Southwest Airlines Chicago to New York Flights

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Cheapflightsplus.com will find cheap Southwest Airlines flights from Chicago to New York. Compare airline ticket prices and book air tickets starting from $94 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 september: one-way - $94, two-way – $161.

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Cheap Flights from Chicago to New York 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 $94. The fastest nonstop flight takes 2h. The fastest connecting flight — 4h 55m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $94 Find flight	6:00 am Chicago Midway	9:05 am New York La Guardia	2h 5m	Southwest Airlines	WN447
from $94 Find flight	7:55 pm Chicago Midway	11:00 pm New York La Guardia	2h 5m	Southwest Airlines	WN533
from $120 Find flight	8:35 am Chicago Midway	11:40 am New York La Guardia	2h 5m	Southwest Airlines	WN2109
from $120 Find flight	2:25 pm Chicago Midway	5:25 pm New York La Guardia	2h 0m	Southwest Airlines	WN2860
from $120 Find flight	5:50 pm Chicago Midway	9:00 pm New York La Guardia	2h 10m	Southwest Airlines	WN1737
from $120 Find flight	1:10 pm Chicago Midway	4:10 pm New York La Guardia	2h 0m	Southwest Airlines	WN2165
from $120 Find flight	11:45 am Chicago Midway	2:45 pm New York La Guardia	2h 0m	Southwest Airlines	WN4031
from $135 Find flight	5:00 pm Chicago Midway	11:05 pm New York La Guardia	5h 5m layover 1h 30m - Lake Saint Louis	Southwest Airlines	WN2962 WN4161
from $135 Find flight	11:15 am Chicago Midway	8:00 pm New York La Guardia	7h 45m layover 3h 35m - North Kansas City	Southwest Airlines	WN2814 WN1451
from $135 Find flight	3:25 pm Chicago Midway	10:55 pm New York La Guardia	6h 30m layover 2h 25m - Atlanta	Southwest Airlines	WN3272 WN4463
from $135 Find flight	6:20 am Chicago Midway	2:55 pm New York La Guardia	7h 35m layover 3h 40m - Nashville	Southwest Airlines	WN2665 WN1932
from $135 Find flight	1:00 pm Chicago Midway	9:10 pm New York La Guardia	7h 10m layover 3h 40m - Lake Saint Louis	Southwest Airlines	WN2602 WN3736
from $135 Find flight	7:15 am Chicago Midway	1:25 pm New York La Guardia	5h 10m layover 1h 30m - Lake Saint Louis	Southwest Airlines	WN794 WN1591
from $135 Find flight	9:00 am Chicago Midway	2:55 pm New York La Guardia	4h 55m layover 1h 5m - Nashville	Southwest Airlines	WN3219 WN1932
from $135 Find flight	1:30 pm Chicago Midway	8:00 pm New York La Guardia	5h 30m layover 1h 45m - Nashville	Southwest Airlines	WN2993 WN3484
from $142 Find flight	1:00 pm Chicago Midway	11:05 pm New York La Guardia	9h 5m layover 5h 35m - Lake Saint Louis	Southwest Airlines	WN2602 WN4161

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 09/07/2025

Southwest Airlines Flight Schedule Chicago to New York

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
11:15 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	Find flight from$135
11:45 am — 2:45 pm	11:45 am — 2:45 pm WN4031 Southwest Airlines Chicago — New York	2h	Find flight from$120
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	Find flight from$135
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	Find flight from$142
1:10 pm — 4:10 pm	1:10 pm — 4:10 pm WN2165 Southwest Airlines Chicago — New York	2h	Find flight from$120
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	Find flight from$135
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	Find flight from$142
2:25 pm — 5:25 pm	2:25 pm — 5:25 pm WN2860 Southwest Airlines Chicago — New York	2h	Find flight from$120
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	Find flight from$135
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$135
5:50 pm — 9:00 pm	5:50 pm — 9:00 pm WN1737 Southwest Airlines Chicago — New York	2h 10m	Find flight from$120
6:00 am — 9:05 am	6:00 am — 9:05 am WN447 Southwest Airlines Chicago — New York	2h 5m	Find flight from$94
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	Find flight from$135
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$135
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	Find flight from$142
7:55 pm — 11:00 pm	7:55 pm — 11:00 pm WN533 Southwest Airlines Chicago — New York	2h 5m	Find flight from$94
8:35 am — 11:40 am	8:35 am — 11:40 am WN2109 Southwest Airlines Chicago — New York	2h 5m	Find flight from$120
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$135
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$142

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

*Departure and arrival times are local. Last updated on 09/07/2025

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 94 $).

The cheapest flight by Southwest Airlines that our users were able to find is $94. 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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Southwest Airlines Airplanes on the Route

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

Airbus A320

from $94

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Boeing 737 MAX 8

from $135

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Boeing 737-700

from $135

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Boeing 737-800

from $135

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Other Popular Airlines on the Route

Besides Southwest Airlines there are other 7 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 20 direct flights every day from Chicago. Airlines and fares are below:

UA - United Airlines

from $109

Find
NK - Spirit Airlines

from $55

Find

See more direct flights

Connecting Flights

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

UA - United Airlines

from $153

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NK - Spirit Airlines

from $109

Find
AS - Alaska Airlines

from $325

Find
F9 - Frontier Airlines

from $109

Find
SY - Sun Country Airlines

from $331

Find
AY - Finnair

from $3131

Find
HA - Hawaiian Airlines

from $805

Find

See more connecting flights

How to book an air ticket yourself?

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