Southwest Airlines Chicago to San Diego Flights

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Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap Southwest Airlines flights from Chicago to San Diego. Compare airline ticket prices and book air tickets starting from $1 353 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) — San Diego (CA) 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 march: one-way - $1353, two-way – $2320.

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Cheap Flights from Chicago to San Diego 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 $1 353. The fastest nonstop flight takes 4h. The fastest connecting flight — 5h 20m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $1353 Find flight	10:45 am Chicago Midway	12:50 pm San Diego San Diego	4h 5m	Southwest Airlines	WN1802
from $1353 Find flight	5:20 am Chicago Midway	7:20 am San Diego San Diego	4h 0m	Southwest Airlines	WN3166
from $1353 Find flight	9:20 pm Chicago Midway	11:20 pm San Diego San Diego	4h 0m	Southwest Airlines	WN3012
from $1372 Find flight	7:15 pm Chicago Midway	10:40 pm San Diego San Diego	5h 25m	Southwest Airlines	WN1323
from $1389 Find flight	12:00 pm Chicago Midway	5:35 pm San Diego San Diego	7h 35m	Southwest Airlines	WN2132
from $2300 Find flight	2:10 pm Chicago Midway	4:10 pm San Diego San Diego	4h 0m	Southwest Airlines	WN2475
from $1374 Find flight	7:20 am Chicago Midway	11:15 am San Diego San Diego	5h 55m layover 1h 0m - Las Vegas	Southwest Airlines	WN2916 WN2682
from $1374 Find flight	5:35 am Chicago Midway	9:15 am San Diego San Diego	5h 40m layover 0h 50m - Denver	Southwest Airlines	WN1818 WN3155
from $1374 Find flight	3:15 pm Chicago Midway	6:55 pm San Diego San Diego	5h 40m layover 1h 15m - North Kansas City	Southwest Airlines	WN146 WN3420
from $1374 Find flight	5:05 pm Chicago Midway	9:00 pm San Diego San Diego	5h 55m layover 1h 15m - Phoenix	Southwest Airlines	WN6531 WN1219
from $1374 Find flight	2:00 pm Chicago Midway	5:20 pm San Diego San Diego	5h 20m layover 0h 45m - Phoenix	Southwest Airlines	WN2360 WN3490
from $1374 Find flight	2:00 pm Chicago Midway	5:55 pm San Diego San Diego	5h 55m layover 1h 5m - Las Vegas	Southwest Airlines	WN3040 WN2219
from $1374 Find flight	12:15 pm Chicago Midway	4:15 pm San Diego San Diego	6h 0m layover 1h 25m - Phoenix	Southwest Airlines	WN2702 WN920
from $1374 Find flight	6:30 pm Chicago Midway	10:15 pm San Diego San Diego	5h 45m layover 1h 0m - Lake Saint Louis	Southwest Airlines	WN915 WN6505
from $1374 Find flight	9:20 am Chicago Midway	1:20 pm San Diego San Diego	6h 0m layover 1h 20m - Phoenix	Southwest Airlines	WN570 WN3262
from $1374 Find flight	3:30 pm Chicago Midway	7:25 pm San Diego San Diego	5h 55m layover 1h 5m - Las Vegas	Southwest Airlines	WN2941 WN716

