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 $78 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 may: one-way - $78, two-way – $134.

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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 $78. The fastest nonstop flight takes 2h 5m. The fastest connecting flight — 4h 54m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $78 Find flight	6:05 am Chicago Midway	9:10 am New York La Guardia	2h 5m	Southwest Airlines	WN2021
from $78 Find flight	8:15 pm Chicago Midway	11:25 pm New York La Guardia	2h 10m	Southwest Airlines	WN2217
from $84 Find flight	5:10 pm Chicago Midway	8:20 pm New York La Guardia	2h 10m	Southwest Airlines	WN4672
from $84 Find flight	2:45 pm Chicago Midway	5:55 pm New York La Guardia	2h 10m	Southwest Airlines	WN356
from $97 Find flight	12:20 pm Chicago Midway	3:30 pm New York La Guardia	2h 10m	Southwest Airlines	WN2023
from $97 Find flight	8:10 am Chicago Midway	11:15 am New York La Guardia	2h 5m	Southwest Airlines	WN354
from $131 Find flight	10:30 pm Chicago Midway	7:30 am+1 день New York La Guardia	8h 0m layover 4h 20m - Boston	Southwest Airlines	WN2251 DL524
from $138 Find flight	5:00 am Chicago Midway	12:28 pm New York John F Kennedy Intl	6h 28m layover 2h 50m - Boston	Southwest Airlines	WN2417 DL3963
from $148 Find flight	10:30 pm Chicago Midway	7:25 am+1 день New York John F Kennedy Intl	7h 55m layover 4h 20m - Boston	Southwest Airlines	WN2251 DL5070
from $158 Find flight	8:25 am Chicago Midway	3:37 pm New York John F Kennedy Intl	6h 12m layover 2h 30m - Raleigh	Southwest Airlines	WN2249 DL3365
from $172 Find flight	10:00 pm Chicago Midway	7:26 am+1 день New York La Guardia	8h 26m layover 5h 35m - Buffalo	Southwest Airlines	WN2319 DL5427
from $162 Find flight	5:30 am Chicago Midway	2:10 pm New York John F Kennedy Intl	7h 40m layover 1h 0m - Baltimore 2h 10m - Buffalo	Southwest Airlines	WN1065 WN2296 DL5136

