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Chicago → New York

Dec 21, 2026 · return Dec 28, 2026

MDW → LGA1 adulteconomyRound trip

4 flight options · 1 airline

Nonstop flights

Mon, Dec 21 – Mon, Dec 28

Southwest Airlines
1:55 pmMDW
2h 5m
Nonstop
5:00 pmLGA
Southwest Airlines
6:30 amLGA
2h 25m
Nonstop
7:55 amMDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Mon, Dec 28

Southwest Airlines
11:30 amMDW
5h 25m
STL · 1h 55m
5:55 pmLGA
Southwest Airlines
7:00 amLGA
6h 55m
BNA · 2h 55m
12:55 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

Southwest Airlines
9:55 amMDW
6h 30m
BNA · 2h 40m
5:25 pmLGA
Southwest Airlines
7:00 amLGA
6h 55m
BNA · 2h 55m
12:55 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

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

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ LGA

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 AirlinesWN4945 / WN2573$355.252026-10-29T01:29:09Z
2026-12-21 → 2026-12-28Southwest AirlinesWN2737 + WN709 / WN2555 + WN1005$343.002026-10-29T01:29:09Z
2026-12-21 → 2026-12-28Southwest AirlinesWN725 + WN608 / WN2555 + WN1005$343.002026-10-29T01:29:09Z
2026-12-21 → 2026-12-28Southwest AirlinesWN4945 / WN2555 + WN1005$349.252026-10-29T01:29:09Z

2026-12-21 → 2026-12-28 · $355.25

  • Southwest Airlines WN4945: MDW 2026-12-21 13:55:00 → LGA 2026-12-21 17:00:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN2573: LGA 2026-12-28 06:30:00 → MDW 2026-12-28 07:55:00; nonstop; 145 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $343.00

  • Southwest Airlines WN2737 / WN709: MDW 2026-12-21 11:30:00 → LGA 2026-12-21 17:55:00; 1 stop(s) via STL; 325 minutes. Local airport times.
    • WN2737: MDW 2026-12-21 11:30:00 → STL 2026-12-21 12:40:00; layover at STL: 115 minutes.
    • WN709: STL 2026-12-21 14:35:00 → LGA 2026-12-21 17:55:00.
  • Southwest Airlines WN2555 / WN1005: LGA 2026-12-28 07:00:00 → MDW 2026-12-28 12:55:00; 1 stop(s) via BNA; 415 minutes. Local airport times.
    • WN2555: LGA 2026-12-28 07:00:00 → BNA 2026-12-28 08:30:00; layover at BNA: 175 minutes.
    • WN1005: BNA 2026-12-28 11:25:00 → MDW 2026-12-28 12:55:00.

2026-12-21 → 2026-12-28 · $343.00

  • Southwest Airlines WN725 / WN608: MDW 2026-12-21 09:55:00 → LGA 2026-12-21 17:25:00; 1 stop(s) via BNA; 390 minutes. Local airport times.
    • WN725: MDW 2026-12-21 09:55:00 → BNA 2026-12-21 11:30:00; layover at BNA: 160 minutes.
    • WN608: BNA 2026-12-21 14:10:00 → LGA 2026-12-21 17:25:00.
  • Southwest Airlines WN2555 / WN1005: LGA 2026-12-28 07:00:00 → MDW 2026-12-28 12:55:00; 1 stop(s) via BNA; 415 minutes. Local airport times.
    • WN2555: LGA 2026-12-28 07:00:00 → BNA 2026-12-28 08:30:00; layover at BNA: 175 minutes.
    • WN1005: BNA 2026-12-28 11:25:00 → MDW 2026-12-28 12:55:00.

2026-12-21 → 2026-12-28 · $349.25

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

More dates for this route