Chicago (MDW) to New York (LGA), Dec 25–27, 2026, return Jan 1–3, 2027: from $349 round trip

Chicago (MDW) to New York (LGA), Dec 25–27, 2026, return Jan 1–3, 2027: from $349 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $349 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Dec 25, 2026 – Jan 1, 2027, 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 dates Airline Flights Times, duration, stops Total price Price issued (UTC)
2026-12-26 → 2027-01-03 Southwest Airlines WN4945 / WN2573 14:15:00→17:15:00 2h 00m nonstop · 06:30:00→07:55:00 2h 25m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-27 → 2027-01-03 Southwest Airlines WN2679 / WN2573 08:05:00→11:15:00 2h 10m nonstop · 06:30:00→07:55:00 2h 25m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-27 → 2027-01-01 Southwest Airlines WN2957 / WN2576 17:10:00→20:15:00 2h 05m nonstop · 12:30:00→14:05:00 2h 35m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-26 → 2027-01-01 Southwest Airlines WN2679 / WN2576 08:05:00→11:15:00 2h 10m nonstop · 12:30:00→14:05:00 2h 35m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-25 → 2027-01-02 Southwest Airlines WN4945 / WN206 14:15:00→17:15:00 2h 00m nonstop · 07:00:00→08:30:00 2h 30m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-26 → 2027-01-02 Southwest Airlines WN4945 / WN206 14:15:00→17:15:00 2h 00m nonstop · 07:00:00→08:30:00 2h 30m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-27 → 2027-01-02 Southwest Airlines WN2957 / WN206 17:10:00→20:15:00 2h 05m nonstop · 07:00:00→08:30:00 2h 30m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-25 → 2027-01-01 Southwest Airlines WN4945 / WN2576 14:15:00→17:15:00 2h 00m nonstop · 12:30:00→14:05:00 2h 35m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-25 → 2027-01-03 Southwest Airlines WN4945 / WN2573 14:15:00→17:15:00 2h 00m nonstop · 06:30:00→07:55:00 2h 25m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-26 → 2027-01-03 Southwest Airlines WN2679 / WN2573 08:05:00→11:15:00 2h 10m nonstop · 06:30:00→07:55:00 2h 25m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-27 → 2027-01-03 Southwest Airlines WN2957 / WN2573 17:10:00→20:15:00 2h 05m nonstop · 06:30:00→07:55:00 2h 25m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-26 → 2027-01-02 Southwest Airlines WN2679 / WN206 08:05:00→11:15:00 2h 10m nonstop · 07:00:00→08:30:00 2h 30m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-27 → 2027-01-02 Southwest Airlines WN2679 / WN206 08:05:00→11:15:00 2h 10m nonstop · 07:00:00→08:30:00 2h 30m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-25 → 2027-01-03 Southwest Airlines WN2958 / WN2573 19:15:00→22:20:00 2h 05m nonstop · 06:30:00→07:55:00 2h 25m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-25 → 2027-01-02 Southwest Airlines WN2958 / WN206 19:15:00→22:20:00 2h 05m nonstop · 07:00:00→08:30:00 2h 30m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-26 → 2027-01-01 Southwest Airlines WN4945 / WN2576 14:15:00→17:15:00 2h 00m nonstop · 12:30:00→14:05:00 2h 35m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-25 → 2027-01-01 Southwest Airlines WN2958 / WN2576 19:15:00→22:20:00 2h 05m nonstop · 12:30:00→14:05:00 2h 35m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-27 → 2027-01-01 Southwest Airlines WN2679 / WN2576 08:05:00→11:15:00 2h 10m nonstop · 12:30:00→14:05:00 2h 35m nonstop Axel-exclusive $355.25 2026-10-29T01:29:09Z
2026-12-25 → 2027-01-01 Southwest Airlines WN2737 + WN709 / WN2576 11:30:00→17:55:00 5h 25m 1 stop via STL · 12:30:00→14:05:00 2h 35m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-26 → 2027-01-02 Southwest Airlines WN725 + WN608 / WN206 09:55:00→17:25:00 6h 30m 1 stop via BNA · 07:00:00→08:30:00 2h 30m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-26 → 2027-01-01 Southwest Airlines WN2737 + WN709 / WN2576 11:30:00→17:55:00 5h 25m 1 stop via STL · 12:30:00→14:05:00 2h 35m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-26 → 2027-01-01 Southwest Airlines WN725 + WN608 / WN2576 09:55:00→17:25:00 6h 30m 1 stop via BNA · 12:30:00→14:05:00 2h 35m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-25 → 2027-01-03 Southwest Airlines WN725 + WN608 / WN2573 09:55:00→17:25:00 6h 30m 1 stop via BNA · 06:30:00→07:55:00 2h 25m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-25 → 2027-01-02 Southwest Airlines WN725 + WN608 / WN206 09:55:00→17:25:00 6h 30m 1 stop via BNA · 07:00:00→08:30:00 2h 30m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-26 → 2027-01-02 Southwest Airlines WN2737 + WN709 / WN206 11:30:00→17:55:00 5h 25m 1 stop via STL · 07:00:00→08:30:00 2h 30m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-26 → 2027-01-03 Southwest Airlines WN2737 + WN709 / WN2573 11:30:00→17:55:00 5h 25m 1 stop via STL · 06:30:00→07:55:00 2h 25m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-27 → 2027-01-03 Southwest Airlines WN2737 + WN709 / WN2573 11:30:00→17:55:00 5h 25m 1 stop via STL · 06:30:00→07:55:00 2h 25m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-27 → 2027-01-01 Southwest Airlines WN2737 + WN709 / WN2576 11:30:00→17:55:00 5h 25m 1 stop via STL · 12:30:00→14:05:00 2h 35m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-26 → 2027-01-03 Southwest Airlines WN725 + WN608 / WN2573 09:55:00→17:25:00 6h 30m 1 stop via BNA · 06:30:00→07:55:00 2h 25m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-25 → 2027-01-03 Southwest Airlines WN2737 + WN709 / WN2573 11:30:00→17:55:00 5h 25m 1 stop via STL · 06:30:00→07:55:00 2h 25m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-25 → 2027-01-02 Southwest Airlines WN2737 + WN709 / WN206 11:30:00→17:55:00 5h 25m 1 stop via STL · 07:00:00→08:30:00 2h 30m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-25 → 2027-01-01 Southwest Airlines WN725 + WN608 / WN2576 09:55:00→17:25:00 6h 30m 1 stop via BNA · 12:30:00→14:05:00 2h 35m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-27 → 2027-01-03 Southwest Airlines WN725 + WN608 / WN2573 09:55:00→17:25:00 6h 30m 1 stop via BNA · 06:30:00→07:55:00 2h 25m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-27 → 2027-01-02 Southwest Airlines WN2737 + WN709 / WN206 11:30:00→17:55:00 5h 25m 1 stop via STL · 07:00:00→08:30:00 2h 30m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-27 → 2027-01-01 Southwest Airlines WN725 + WN608 / WN2576 09:55:00→17:25:00 6h 30m 1 stop via BNA · 12:30:00→14:05:00 2h 35m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-27 → 2027-01-02 Southwest Airlines WN725 + WN608 / WN206 09:55:00→17:25:00 6h 30m 1 stop via BNA · 07:00:00→08:30:00 2h 30m nonstop Axel-exclusive $349.00 2026-10-29T01:29:09Z
2026-12-26 → 2027-01-03 Southwest Airlines WN4945 / WN2555 + WN1005 13:55:00→17:00:00 2h 05m nonstop · 07:00:00→12:55:00 6h 55m 1 stop via BNA Axel-exclusive $349.25 2026-10-29T01:29:09Z
2026-12-25 → 2027-01-03 Southwest Airlines WN4945 / WN2555 + WN1005 13:55:00→17:00:00 2h 05m nonstop · 07:00:00→12:55:00 6h 55m 1 stop via BNA Axel-exclusive $349.25 2026-10-29T01:29:09Z

