Southwest Airlines New York to Chicago Flights

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Cheapflightsplus.com will find cheap Southwest Airlines flights from New York to Chicago. Compare airline ticket prices and book air tickets starting from $120 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 New York (NY) — Chicago (IL) 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 may: one-way - $120, two-way – $206.

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Cheap Flights from New York to Chicago by Southwest Airlines

Look at the list of plane tickets for the most popular direct and connecting flights by Southwest Airlines, their prices start from $120. The fastest nonstop flight takes 2h 25m. The fastest connecting flight — 5h 10m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $120 Find flight	9:15 am New York La Guardia	10:50 am Chicago Midway	2h 35m	Southwest Airlines	WN1634
from $120 Find flight	11:10 am New York La Guardia	12:40 pm Chicago Midway	2h 30m	Southwest Airlines	WN2234
from $120 Find flight	2:30 pm New York La Guardia	4:00 pm Chicago Midway	2h 30m	Southwest Airlines	WN2970
from $148 Find flight	9:55 pm New York La Guardia	11:20 pm Chicago Midway	2h 25m	Southwest Airlines	WN1192
from $148 Find flight	6:30 am New York La Guardia	8:00 am Chicago Midway	2h 30m	Southwest Airlines	WN761
from $149 Find flight	4:45 pm New York La Guardia	6:15 pm Chicago Midway	2h 30m	Southwest Airlines	WN2468
from $149 Find flight	6:55 pm New York La Guardia	8:25 pm Chicago Midway	2h 30m	Southwest Airlines	WN4246
from $160 Find flight	6:00 am New York La Guardia	1:00 pm Chicago O'Hare International	8h 0m layover 3h 40m - Nashville	Southwest Airlines	WN4189 WN983
from $161 Find flight	11:55 am New York La Guardia	5:20 pm Chicago Midway	6h 25m layover 1h 40m - North Kansas City	Southwest Airlines	WN2314 WN4928
from $169 Find flight	2:10 pm New York La Guardia	10:00 pm Chicago O'Hare International	8h 50m layover 4h 20m - Nashville	Southwest Airlines	WN679 WN4180
from $169 Find flight	11:20 am New York La Guardia	9:25 pm Chicago Midway	11h 5m layover 6h 30m - Atlanta	Southwest Airlines	WN2174 WN4703
from $169 Find flight	2:10 pm New York La Guardia	10:20 pm Chicago Midway	9h 10m layover 4h 55m - Nashville	Southwest Airlines	WN679 WN1647
from $169 Find flight	11:55 am New York La Guardia	8:15 pm Chicago Midway	9h 20m layover 4h 35m - North Kansas City	Southwest Airlines	WN2314 WN176
from $169 Find flight	9:50 am New York La Guardia	5:35 pm Chicago Midway	8h 45m layover 4h 30m - Nashville	Southwest Airlines	WN1800 WN477
from $188 Find flight	10:25 am New York La Guardia	8:05 pm Chicago Midway	10h 40m layover 6h 40m - Lake Saint Louis	Southwest Airlines	WN1962 WN1253
from $229 Find flight	7:20 am New York La Guardia	11:50 am Chicago Midway	5h 30m layover 1h 25m - Lake Saint Louis	Southwest Airlines	WN245 WN2364

