Southwest Airlines San Diego to Chicago Flights

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Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap Southwest Airlines flights from San Diego to Chicago. Compare airline ticket prices and book air tickets starting from $837 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 San Diego (CA) — 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 april: one-way - $837, two-way – $1435.

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Cheap Flights from San Diego 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 $837. The fastest nonstop flight takes 3h 55m. The fastest connecting flight — 5h 20m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $837 Find flight	3:25 pm San Diego San Diego	9:25 pm Chicago Midway	4h 0m	Southwest Airlines	WN4326
from $837 Find flight	7:15 pm San Diego San Diego	1:10 am+1 день Chicago Midway	3h 55m	Southwest Airlines	WN3581
from $856 Find flight	6:55 am San Diego San Diego	3:00 pm Chicago Midway	6h 5m	Southwest Airlines	WN2925
from $874 Find flight	11:15 am San Diego San Diego	8:15 pm Chicago Midway	7h 0m	Southwest Airlines	WN658
from $998 Find flight	9:00 am San Diego San Diego	5:30 pm Chicago Midway	6h 30m	Southwest Airlines	WN2564
from $1109 Find flight	10:45 am San Diego San Diego	4:40 pm Chicago Midway	3h 55m	Southwest Airlines	WN967
from $1173 Find flight	6:35 am San Diego San Diego	12:40 pm Chicago Midway	4h 5m	Southwest Airlines	WN3279
from $1488 Find flight	7:55 pm San Diego San Diego	1:55 am+1 день Chicago Midway	4h 0m	Southwest Airlines	WN270
from $1509 Find flight	3:20 pm San Diego San Diego	11:05 pm Chicago O'Hare International	5h 45m	Southwest Airlines	WN3208
from $2488 Find flight	10:25 am San Diego San Diego	4:25 pm Chicago Midway	4h 0m	Southwest Airlines	WN1544
from $873 Find flight	2:20 pm San Diego San Diego	9:45 pm Chicago Midway	5h 25m layover 0h 45m - Denver	Southwest Airlines	WN3056 WN1896
from $873 Find flight	5:00 pm San Diego San Diego	0:25 am+1 день Chicago Midway	5h 25m layover 0h 45m - Phoenix	Southwest Airlines	WN4926 WN3339

