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

Chicago → New York

Jun 25, 2027 · return Jun 28, 2027

MDW → LGA1 adulteconomyRound trip

3 flight options · 1 airline

One-stop flights

Fri, Jun 25 – Mon, Jun 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

Fri, Jun 25 – Mon, Jun 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

Fri, Jun 25 – Mon, Jun 28

Southwest Airlines
7:15 pmMDW
2h 5m
Nonstop
10:20 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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Explore this route

All dates for this routeJun 24, 2027 → Jun 27, 2027Jun 26, 2027 → Jun 29, 2027
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Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

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

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-06-25 → 2027-06-28Southwest AirlinesWN725 + WN608 / WN2555 + WN1005$320.002026-10-29T01:29:09Z
2027-06-25 → 2027-06-28Southwest AirlinesWN2737 + WN709 / WN2555 + WN1005$320.002026-10-29T01:29:09Z
2027-06-25 → 2027-06-28Southwest AirlinesWN2958 / WN2555 + WN1005$330.002026-10-29T01:29:09Z

2027-06-25 → 2027-06-28 · $320.00

  • Southwest Airlines WN725 / WN608: MDW 2027-06-25 09:55:00 → LGA 2027-06-25 17:25:00; 1 stop(s) via BNA; 390 minutes. Local airport times.
    • WN725: MDW 2027-06-25 09:55:00 → BNA 2027-06-25 11:30:00; layover at BNA: 160 minutes.
    • WN608: BNA 2027-06-25 14:10:00 → LGA 2027-06-25 17:25:00.
  • Southwest Airlines WN2555 / WN1005: LGA 2027-06-28 07:00:00 → MDW 2027-06-28 12:55:00; 1 stop(s) via BNA; 415 minutes. Local airport times.
    • WN2555: LGA 2027-06-28 07:00:00 → BNA 2027-06-28 08:30:00; layover at BNA: 175 minutes.
    • WN1005: BNA 2027-06-28 11:25:00 → MDW 2027-06-28 12:55:00.

2027-06-25 → 2027-06-28 · $320.00

  • Southwest Airlines WN2737 / WN709: MDW 2027-06-25 11:30:00 → LGA 2027-06-25 17:55:00; 1 stop(s) via STL; 325 minutes. Local airport times.
    • WN2737: MDW 2027-06-25 11:30:00 → STL 2027-06-25 12:40:00; layover at STL: 115 minutes.
    • WN709: STL 2027-06-25 14:35:00 → LGA 2027-06-25 17:55:00.
  • Southwest Airlines WN2555 / WN1005: LGA 2027-06-28 07:00:00 → MDW 2027-06-28 12:55:00; 1 stop(s) via BNA; 415 minutes. Local airport times.
    • WN2555: LGA 2027-06-28 07:00:00 → BNA 2027-06-28 08:30:00; layover at BNA: 175 minutes.
    • WN1005: BNA 2027-06-28 11:25:00 → MDW 2027-06-28 12:55:00.

2027-06-25 → 2027-06-28 · $330.00

  • Southwest Airlines WN2958: MDW 2027-06-25 19:15:00 → LGA 2027-06-25 22:20:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN2555 / WN1005: LGA 2027-06-28 07:00:00 → MDW 2027-06-28 12:55:00; 1 stop(s) via BNA; 415 minutes. Local airport times.
    • WN2555: LGA 2027-06-28 07:00:00 → BNA 2027-06-28 08:30:00; layover at BNA: 175 minutes.
    • WN1005: BNA 2027-06-28 11:25:00 → MDW 2027-06-28 12:55:00.

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