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 04/25/2024

Southwest Airlines Flight Schedule Chicago to New York

Below is a detailed 2024 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
12:20 pm — 3:30 pm	12:20 pm — 3:30 pm WN2023 Southwest Airlines Chicago — New York	2h 10m	Find flight from$97
2:45 pm — 5:55 pm	2:45 pm — 5:55 pm WN356 Southwest Airlines Chicago — New York	2h 10m	Find flight from$84
5:10 pm — 8:20 pm	5:10 pm — 8:20 pm WN4672 Southwest Airlines Chicago — New York	2h 10m	Find flight from$84
6:05 am — 9:10 am	6:05 am — 9:10 am WN2021 Southwest Airlines Chicago — New York	2h 5m	Find flight from$78
8:10 am — 11:15 am	8:10 am — 11:15 am WN354 Southwest Airlines Chicago — New York	2h 5m	Find flight from$97
8:15 pm — 11:25 pm	8:15 pm — 11:25 pm WN2217 Southwest Airlines Chicago — New York	2h 10m	Find flight from$78
10:30 pm — 7:30 am +1 day	10:30 pm — 1:40 am WN2251 Southwest Airlines Chicago — Boston 4h 20m stop 6:00 am — 7:30 am DL524 Delta Air Lines Inc. Boston — New York	8h including layover	Find flight from$131
10:30 pm — 7:25 am +1 day	10:30 pm — 1:40 am WN2251 Southwest Airlines Chicago — Boston 4h 20m stop 6:00 am — 7:25 am DL5070 Delta Air Lines Inc. Boston — New York	7h 55m including layover	Find flight from$148
11:15 am — 6:40 pm	11:15 am — 2:30 pm WN872 Southwest Airlines Chicago — Boston 2h 30m stop 5:00 pm — 6:40 pm DL1707 Delta Air Lines Inc. Boston — New York	6h 25m including layover	Find flight from$184
11:50 am — 7:54 pm	11:50 am — 2:45 pm WN1782 Southwest Airlines Chicago — Atlanta 2h 20m stop 5:05 pm — 7:54 pm DL2021 Delta Air Lines Inc. Atlanta — New York	7h 4m including layover	Find flight from$211
12:20 pm — 8:09 pm	12:20 pm — 3:20 pm WN2016 Southwest Airlines Chicago — Charlotte 2h 35m stop 5:55 pm — 8:09 pm DL725 Delta Air Lines Inc. Charlotte — New York	6h 49m including layover	Find flight from$230
1:45 pm — 10:24 pm	1:45 pm — 5:20 pm WN1763 Southwest Airlines Chicago — Tampa 2h 10m stop 7:30 pm — 10:24 pm DL1267 Delta Air Lines Inc. Tampa — New York	7h 39m including layover	Find flight from$221
1:55 pm — 8:15 pm	1:55 pm — 4:30 pm WN2503 Southwest Airlines Chicago — Buffalo 2h 7m stop 6:37 pm — 8:15 pm DL5311 Delta Air Lines Inc. Buffalo — New York	5h 20m including layover	Find flight from$247
2:25 pm — 5:51 am +1 day	2:25 pm — 4:00 pm WN794 Southwest Airlines Chicago — Denver 7h 59m stop 11:59 pm — 5:51 am DL2328 Delta Air Lines Inc. Denver — New York	14h 26m including layover	Find flight from$183
3:00 pm — 0:22 am +1 day	3:00 pm — 6:05 pm WN107 Southwest Airlines Chicago — Atlanta 3h 40m stop 9:45 pm — 0:22 am DL1888 Delta Air Lines Inc. Atlanta — New York	8h 22m including layover	Find flight from$220
5:00 am — 12:28 pm	5:00 am — 8:15 am WN2417 Southwest Airlines Chicago — Boston 2h 50m stop 11:05 am — 12:28 pm DL3963 Delta Air Lines Inc. Boston — New York	6h 28m including layover	Find flight from$138
6:10 am — 2:57 pm	6:10 am — 9:40 am WN485 Southwest Airlines Chicago — Orlando 2h 38m stop 12:18 pm — 2:57 pm DL2788 Delta Air Lines Inc. Orlando — New York	7h 47m including layover	Find flight from$184
9:00 am — 5:43 pm	9:00 am — 11:10 am WN2398 Southwest Airlines Chicago — Detroit 4h 30m stop 3:40 pm — 5:43 pm DL422 Delta Air Lines Inc. Detroit — New York	7h 43m including layover	Find flight from$228
9:30 am — 6:18 pm	9:30 am — 1:00 pm WN1099 Southwest Airlines Chicago — Orlando 2h 25m stop 3:25 pm — 6:18 pm DL1473 Delta Air Lines Inc. Orlando — New York	7h 48m including layover	Find flight from$220
7:00 am — 2:58 pm	7:00 am — 9:05 am WN882 Southwest Airlines Chicago — Covington 2h 25m stop 11:30 am — 1:02 pm DL3486 Delta Air Lines Inc. Covington — Baltimore 42m stop 1:44 pm — 2:58 pm DL5189 Delta Air Lines Inc. Baltimore — New York	6h 58m including layover	Find flight from$226
7:30 am — 6:39 pm	7:30 am — 9:05 am WN2468 Southwest Airlines Chicago — Denver 2h 8m stop 11:13 am — 2:11 pm DL1708 Delta Air Lines Inc. Denver — Minneapolis 30m stop 2:41 pm — 6:39 pm DL106 Delta Air Lines Inc. Minneapolis — New York	10h 9m including layover	Find flight from$182

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

*Departure and arrival times are local. Last updated on 04/25/2024

Flight Information

There are 6 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 10:00 pm to 9:30 am. Nonstop flight is 2h 5m. The time difference between Chicago and New York is 1h.

The fastest flight 2h 5m
Average flight time 2h 10m
The earliest flight 10:00 pm
The latest flight 9:30 am
Distance 711 ml

The cheapest flight by Southwest Airlines that our users were able to find is $78. This airfare is economy class on one-way WN2021 flight for July 10, 2019 leaving Midway in Chicago at 6:05 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:

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 6 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):

AA - American Airlines

from $186

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How to book an air ticket yourself?

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