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 04/20/2024

Southwest Airlines Flight Schedule San Diego to Chicago

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
10:25 am — 4:25 pm	10:25 am — 4:25 pm WN1544 Southwest Airlines San Diego — Chicago	4h	Find flight from$2488
10:45 am — 4:40 pm	10:45 am — 4:40 pm WN967 Southwest Airlines San Diego — Chicago	3h 55m	Find flight from$1109
11:15 am — 8:15 pm	11:15 am — 8:15 pm WN658 Southwest Airlines San Diego — Chicago	7h	Find flight from$874
3:20 pm — 11:05 pm	3:20 pm — 11:05 pm WN3208 Southwest Airlines San Diego — Chicago	5h 45m	Find flight from$1509
3:25 pm — 9:25 pm	3:25 pm — 9:25 pm WN4326 Southwest Airlines San Diego — Chicago	4h	Find flight from$837
6:35 am — 12:40 pm	6:35 am — 12:40 pm WN3279 Southwest Airlines San Diego — Chicago	4h 5m	Find flight from$1173
6:55 am — 3:00 pm	6:55 am — 3:00 pm WN2925 Southwest Airlines San Diego — Chicago	6h 5m	Find flight from$856
7:15 pm — 1:10 am +1 day	7:15 pm — 1:10 am WN3581 Southwest Airlines San Diego — Chicago	3h 55m	Find flight from$837
7:55 pm — 1:55 am +1 day	7:55 pm — 1:55 am WN270 Southwest Airlines San Diego — Chicago	4h	Find flight from$1488
9:00 am — 5:30 pm	9:00 am — 5:30 pm WN2564 Southwest Airlines San Diego — Chicago	6h 30m	Find flight from$998
10:10 am — 7:40 pm	10:10 am — 1:30 pm WN2225 Southwest Airlines San Diego — Denver 2h 40m stop 4:10 pm — 7:40 pm WN3397 Southwest Airlines Denver — Chicago	7h 30m including layover	Find flight from$2433
11:10 am — 6:30 pm	11:10 am — 4:15 pm WN4045 Southwest Airlines San Diego — North Kansas City 50m stop 5:05 pm — 6:30 pm WN2630 Southwest Airlines North Kansas City — Chicago	5h 20m including layover	Find flight from$908
12:10 pm — 7:50 pm	12:10 pm — 1:30 pm WN2012 Southwest Airlines San Diego — Phoenix 1h stop 2:30 pm — 7:50 pm WN2970 Southwest Airlines Phoenix — Chicago	5h 40m including layover	Find flight from$1524
12:35 pm — 8:15 pm	12:35 pm — 6:10 pm WN3376 Southwest Airlines San Diego — Lake Saint Louis 1h stop 7:10 pm — 8:15 pm WN658 Southwest Airlines Lake Saint Louis — Chicago	5h 40m including layover	Find flight from$1209
1:10 pm — 8:55 pm	1:10 pm — 2:35 pm WN2675 Southwest Airlines San Diego — Phoenix 1h 5m stop 3:40 pm — 8:55 pm WN4124 Southwest Airlines Phoenix — Chicago	5h 45m including layover	Find flight from$873
1:30 pm — 11:05 pm	1:30 pm — 2:50 pm WN3059 Southwest Airlines San Diego — Phoenix 2h 40m stop 5:30 pm — 11:05 pm WN3208 Southwest Airlines Phoenix — Chicago	7h 35m including layover	Find flight from$1525
2:20 pm — 9:45 pm	2:20 pm — 5:35 pm WN3056 Southwest Airlines San Diego — Denver 45m stop 6:20 pm — 9:45 pm WN1896 Southwest Airlines Denver — Chicago	5h 25m including layover	Find flight from$873
3:00 pm — 11:10 pm	3:00 pm — 4:20 pm WN5494 Southwest Airlines San Diego — San Jose 45m stop 5:05 pm — 11:10 pm WN1870 Southwest Airlines San Jose — Chicago	6h 10m including layover	Find flight from$873
4:20 pm — 0:25 am +1 day	4:20 pm — 9:15 pm WN2932 Southwest Airlines San Diego — Austin 40m stop 9:55 pm — 0:25 am WN4442 Southwest Airlines Austin — Chicago	6h 5m including layover	Find flight from$873
4:55 pm — 1:00 am +1 day	4:55 pm — 6:20 pm WN2595 Southwest Airlines San Diego — Phoenix 1h 10m stop 7:30 pm — 1:00 am WN1644 Southwest Airlines Phoenix — Chicago	6h 5m including layover	Find flight from$1524
5:00 pm — 0:25 am +1 day	5:00 pm — 6:20 pm WN4926 Southwest Airlines San Diego — Phoenix 45m stop 7:05 pm — 0:25 am WN3339 Southwest Airlines Phoenix — Chicago	5h 25m including layover	Find flight from$873
5:20 pm — 1:20 am +1 day	5:20 pm — 8:45 pm WN2752 Southwest Airlines San Diego — Denver 1h 15m stop 10:00 pm — 1:20 am WN425 Southwest Airlines Denver — Chicago	6h including layover	Find flight from$1524
6:25 am — 2:15 pm	6:25 am — 7:45 am WN670 Southwest Airlines San Diego — Las Vegas 1h stop 8:45 am — 2:15 pm WN2984 Southwest Airlines Las Vegas — Chicago	5h 50m including layover	Find flight from$1145
8:55 am — 4:35 pm	8:55 am — 10:15 am WN3042 Southwest Airlines San Diego — Phoenix 1h 5m stop 11:20 am — 4:35 pm WN2821 Southwest Airlines Phoenix — Chicago	5h 40m including layover	Find flight from$908
9:00 am — 4:25 pm	9:00 am — 10:20 am WN3273 Southwest Airlines San Diego — Phoenix 55m stop 11:15 am — 4:25 pm WN6590 Southwest Airlines Phoenix — Chicago	5h 25m including layover	Find flight from$1524

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

*Departure and arrival times are local. Last updated on 04/20/2024

Flight Information

There are 10 flights by Southwest Airlines from San Diego to Chicago every week with departures from San Diego, AFB, Golden Triangle Reg., Lowndes County, San Diego Regional, El Cajon, Montgomery Field, Miramar NAS, North Island NAS, Brown Field Municipal, Gillespie Field. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 10:10 am to 9:10 am. Nonstop flight is 3h 55m. The time difference between San Diego and Chicago is 2h.

The fastest flight 3h 55m
Average flight time 4h 3m
The earliest flight 10:10 am
The latest flight 9:10 am
Distance 1733 ml

The cheapest months for traveling to Chicago are august (from 837 $).

The cheapest flight by Southwest Airlines that our users were able to find is $837. This airfare is economy class on one-way WN4326 flight for August 31, 2023 leaving San Diego in San Diego at 3:25 pm, 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 San Diego to Chicago:

Boeing 737-100/200

from $837

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Other Popular Airlines on the Route

Besides Southwest Airlines there are other 8 airline carriers between San Diego and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from San Diego to Chicago.

Nonstop flights

There are 22 direct flights every day from San Diego. Airlines and fares are below:

AA - American Airlines

from $610

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AS - Alaska Airlines

from $973

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UA - United Airlines

from $567

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Connecting Flights

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

AA - American Airlines

from $557

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AS - Alaska Airlines

from $572

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F9 - Frontier Airlines

from $319

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SY - Sun Country Airlines

from $1207

Find
DL - Delta Air Lines Inc.

from $561

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UA - United Airlines

from $564

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NK - Spirit Airlines

from $287

Find
G4 - Allegiant Air

from $374

Find

See more connecting flights

How to book an air ticket yourself?

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