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 $110 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 $110 | 9:15 am New York La Guardia | 10:50 am Chicago Midway | 2h 35m | Southwest Airlines | WN1634 |
from $110 | 11:10 am New York La Guardia | 12:40 pm Chicago Midway | 2h 30m | Southwest Airlines | WN2234 |
from $110 | 2:30 pm New York La Guardia | 4:00 pm Chicago Midway | 2h 30m | Southwest Airlines | WN2970 |
from $136 | 9:55 pm New York La Guardia | 11:20 pm Chicago Midway | 2h 25m | Southwest Airlines | WN1192 |
from $136 | 6:30 am New York La Guardia | 8:00 am Chicago Midway | 2h 30m | Southwest Airlines | WN761 |
from $137 | 4:45 pm New York La Guardia | 6:15 pm Chicago Midway | 2h 30m | Southwest Airlines | WN2468 |
from $137 | 6:55 pm New York La Guardia | 8:25 pm Chicago Midway | 2h 30m | Southwest Airlines | WN4246 |
from $148 | 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 $149 | 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 $155 | 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 $155 | 11:20 am New York La Guardia | 9:25 pm Chicago Midway | 11h 5m layover 6h 30m - Atlanta | Southwest Airlines | WN2174 WN4703 |
from $155 | 2:10 pm New York La Guardia | 10:20 pm Chicago Midway | 9h 10m layover 4h 55m - Nashville | Southwest Airlines | WN679 WN1647 |
from $155 | 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 $155 | 9:50 am New York La Guardia | 5:35 pm Chicago Midway | 8h 45m layover 4h 30m - Nashville | Southwest Airlines | WN1800 WN477 |
from $173 | 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 $211 | 7:20 am New York La Guardia | 11:50 am Chicago Midway | 5h 30m layover 1h 25m - Lake Saint Louis | Southwest Airlines | WN245 WN2364 |
Southwest Airlines Flight Schedule New York to Chicago
Departure | Arrival | 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$110 |
|
2:30 pm — 4:00 pm
|
2:30 pm — 4:00 pm
WN2970
Southwest Airlines
New York — Chicago
|
2h 30m |
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from$110 |
|
4:45 pm — 6:15 pm
|
4:45 pm — 6:15 pm
WN2468
Southwest Airlines
New York — Chicago
|
2h 30m |
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from$137 |
|
6:30 am — 8:00 am
|
6:30 am — 8:00 am
WN761
Southwest Airlines
New York — Chicago
|
2h 30m |
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from$136 |
|
6:55 pm — 8:25 pm
|
6:55 pm — 8:25 pm
WN4246
Southwest Airlines
New York — Chicago
|
2h 30m |
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from$137 |
|
9:15 am — 10:50 am
|
9:15 am — 10:50 am
WN1634
Southwest Airlines
New York — Chicago
|
2h 35m |
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from$110 |
|
9:55 pm — 11:20 pm
|
9:55 pm — 11:20 pm
WN1192
Southwest Airlines
New York — Chicago
|
2h 25m |
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from$136 |
|
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 |
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from$149 |
|
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 |
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from$149 |
|
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 |
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from$149 |
|
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 |
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from$155 |
|
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 |
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from$165 |
|
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 |
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from$156 |
|
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 |
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from$156 |
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 110 $).
The cheapest flight by Southwest Airlines that our users were able to find is $110. 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.
Southwest Airlines Airplanes on the Route
List of the most popular Southwest Airlines airplanes flying from New York to Chicago:
- Airbus A320from $110Find
- Boeing 737-800from $136Find
- Boeing 737 MAX 8from $137Find
- Boeing 737from $148Find
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 Airlinesfrom $70Find
Connecting Flights
List of flights with layovers (1 and more stops):
- from $949Find
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