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 $244 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 august: one-way - $244, two-way – $418.

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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 $244. The fastest nonstop flight takes 2h 20m. The fastest connecting flight — 5h 55m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $309 Find flight	7:30 am New York La Guardia	8:50 am Chicago Midway	2h 20m	Southwest Airlines	WN4429
from $330 Find flight	1:50 pm New York La Guardia	3:10 pm Chicago Midway	2h 20m	Southwest Airlines	WN3458
from $341 Find flight	10:55 am New York La Guardia	12:20 pm Chicago Midway	2h 25m	Southwest Airlines	WN3457
from $465 Find flight	4:35 pm New York La Guardia	6:05 pm Chicago Midway	2h 30m	Southwest Airlines	WN3459
from $244 Find flight	6:20 am New York La Guardia	1:05 pm Chicago O'Hare International	7h 45m layover 1h 5m - Denver	Southwest Airlines	WN3447 WN1195
from $250 Find flight	8:15 am New York La Guardia	4:25 pm Chicago O'Hare International	9h 10m layover 4h 55m - Nashville	Southwest Airlines	WN2943 WN1204
from $266 Find flight	11:25 am New York La Guardia	4:25 pm Chicago O'Hare International	6h 0m layover 1h 40m - Nashville	Southwest Airlines	WN3443 WN1204
from $303 Find flight	1:30 pm New York La Guardia	6:25 pm Chicago Midway	5h 55m layover 1h 30m - North Kansas City	Southwest Airlines	WN1594 WN3321
from $363 Find flight	8:15 am New York La Guardia	1:10 pm Chicago Midway	5h 55m layover 1h 40m - Atlanta	Southwest Airlines	WN428 WN429
from $363 Find flight	8:15 am New York La Guardia	2:45 pm Chicago Midway	7h 30m layover 3h 30m - Nashville	Southwest Airlines	WN2943 WN1147
from $394 Find flight	9:30 am New York La Guardia	2:50 pm Chicago Midway	6h 20m layover 2h 35m - Lake Saint Louis	Southwest Airlines	WN1580 WN2328
from $400 Find flight	9:30 am New York La Guardia	7:05 pm Chicago Midway	10h 35m layover 6h 50m - Lake Saint Louis	Southwest Airlines	WN1580 WN4463
from $460 Find flight	8:15 am New York La Guardia	6:35 pm Chicago Midway	11h 20m layover 7h 20m - Nashville	Southwest Airlines	WN2943 WN3575
from $271 Find flight	2:15 pm New York La Guardia	10:00 pm Chicago O'Hare International	8h 45m layover 1h 0m - Atlanta 0h 40m - Dallas	Southwest Airlines	WN360 WN1057 WN2281
from $287 Find flight	9:00 am New York La Guardia	10:00 pm Chicago O'Hare International	14h 0m layover 2h 40m - Houston 3h 55m - Dallas	Southwest Airlines	WN2968 WN34 WN2281
from $287 Find flight	9:00 am New York La Guardia	10:00 pm Chicago O'Hare International	14h 0m layover 3h 50m - Houston 2h 45m - Dallas	Southwest Airlines	WN2968 WN38 WN2281

