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New York → Chicago

Dec 21, 2026 · return Dec 28, 2026

LGA → MDW1 adulteconomyRound trip

5 flight options · 2 airlines

Nonstop flights

Mon, Dec 21 – Mon, Dec 28

Southwest Airlines
6:30 amLGA
2h 25m
Nonstop
7:55 amMDW
Southwest Airlines
2:15 pmMDW
2h
Nonstop
5:15 pmLGA

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

Southwest Airlines
3:00 pmLGA
2h 35m
Nonstop
4:35 pmMDW
Southwest Airlines
2:15 pmMDW
2h
Nonstop
5:15 pmLGA

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Mon, Dec 28

Delta Air Lines
9:25 amLGA
4h 36m
DTW · 1h 17m
1:01 pmMDW
Southwest Airlines
2:15 pmMDW
2h
Nonstop
5:15 pmLGA

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

Southwest Airlines
1:05 pmLGA
7h 55m
STL · 4h
8:00 pmMDW
Southwest Airlines
2:15 pmMDW
2h
Nonstop
5:15 pmLGA

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

Southwest Airlines
7:00 amLGA
6h 55m
BNA · 2h 55m
12:55 pmMDW
Southwest Airlines
2:15 pmMDW
2h
Nonstop
5:15 pmLGA

Round-trip total · 1 adult · Taxes included

Make this trip yours

LGA ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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More dates

All dates for this routeNov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
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.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-21 → 2026-12-28Southwest AirlinesWN2573 / WN4945$336.882026-10-29T01:26:39Z
2026-12-21 → 2026-12-28Delta Air Lines / Southwest AirlinesDL1078 + DL4688 / WN4945$377.502026-10-29T01:26:39Z
2026-12-21 → 2026-12-28Southwest AirlinesWN4234 / WN4945$336.882026-10-29T01:26:39Z
2026-12-21 → 2026-12-28Southwest AirlinesWN2363 + WN4175 / WN4945$324.382026-10-29T01:26:39Z
2026-12-21 → 2026-12-28Southwest AirlinesWN2555 + WN1005 / WN4945$324.382026-10-29T01:26:39Z

2026-12-21 → 2026-12-28 · $336.88

  • Southwest Airlines WN2573: LGA 2026-12-21 06:30:00 → MDW 2026-12-21 07:55:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN4945: MDW 2026-12-28 14:15:00 → LGA 2026-12-28 17:15:00; nonstop; 120 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $377.50

  • Delta Air Lines DL1078 / DL4688: LGA 2026-12-21 09:25:00 → MDW 2026-12-21 13:01:00; 1 stop(s) via DTW; 276 minutes. Local airport times.
    • DL1078: LGA 2026-12-21 09:25:00 → DTW 2026-12-21 11:27:00; layover at DTW: 77 minutes.
    • DL4688: DTW 2026-12-21 12:44:00 → MDW 2026-12-21 13:01:00.
  • Southwest Airlines WN4945: MDW 2026-12-28 14:15:00 → LGA 2026-12-28 17:15:00; nonstop; 120 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $336.88

  • Southwest Airlines WN4234: LGA 2026-12-21 15:00:00 → MDW 2026-12-21 16:35:00; nonstop; 155 minutes. Local airport times.
  • Southwest Airlines WN4945: MDW 2026-12-28 14:15:00 → LGA 2026-12-28 17:15:00; nonstop; 120 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $324.38

  • Southwest Airlines WN2363 / WN4175: LGA 2026-12-21 13:05:00 → MDW 2026-12-21 20:00:00; 1 stop(s) via STL; 475 minutes. Local airport times.
    • WN2363: LGA 2026-12-21 13:05:00 → STL 2026-12-21 14:55:00; layover at STL: 240 minutes.
    • WN4175: STL 2026-12-21 18:55:00 → MDW 2026-12-21 20:00:00.
  • Southwest Airlines WN4945: MDW 2026-12-28 14:15:00 → LGA 2026-12-28 17:15:00; nonstop; 120 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $324.38

  • Southwest Airlines WN2555 / WN1005: LGA 2026-12-21 07:00:00 → MDW 2026-12-21 12:55:00; 1 stop(s) via BNA; 415 minutes. Local airport times.
    • WN2555: LGA 2026-12-21 07:00:00 → BNA 2026-12-21 08:30:00; layover at BNA: 175 minutes.
    • WN1005: BNA 2026-12-21 11:25:00 → MDW 2026-12-21 12:55:00.
  • Southwest Airlines WN4945: MDW 2026-12-28 14:15:00 → LGA 2026-12-28 17:15:00; nonstop; 120 minutes. Local airport times.

More dates for this route