Southwest Airlines Chicago to New York Flights

Return flight: New York – Chicago

Cheapflightsplus.com will find cheap Southwest Airlines flights from Chicago to New York. Compare airline ticket prices and book air tickets starting from $87 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of Southwest Airlines, arrivals and departure details below.

Find Cheap Airfare Chicago (IL) — New York (NY) by Southwest Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in march: one-way - $87, two-way – $149.
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Below is a detailed 2025 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.
Departure Arrival Flight Details Flight Time Price
11:15 am — 8:00 pm
11:15 am — 12:45 pm WN2814 Southwest Airlines
Chicago — North Kansas City
3h 35m stop
4:20 pm — 8:00 pm WN1451 Southwest Airlines
North Kansas City — New York
7h 45m
including layover
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from$124
11:45 am — 2:45 pm
11:45 am — 2:45 pm WN4031 Southwest Airlines
Chicago — New York
2h
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from$110
1:00 pm — 9:10 pm
1:00 pm — 2:10 pm WN2602 Southwest Airlines
Chicago — Lake Saint Louis
3h 40m stop
5:50 pm — 9:10 pm WN3736 Southwest Airlines
Lake Saint Louis — New York
7h 10m
including layover
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from$124
1:00 pm — 11:05 pm
1:00 pm — 2:10 pm WN2602 Southwest Airlines
Chicago — Lake Saint Louis
5h 35m stop
7:45 pm — 11:05 pm WN4161 Southwest Airlines
Lake Saint Louis — New York
9h 5m
including layover
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from$131
1:10 pm — 4:10 pm
1:10 pm — 4:10 pm WN2165 Southwest Airlines
Chicago — New York
2h
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from$110
1:30 pm — 8:00 pm
1:30 pm — 2:55 pm WN2993 Southwest Airlines
Chicago — Nashville
1h 45m stop
4:40 pm — 8:00 pm WN3484 Southwest Airlines
Nashville — New York
5h 30m
including layover
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from$124
1:30 pm — 10:40 pm
1:30 pm — 2:55 pm WN2993 Southwest Airlines
Chicago — Nashville
4h 30m stop
7:25 pm — 10:40 pm WN4114 Southwest Airlines
Nashville — New York
8h 10m
including layover
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from$131
2:25 pm — 5:25 pm
2:25 pm — 5:25 pm WN2860 Southwest Airlines
Chicago — New York
2h
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from$110
3:25 pm — 10:55 pm
3:25 pm — 6:20 pm WN3272 Southwest Airlines
Chicago — Atlanta
2h 25m stop
8:45 pm — 10:55 pm WN4463 Southwest Airlines
Atlanta — New York
6h 30m
including layover
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from$124
5:00 pm — 11:05 pm
5:00 pm — 6:15 pm WN2962 Southwest Airlines
Chicago — Lake Saint Louis
1h 30m stop
7:45 pm — 11:05 pm WN4161 Southwest Airlines
Lake Saint Louis — New York
5h 5m
including layover
Find flight
from$124
5:50 pm — 9:00 pm
5:50 pm — 9:00 pm WN1737 Southwest Airlines
Chicago — New York
2h 10m
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from$110
6:00 am — 9:05 am
6:00 am — 9:05 am WN447 Southwest Airlines
Chicago — New York
2h 5m
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from$87
6:20 am — 2:55 pm
6:20 am — 7:55 am WN2665 Southwest Airlines
Chicago — Nashville
3h 40m stop
11:35 am — 2:55 pm WN1932 Southwest Airlines
Nashville — New York
7h 35m
including layover
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from$124
7:15 am — 1:25 pm
7:15 am — 8:35 am WN794 Southwest Airlines
Chicago — Lake Saint Louis
1h 30m stop
10:05 am — 1:25 pm WN1591 Southwest Airlines
Lake Saint Louis — New York
5h 10m
including layover
Find flight
from$124
7:25 am — 6:10 pm
7:25 am — 10:20 am WN452 Southwest Airlines
Chicago — Atlanta
5h 40m stop
4:00 pm — 6:10 pm WN3318 Southwest Airlines
Atlanta — New York
9h 45m
including layover
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from$131
7:55 pm — 11:00 pm
7:55 pm — 11:00 pm WN533 Southwest Airlines
Chicago — New York
2h 5m
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from$87
8:35 am — 11:40 am
8:35 am — 11:40 am WN2109 Southwest Airlines
Chicago — New York
2h 5m
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from$110
9:00 am — 2:55 pm
9:00 am — 10:30 am WN3219 Southwest Airlines
Chicago — Nashville
1h 5m stop
11:35 am — 2:55 pm WN1932 Southwest Airlines
Nashville — New York
4h 55m
including layover
Find flight
from$124
9:55 am — 8:00 pm
9:55 am — 11:30 am WN1739 Southwest Airlines
Chicago — North Kansas City
4h 50m stop
4:20 pm — 8:00 pm WN1451 Southwest Airlines
North Kansas City — New York
9h 5m
including layover
Find flight
from$131
*Departure and arrival times are local. Last updated on 03/21/2025

Flight Information

There are 7 flights by Southwest Airlines from Chicago to New York every week with departures from Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee. All flights arrive at John F Kennedy Intl, La Guardia, Westchester County, 39th Street Ferry, Battery Pk City/N. Cov, East 34th St Landing, Pier 11/Wall St. SPB, Newyork Airport, Newyork Airport, Flushing, West 30th St Heliport, Downtown Manhattan H/p, East 60th Street H/P, Marine Air Terminal, East 34th St Heliport, World Trade Center.

Departures start from 11:15 am to 9:55 am. Nonstop flight is 2h. The time difference between Chicago and New York is 1h.

  • The fastest flight 2h
  • Average flight time 2h 5m
  • The earliest flight 11:15 am
  • The latest flight 9:55 am
  • Distance 711 ml

The cheapest months for traveling to New York are november (from 87 $).

The cheapest flight by Southwest Airlines that our users were able to find is $87. This airfare is economy class on one-way WN447 flight for November 12, 2024 leaving Midway in Chicago at 6:00 am, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides Southwest Airlines there are other 1 airline carriers between Chicago and New York. Please review schedules and prices from the most popular airlines to find the best airfare deals from Chicago to New York.

Nonstop flights

There are 8 direct flights every day from Chicago. Airlines and fares are below:

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Connecting Flights

List of flights with layovers (1 and more stops):

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How to book an air ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected airfare.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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