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 08/13/2025

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
10:55 am — 12:20 pm	10:55 am — 12:20 pm WN3457 Southwest Airlines New York — Chicago	2h 25m	Find flight from$341
11:25 am — 4:25 pm	11:25 am — 12:55 pm WN3443 Southwest Airlines New York — Nashville 1h 40m stop 2:35 pm — 4:25 pm WN1204 Southwest Airlines Nashville — Chicago	6h including layover	Find flight from$266
11:25 am — 6:35 pm	11:25 am — 12:55 pm WN3443 Southwest Airlines New York — Nashville 4h 5m stop 5:00 pm — 6:35 pm WN3575 Southwest Airlines Nashville — Chicago	8h 10m including layover	Find flight from$482
12:20 pm — 1:40 pm	12:20 pm — 1:40 pm WN1704 Southwest Airlines New York — Chicago	2h 20m	Find flight from$530
1:30 pm — 10:00 pm	1:30 pm — 3:30 pm WN1594 Southwest Airlines New York — North Kansas City 1h 55m stop 5:25 pm — 6:55 pm WN2370 Southwest Airlines North Kansas City — Dallas 40m stop 7:35 pm — 10:00 pm WN2281 Southwest Airlines Dallas — Chicago	9h 30m including layover	Find flight from$271
1:30 pm — 6:25 pm	1:30 pm — 3:30 pm WN1594 Southwest Airlines New York — North Kansas City 1h 30m stop 5:00 pm — 6:25 pm WN3321 Southwest Airlines North Kansas City — Chicago	5h 55m including layover	Find flight from$303
1:50 pm — 3:10 pm	1:50 pm — 3:10 pm WN3458 Southwest Airlines New York — Chicago	2h 20m	Find flight from$330
2:10 pm — 7:05 pm	2:10 pm — 3:55 pm WN1385 Southwest Airlines New York — Lake Saint Louis 2h 5m stop 6:00 pm — 7:05 pm WN4463 Southwest Airlines Lake Saint Louis — Chicago	5h 55m including layover	Find flight from$477
2:15 pm — 10:00 pm	2:15 pm — 4:45 pm WN360 Southwest Airlines New York — Atlanta 1h stop 5:45 pm — 6:55 pm WN1057 Southwest Airlines Atlanta — Dallas 40m stop 7:35 pm — 10:00 pm WN2281 Southwest Airlines Dallas — Chicago	8h 45m including layover	Find flight from$271
4:35 pm — 6:05 pm	4:35 pm — 6:05 pm WN3459 Southwest Airlines New York — Chicago	2h 30m	Find flight from$465
6:20 am — 1:05 pm	6:20 am — 8:30 am WN3447 Southwest Airlines New York — Denver 1h 5m stop 9:35 am — 1:05 pm WN1195 Southwest Airlines Denver — Chicago	7h 45m including layover	Find flight from$244
6:20 am — 4:45 pm	6:20 am — 8:30 am WN3447 Southwest Airlines New York — Denver 4h 45m stop 1:15 pm — 4:45 pm WN661 Southwest Airlines Denver — Chicago	11h 25m including layover	Find flight from$254
7:30 am — 8:50 am	7:30 am — 8:50 am WN4429 Southwest Airlines New York — Chicago	2h 20m	Find flight from$309
8:15 am — 4:25 pm	8:15 am — 9:40 am WN2943 Southwest Airlines New York — Nashville 4h 55m stop 2:35 pm — 4:25 pm WN1204 Southwest Airlines Nashville — Chicago	9h 10m including layover	Find flight from$250
8:15 am — 1:10 pm	8:15 am — 10:40 am WN428 Southwest Airlines New York — Atlanta 1h 40m stop 12:20 pm — 1:10 pm WN429 Southwest Airlines Atlanta — Chicago	5h 55m including layover	Find flight from$363
8:15 am — 2:45 pm	8:15 am — 9:40 am WN2943 Southwest Airlines New York — Nashville 3h 30m stop 1:10 pm — 2:45 pm WN1147 Southwest Airlines Nashville — Chicago	7h 30m including layover	Find flight from$363
8:15 am — 6:10 pm	8:15 am — 10:40 am WN428 Southwest Airlines New York — Atlanta 6h 35m stop 5:15 pm — 6:10 pm WN1689 Southwest Airlines Atlanta — Chicago	10h 55m including layover	Find flight from$369
8:15 am — 6:35 pm	8:15 am — 9:40 am WN2943 Southwest Airlines New York — Nashville 7h 20m stop 5:00 pm — 6:35 pm WN3575 Southwest Airlines Nashville — Chicago	11h 20m including layover	Find flight from$460
9:00 am — 10:00 pm	9:00 am — 11:50 am WN2968 Southwest Airlines New York — Houston 2h 40m stop 2:30 pm — 3:40 pm WN34 Southwest Airlines Houston — Dallas 3h 55m stop 7:35 pm — 10:00 pm WN2281 Southwest Airlines Dallas — Chicago	14h including layover	Find flight from$287
9:00 am — 10:00 pm	9:00 am — 11:50 am WN2968 Southwest Airlines New York — Houston 3h 50m stop 3:40 pm — 4:50 pm WN38 Southwest Airlines Houston — Dallas 2h 45m stop 7:35 pm — 10:00 pm WN2281 Southwest Airlines Dallas — Chicago	14h including layover	Find flight from$287
9:30 am — 2:50 pm	9:30 am — 11:10 am WN1580 Southwest Airlines New York — Lake Saint Louis 2h 35m stop 1:45 pm — 2:50 pm WN2328 Southwest Airlines Lake Saint Louis — Chicago	6h 20m including layover	Find flight from$394
9:30 am — 7:05 pm	9:30 am — 11:10 am WN1580 Southwest Airlines New York — Lake Saint Louis 6h 50m stop 6:00 pm — 7:05 pm WN4463 Southwest Airlines Lake Saint Louis — Chicago	10h 35m including layover	Find flight from$400

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

*Departure and arrival times are local. Last updated on 08/13/2025

Flight Information

There are 5 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 10:55 am to 9:30 am. Nonstop flight is 2h 20m. The time difference between New York and Chicago is 1h.

The fastest flight 2h 20m
Average flight time 2h 20m
The earliest flight 10:55 am
The latest flight 9:30 am
Distance 711 ml

The cheapest months for traveling to Chicago are august (from 244 $).

The cheapest flight by Southwest Airlines that our users were able to find is $244. This airfare is economy class on one-way WN3447 flight for August 9, 2025 leaving La Guardia in New York at 6:20 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:

Boeing 737 MAX 8

from $244

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Boeing 737-100/200

from $254

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Boeing 737-800

from $309

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Boeing 737

from $341

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Other Popular Airlines on the Route

Besides Southwest Airlines there are other 9 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 31 direct flights every day from New York. Airlines and fares are below:

B6 - JetBlue

from $226

Find
DL - Delta Air Lines Inc.

from $262

Find
UA - United Airlines

from $117

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NK - Spirit Airlines

from $57

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AA - American Airlines

from $301

Find

See more direct flights

Connecting Flights

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

B6 - JetBlue

from $536

Find
DL - Delta Air Lines Inc.

from $266

Find
UA - United Airlines

from $254

Find
NK - Spirit Airlines

from $168

Find
AA - American Airlines

from $271

Find
AS - Alaska Airlines

from $806

Find
F9 - Frontier Airlines

from $118

Find
EY - Etihad Airways

from $2684

Find
SY - Sun Country Airlines

from $376

Find

See more connecting flights

How to book an air ticket yourself?

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