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 04/24/2025

Southwest Airlines Flight Schedule New York to Chicago

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	Flight Details	Flight Time	Price
11:10 am — 12:40 pm	11:10 am — 12:40 pm WN2234 Southwest Airlines New York — Chicago	2h 30m	Find flight from$120
2:30 pm — 4:00 pm	2:30 pm — 4:00 pm WN2970 Southwest Airlines New York — Chicago	2h 30m	Find flight from$120
4:45 pm — 6:15 pm	4:45 pm — 6:15 pm WN2468 Southwest Airlines New York — Chicago	2h 30m	Find flight from$149
6:30 am — 8:00 am	6:30 am — 8:00 am WN761 Southwest Airlines New York — Chicago	2h 30m	Find flight from$148
6:55 pm — 8:25 pm	6:55 pm — 8:25 pm WN4246 Southwest Airlines New York — Chicago	2h 30m	Find flight from$149
9:15 am — 10:50 am	9:15 am — 10:50 am WN1634 Southwest Airlines New York — Chicago	2h 35m	Find flight from$120
9:55 pm — 11:20 pm	9:55 pm — 11:20 pm WN1192 Southwest Airlines New York — Chicago	2h 25m	Find flight from$148
10:25 am — 5:15 pm	10:25 am — 12:15 pm WN1962 Southwest Airlines New York — Lake Saint Louis 3h 50m stop 4:05 pm — 5:15 pm WN2973 Southwest Airlines Lake Saint Louis — Chicago	7h 50m including layover	Find flight from$161
10:25 am — 2:40 pm	10:25 am — 12:15 pm WN1962 Southwest Airlines New York — Lake Saint Louis 1h 20m stop 1:35 pm — 2:40 pm WN2906 Southwest Airlines Lake Saint Louis — Chicago	5h 15m including layover	Find flight from$161
11:55 am — 5:20 pm	11:55 am — 2:15 pm WN2314 Southwest Airlines New York — North Kansas City 1h 40m stop 3:55 pm — 5:20 pm WN4928 Southwest Airlines North Kansas City — Chicago	6h 25m including layover	Find flight from$161
2:10 pm — 10:00 pm	2:10 pm — 3:50 pm WN679 Southwest Airlines New York — Nashville 4h 20m stop 8:10 pm — 10:00 pm WN4180 Southwest Airlines Nashville — Chicago	8h 50m including layover	Find flight from$169
3:55 pm — 8:05 pm	3:55 pm — 5:50 pm WN3498 Southwest Airlines New York — Lake Saint Louis 1h 5m stop 6:55 pm — 8:05 pm WN1253 Southwest Airlines Lake Saint Louis — Chicago	5h 10m including layover	Find flight from$179
7:20 am — 5:15 pm	7:20 am — 9:15 am WN245 Southwest Airlines New York — Lake Saint Louis 6h 50m stop 4:05 pm — 5:15 pm WN2973 Southwest Airlines Lake Saint Louis — Chicago	10h 55m including layover	Find flight from$170
7:20 am — 2:40 pm	7:20 am — 9:15 am WN245 Southwest Airlines New York — Lake Saint Louis 4h 20m stop 1:35 pm — 2:40 pm WN2906 Southwest Airlines Lake Saint Louis — Chicago	8h 20m including layover	Find flight from$170

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times are local. Last updated on 04/24/2025

Flight Information

There are 7 flights by Southwest Airlines from New York to Chicago every week with departures from 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. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 10:25 am to 9:55 pm. Nonstop flight is 2h 25m. The time difference between New York and Chicago is 1h.

The fastest flight 2h 25m
Average flight time 2h 30m
The earliest flight 10:25 am
The latest flight 9:55 pm
Distance 711 ml

The cheapest months for traveling to Chicago are november (from 120 $).

The cheapest flight by Southwest Airlines that our users were able to find is $120. This airfare is economy class on one-way WN1634 flight for November 12, 2024 leaving La Guardia in New York at 9:15 am, it includes all taxes and additional fees.

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Southwest Airlines Airplanes on the Route

List of the most popular Southwest Airlines airplanes flying from New York to Chicago:

Airbus A320

from $120

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Boeing 737-800

from $148

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Boeing 737 MAX 8

from $149

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Boeing 737

from $160

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Other Popular Airlines on the Route

Besides Southwest Airlines there are other 2 airline carriers between New York and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from New York to Chicago.

Nonstop flights

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

AA - American Airlines

from $76

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See more direct flights

Connecting Flights

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

DL - Delta Air Lines Inc.

from $1031

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See more connecting flights

How to book an air ticket yourself?

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