Southwest Airlines New York to Chicago Flights
Cheapflightsplus.com will find cheap Southwest Airlines flights from New York to Chicago. Compare airline ticket prices and book air tickets starting from $48 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
Cheap Flights from New York to Chicago by Southwest Airlines
Price | Departure | Arrival | Flight Time | Airline | Flight |
---|---|---|---|---|---|
from $48 | 6:05 am New York La Guardia | 7:35 am Chicago Midway | 2h 30m | Southwest Airlines | WN3608 |
from $78 | 8:05 pm New York La Guardia | 9:45 pm Chicago Midway | 2h 40m | Southwest Airlines | WN3299 |
from $103 | 4:05 pm New York La Guardia | 5:40 pm Chicago Midway | 2h 35m | Southwest Airlines | WN3878 |
from $103 | 8:55 pm New York La Guardia | 10:25 pm Chicago Midway | 2h 30m | Southwest Airlines | WN1278 |
from $115 | 6:00 am New York La Guardia | 7:30 am Chicago Midway | 2h 30m | Southwest Airlines | WN1120 |
from $117 | 2:45 pm New York La Guardia | 4:15 pm Chicago Midway | 2h 30m | Southwest Airlines | WN4567 |
from $117 | 6:15 pm New York La Guardia | 7:55 pm Chicago Midway | 2h 40m | Southwest Airlines | WN3738 |
from $117 | 8:05 am New York La Guardia | 9:40 am Chicago Midway | 2h 35m | Southwest Airlines | WN3609 |
from $122 | 6:00 am New York La Guardia | 7:25 am Chicago Midway | 2h 25m | Southwest Airlines | WN3763 |
from $132 | 12:25 pm New York La Guardia | 2:00 pm Chicago Midway | 2h 35m | Southwest Airlines | WN1122 |
from $55 | 1:15 pm New York La Guardia | 5:30 pm Chicago Midway | 5h 15m layover 0h 45m - Atlanta | Southwest Airlines | WN2900 WN3613 |
from $55 | 2:20 pm New York La Guardia | 8:30 pm Chicago Midway | 7h 10m layover 0h 55m - Dallas | Southwest Airlines | WN4921 WN4495 |
Southwest Airlines Flight Schedule New York to Chicago
Departure | Arrival | Flight Details | Flight Time | Price |
---|---|---|---|---|
10:00 am — 11:45 am
|
10:00 am — 11:45 am
WN2263
Southwest Airlines
New York — Chicago
|
2h 45m |
Find flight
from$132 |
|
10:00 am — 11:40 am
|
10:00 am — 11:40 am
WN1426
Southwest Airlines
New York — Chicago
|
2h 40m |
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from$190 |
|
12:25 pm — 2:00 pm
|
12:25 pm — 2:00 pm
WN1122
Southwest Airlines
New York — Chicago
|
2h 35m |
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from$132 |
|
12:25 pm — 2:00 pm
|
12:25 pm — 2:00 pm
WN4369
Southwest Airlines
New York — Chicago
|
2h 35m |
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from$190 |
|
1:15 pm — 5:30 pm
|
1:15 pm — 3:50 pm
WN2900
Southwest Airlines
New York — Atlanta
45m stop
4:35 pm — 5:30 pm
WN3613
Southwest Airlines
Atlanta — Chicago
|
5h 15m including layover |
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from$55 |
|
2:20 pm — 8:30 pm
|
2:20 pm — 5:25 pm
WN4921
Southwest Airlines
New York — Dallas
55m stop
6:20 pm — 8:30 pm
WN4495
Southwest Airlines
Dallas — Chicago
|
7h 10m including layover |
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from$55 |
|
2:45 pm — 4:15 pm
|
2:45 pm — 4:15 pm
WN4567
Southwest Airlines
New York — Chicago
|
2h 30m |
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from$117 |
|
4:05 pm — 5:40 pm
|
4:05 pm — 5:40 pm
WN3878
Southwest Airlines
New York — Chicago
|
2h 35m |
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from$103 |
|
4:10 pm — 5:45 pm
|
4:10 pm — 5:45 pm
WN1537
Southwest Airlines
New York — Chicago
|
2h 35m |
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from$221 |
|
4:25 pm — 9:15 pm
|
4:25 pm — 7:00 pm
WN1682
Southwest Airlines
New York — Atlanta
1h 10m stop
8:10 pm — 9:15 pm
WN1898
Southwest Airlines
Atlanta — Chicago
|
5h 50m including layover |
Find flight
from$214 |
|
6:00 am — 7:30 am
|
6:00 am — 7:30 am
WN1120
Southwest Airlines
New York — Chicago
|
2h 30m |
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from$115 |
|
6:00 am — 7:25 am
|
6:00 am — 7:25 am
WN3763
Southwest Airlines
New York — Chicago
|
2h 25m |
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from$122 |
|
6:00 am — 7:25 am
|
6:00 am — 7:25 am
WN1165
Southwest Airlines
New York — Chicago
|
2h 25m |
Find flight
from$168 |
|
6:05 am — 7:35 am
|
6:05 am — 7:35 am
WN3608
Southwest Airlines
New York — Chicago
|
2h 30m |
Find flight
from$48 |
|
6:15 pm — 7:55 pm
|
6:15 pm — 7:55 pm
WN3738
Southwest Airlines
New York — Chicago
|
2h 40m |
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from$117 |
|
6:40 pm — 8:15 pm
|
6:40 pm — 8:15 pm
WN3776
Southwest Airlines
New York — Chicago
|
2h 35m |
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from$242 |
|
6:50 pm — 8:25 pm
|
6:50 pm — 8:25 pm
WN1124
Southwest Airlines
New York — Chicago
|
2h 35m |
Find flight
from$132 |
|
6:55 pm — 8:25 pm
|
6:55 pm — 8:25 pm
WN1463
Southwest Airlines
New York — Chicago
|
2h 30m |
Find flight
from$221 |
|
8:05 am — 9:40 am
|
8:05 am — 9:40 am
WN3609
Southwest Airlines
New York — Chicago
|
2h 35m |
Find flight
from$117 |
|
8:05 pm — 9:45 pm
|
8:05 pm — 9:45 pm
WN3299
Southwest Airlines
New York — Chicago
|
2h 40m |
Find flight
from$78 |
|
8:55 pm — 10:25 pm
|
8:55 pm — 10:25 pm
WN1278
Southwest Airlines
New York — Chicago
|
2h 30m |
Find flight
from$103 |
|
8:55 pm — 10:20 pm
|
8:55 pm — 10:20 pm
WN1284
Southwest Airlines
New York — Chicago
|
2h 25m |
Find flight
from$168 |
|
9:50 am — 11:25 am
|
9:50 am — 11:25 am
WN3876
Southwest Airlines
New York — Chicago
|
2h 35m |
Find flight
from$142 |
Flight Information
There are 20 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 10:00 am to 9:50 am. Nonstop flight is 2h 25m. The time difference between New York and Chicago is 1h.
- The fastest flight 2h 25m
- Average flight time 2h 35m
- The earliest flight 10:00 am
- The latest flight 9:50 am
- Distance 711 ml
The cheapest flight by Southwest Airlines that our users were able to find is $48. This airfare is economy class on one-way WN3608 flight for January 26, 2019 leaving La Guardia in New York at 6:05 am, it includes all taxes and additional fees.
Southwest Airlines Airplanes on the Route
List of the most popular Southwest Airlines airplanes flying from New York to Chicago:
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 24 direct flights every day from New York. Airlines and fares are below:
- from $57Find
- from $64Find
Connecting Flights
List of flights with layovers (1 and more stops):
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