Hotels in New York for these trips

Hotels: under a trip, hotels in New York 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.

All hotels in New York

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

2026-12-26 → 2027-01-03 · Axel-exclusive $355.25

2026-12-27 → 2027-01-03 · Axel-exclusive $355.25

2026-12-27 → 2027-01-01 · Axel-exclusive $355.25

2026-12-26 → 2027-01-01 · Axel-exclusive $355.25

2026-12-25 → 2027-01-02 · Axel-exclusive $355.25

2026-12-26 → 2027-01-02 · Axel-exclusive $355.25

2026-12-27 → 2027-01-02 · Axel-exclusive $355.25

2026-12-25 → 2027-01-01 · Axel-exclusive $355.25

2026-12-25 → 2027-01-03 · Axel-exclusive $355.25

2026-12-26 → 2027-01-03 · Axel-exclusive $355.25

2026-12-27 → 2027-01-03 · Axel-exclusive $355.25

2026-12-26 → 2027-01-02 · Axel-exclusive $355.25

2026-12-27 → 2027-01-02 · Axel-exclusive $355.25

2026-12-25 → 2027-01-03 · Axel-exclusive $355.25

2026-12-25 → 2027-01-02 · Axel-exclusive $355.25

2026-12-26 → 2027-01-01 · Axel-exclusive $355.25

2026-12-25 → 2027-01-01 · Axel-exclusive $355.25

2026-12-27 → 2027-01-01 · Axel-exclusive $355.25

2026-12-25 → 2027-01-01 · Axel-exclusive $349.00

2026-12-26 → 2027-01-02 · Axel-exclusive $349.00

2026-12-26 → 2027-01-01 · Axel-exclusive $349.00

2026-12-26 → 2027-01-01 · Axel-exclusive $349.00

2026-12-25 → 2027-01-03 · Axel-exclusive $349.00

2026-12-25 → 2027-01-02 · Axel-exclusive $349.00

2026-12-26 → 2027-01-02 · Axel-exclusive $349.00

2026-12-26 → 2027-01-03 · Axel-exclusive $349.00

2026-12-27 → 2027-01-03 · Axel-exclusive $349.00

2026-12-27 → 2027-01-01 · Axel-exclusive $349.00

2026-12-26 → 2027-01-03 · Axel-exclusive $349.00

2026-12-25 → 2027-01-03 · Axel-exclusive $349.00

2026-12-25 → 2027-01-02 · Axel-exclusive $349.00

2026-12-25 → 2027-01-01 · Axel-exclusive $349.00

2026-12-27 → 2027-01-03 · Axel-exclusive $349.00

2026-12-27 → 2027-01-02 · Axel-exclusive $349.00

2026-12-27 → 2027-01-01 · Axel-exclusive $349.00

2026-12-27 → 2027-01-02 · Axel-exclusive $349.00

2026-12-26 → 2027-01-03 · Axel-exclusive $349.25

2026-12-25 → 2027-01-03 · Axel-exclusive $349.25

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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