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 03/14/2025

Southwest Airlines Flight Schedule Chicago to San Diego

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
10:45 am — 12:50 pm	10:45 am — 12:50 pm WN1802 Southwest Airlines Chicago — San Diego	4h 5m	Find flight from$1353
12:00 pm — 5:35 pm	12:00 pm — 5:35 pm WN2132 Southwest Airlines Chicago — San Diego	7h 35m	Find flight from$1389
12:15 pm — 4:15 pm	12:15 pm — 1:45 pm WN2702 Southwest Airlines Chicago — Phoenix 1h 25m stop 3:10 pm — 4:15 pm WN920 Southwest Airlines Phoenix — San Diego	6h including layover	Find flight from$1374
12:55 pm — 6:25 pm	12:55 pm — 6:25 pm WN212 Southwest Airlines Chicago — San Diego	7h 30m	Find flight from$2336
2:00 pm — 5:20 pm	2:00 pm — 3:30 pm WN2360 Southwest Airlines Chicago — Phoenix 45m stop 4:15 pm — 5:20 pm WN3490 Southwest Airlines Phoenix — San Diego	5h 20m including layover	Find flight from$1374
2:00 pm — 5:55 pm	2:00 pm — 3:40 pm WN3040 Southwest Airlines Chicago — Las Vegas 1h 5m stop 4:45 pm — 5:55 pm WN2219 Southwest Airlines Las Vegas — San Diego	5h 55m including layover	Find flight from$1374
2:10 pm — 4:10 pm	2:10 pm — 4:10 pm WN2475 Southwest Airlines Chicago — San Diego	4h	Find flight from$2300
3:15 pm — 6:55 pm	3:15 pm — 4:35 pm WN146 Southwest Airlines Chicago — North Kansas City 1h 15m stop 5:50 pm — 6:55 pm WN3420 Southwest Airlines North Kansas City — San Diego	5h 40m including layover	Find flight from$1374
3:30 pm — 7:25 pm	3:30 pm — 5:15 pm WN2941 Southwest Airlines Chicago — Las Vegas 1h 5m stop 6:20 pm — 7:25 pm WN716 Southwest Airlines Las Vegas — San Diego	5h 55m including layover	Find flight from$1374
5:05 pm — 9:00 pm	5:05 pm — 6:35 pm WN6531 Southwest Airlines Chicago — Phoenix 1h 15m stop 7:50 pm — 9:00 pm WN1219 Southwest Airlines Phoenix — San Diego	5h 55m including layover	Find flight from$1374
5:20 am — 7:20 am	5:20 am — 7:20 am WN3166 Southwest Airlines Chicago — San Diego	4h	Find flight from$1353
5:35 am — 9:15 am	5:35 am — 7:10 am WN1818 Southwest Airlines Chicago — Denver 50m stop 8:00 am — 9:15 am WN3155 Southwest Airlines Denver — San Diego	5h 40m including layover	Find flight from$1374
6:30 pm — 10:15 pm	6:30 pm — 7:35 pm WN915 Southwest Airlines Chicago — Lake Saint Louis 1h stop 8:35 pm — 10:15 pm WN6505 Southwest Airlines Lake Saint Louis — San Diego	5h 45m including layover	Find flight from$1374
7:15 pm — 10:40 pm	7:15 pm — 10:40 pm WN1323 Southwest Airlines Chicago — San Diego	5h 25m	Find flight from$1372
7:20 am — 11:15 am	7:20 am — 9:05 am WN2916 Southwest Airlines Chicago — Las Vegas 1h stop 10:05 am — 11:15 am WN2682 Southwest Airlines Las Vegas — San Diego	5h 55m including layover	Find flight from$1374
9:20 am — 1:20 pm	9:20 am — 10:55 am WN570 Southwest Airlines Chicago — Phoenix 1h 20m stop 12:15 pm — 1:20 pm WN3262 Southwest Airlines Phoenix — San Diego	6h including layover	Find flight from$1374
9:20 pm — 11:20 pm	9:20 pm — 11:20 pm WN3012 Southwest Airlines Chicago — San Diego	4h	Find flight from$1353

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

*Departure and arrival times are local. Last updated on 03/14/2025

Flight Information

There are 7 flights by Southwest Airlines from Chicago to San Diego 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 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.

Departures start from 10:45 am to 9:20 pm. Nonstop flight is 4h. The time difference between Chicago and San Diego is 2h.

The fastest flight 4h
Average flight time 4h 5m
The earliest flight 10:45 am
The latest flight 9:20 pm
Distance 1733 ml

The cheapest flight by Southwest Airlines that our users were able to find is $1 353. This airfare is economy class on one-way WN1802 flight for August 14, 2023 leaving Midway in Chicago at 10:45 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 San Diego:

Boeing 737-100/200

from $1 353

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Other Popular Airlines on the Route

Besides Southwest Airlines there are other 7 airline carriers between Chicago and San Diego. Please review schedules and prices from the most popular airlines to find the best airfare deals from Chicago to San Diego.

Nonstop flights

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

UA - United Airlines

from $317

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AS - Alaska Airlines

from $372

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Connecting Flights

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

UA - United Airlines

from $241

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AS - Alaska Airlines

from $185

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F9 - Frontier Airlines

from $62

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PD - Porter Airlines

from $446

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SY - Sun Country Airlines

from $128

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NK - Spirit Airlines

from $85

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TS - Air Transat

from $479

Find

See more connecting flights

How to book an air ticket yourself?

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That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
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