclusive $340.00

• Delta Air Lines DL1078 / DL4688: LGA 2026-12-24 09:25:00 → MDW 2026-12-24 13:01:00; 1 stop(s) via DTW; 276 minutes. Local airport times.
  • DL1078: LGA 2026-12-24 09:25:00 → DTW 2026-12-24 11:27:00; layover at DTW: 77 minutes.
  • DL4688: DTW 2026-12-24 12:44:00 → MDW 2026-12-24 13:01:00.
• Southwest Airlines WN725 / WN608: MDW 2027-01-07 09:55:00 → LGA 2027-01-07 17:25:00; 1 stop(s) via BNA; 390 minutes. Local airport times.
  • WN725: MDW 2027-01-07 09:55:00 → BNA 2027-01-07 11:30:00; layover at BNA: 160 minutes.
  • WN608: BNA 2027-01-07 14:10:00 → LGA 2027-01-07 17:25:00.

2026-12-24 → 2027-01-07 · Axel-exclusive $286.88

• Southwest Airlines WN2555 / WN1005: LGA 2026-12-24 07:00:00 → MDW 2026-12-24 12:55:00; 1 stop(s) via BNA; 415 minutes. Local airport times.
  • WN2555: LGA 2026-12-24 07:00:00 → BNA 2026-12-24 08:30:00; layover at BNA: 175 minutes.
  • WN1005: BNA 2026-12-24 11:25:00 → MDW 2026-12-24 12:55:00.
• Southwest Airlines WN725 / WN608: MDW 2027-01-07 09:55:00 → LGA 2027-01-07 17:25:00; 1 stop(s) via BNA; 390 minutes. Local airport times.
  • WN725: MDW 2027-01-07 09:55:00 → BNA 2027-01-07 11:30:00; layover at BNA: 160 minutes.
  • WN608: BNA 2027-01-07 14:10:00 → LGA 2027-01-07 17:25:00.

2026-12-24 → 2027-01-07 · Axel-exclusive $299.38

• Southwest Airlines WN2573: LGA 2026-12-24 06:30:00 → MDW 2026-12-24 07:55:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN725 / WN608: MDW 2027-01-07 09:55:00 → LGA 2027-01-07 17:25:00; 1 stop(s) via BNA; 390 minutes. Local airport times.
  • WN725: MDW 2027-01-07 09:55:00 → BNA 2027-01-07 11:30:00; layover at BNA: 160 minutes.
  • WN608: BNA 2027-01-07 14:10:00 → LGA 2027-01-07 17:25:00.

Explore this route

• All dates for this route
• Dec 23, 2026 · Return options
• Dec 25, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: New York (LGA) to Chicago (MDW) · Dec 24, 2026 · return Jan 7, 2027: 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 York 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.

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