Southwest Airlines San Diego to Chicago Flights

One way Round trip

Adults

Children under 12

Infants under 2 without place

Economy

Business

First

done

Return flight: Chicago – San Diego

Page navigation

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 $879 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 march: one-way - $879, two-way – $1507.

Direct flights

Check to choose departure date Check to choose departure date

Check prices for return flight

Find flights

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 $879. The fastest nonstop flight takes 3h 55m. The fastest connecting flight — 5h 20m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $879 Find flight	3:25 pm San Diego San Diego	9:25 pm Chicago Midway	4h 0m	Southwest Airlines	WN4326
from $879 Find flight	7:15 pm San Diego San Diego	1:10 am+1 день Chicago Midway	3h 55m	Southwest Airlines	WN3581
from $899 Find flight	6:55 am San Diego San Diego	3:00 pm Chicago Midway	6h 5m	Southwest Airlines	WN2925
from $917 Find flight	11:15 am San Diego San Diego	8:15 pm Chicago Midway	7h 0m	Southwest Airlines	WN658
from $1048 Find flight	9:00 am San Diego San Diego	5:30 pm Chicago Midway	6h 30m	Southwest Airlines	WN2564
from $1231 Find flight	6:35 am San Diego San Diego	12:40 pm Chicago Midway	4h 5m	Southwest Airlines	WN3279
from $1561 Find flight	7:55 pm San Diego San Diego	1:55 am+1 день Chicago Midway	4h 0m	Southwest Airlines	WN270
from $2611 Find flight	10:25 am San Diego San Diego	4:25 pm Chicago Midway	4h 0m	Southwest Airlines	WN1544
from $916 Find flight	3:10 pm San Diego San Diego	11:15 pm Chicago Midway	6h 5m layover 1h 20m - Las Vegas	Southwest Airlines	WN1791 WN894
from $916 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 $916 Find flight	3:00 pm San Diego San Diego	11:10 pm Chicago Midway	6h 10m layover 0h 45m - San Jose	Southwest Airlines	WN5494 WN1870
from $916 Find flight	4:20 pm San Diego San Diego	0:25 am+1 день Chicago Midway	6h 5m layover 0h 40m - Austin	Southwest Airlines	WN2932 WN4442
from $916 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
from $916 Find flight	1:10 pm San Diego San Diego	8:55 pm Chicago Midway	5h 45m layover 1h 5m - Phoenix	Southwest Airlines	WN2675 WN4124
from $1201 Find flight	6:25 am San Diego San Diego	2:15 pm Chicago Midway	5h 50m layover 1h 0m - Las Vegas	Southwest Airlines	WN670 WN2984
from $1599 Find flight	4:55 pm San Diego San Diego	1:00 am+1 день Chicago Midway	6h 5m layover 1h 10m - Phoenix	Southwest Airlines	WN2595 WN1644

Show All Flights

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

Southwest Airlines Flight Schedule San Diego to Chicago

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
10:25 am — 4:25 pm	10:25 am — 4:25 pm WN1544 Southwest Airlines San Diego — Chicago	4h	Find flight from$2611
10:45 am — 4:40 pm	10:45 am — 4:40 pm WN967 Southwest Airlines San Diego — Chicago	3h 55m	Find flight from$1164
11:15 am — 8:15 pm	11:15 am — 8:15 pm WN658 Southwest Airlines San Diego — Chicago	7h	Find flight from$917
3:20 pm — 11:05 pm	3:20 pm — 11:05 pm WN3208 Southwest Airlines San Diego — Chicago	5h 45m	Find flight from$1583
3:25 pm — 9:25 pm	3:25 pm — 9:25 pm WN4326 Southwest Airlines San Diego — Chicago	4h	Find flight from$879
6:35 am — 12:40 pm	6:35 am — 12:40 pm WN3279 Southwest Airlines San Diego — Chicago	4h 5m	Find flight from$1231
6:55 am — 3:00 pm	6:55 am — 3:00 pm WN2925 Southwest Airlines San Diego — Chicago	6h 5m	Find flight from$899
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$879
7:55 pm — 1:55 am +1 day	7:55 pm — 1:55 am WN270 Southwest Airlines San Diego — Chicago	4h	Find flight from$1561
9:00 am — 5:30 pm	9:00 am — 5:30 pm WN2564 Southwest Airlines San Diego — Chicago	6h 30m	Find flight from$1048
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$2554
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$953
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$1599
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$1268
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$916
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$1600
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$916
3:10 pm — 11:15 pm	3:10 pm — 4:25 pm WN1791 Southwest Airlines San Diego — Las Vegas 1h 20m stop 5:45 pm — 11:15 pm WN894 Southwest Airlines Las Vegas — Chicago	6h 5m including layover	Find flight from$916
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$916
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$1599
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$916
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$1599
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$1201
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$953
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$1599

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 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 flight by Southwest Airlines that our users were able to find is $879. 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.

Find same flight?

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 $879

Find

Other Popular Airlines on the Route

Besides Southwest Airlines there are other 5 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 23 direct flights every day from San Diego. Airlines and fares are below:

UA - United Airlines

from $318

Find
AS - Alaska Airlines

from $373

Find

See more direct flights

Connecting Flights

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

UA - United Airlines

from $226

Find
AS - Alaska Airlines

from $187

Find
F9 - Frontier Airlines

from $59

Find
SY - Sun Country Airlines

from $128

Find
NK - Spirit Airlines

from $37

Find

See more connecting flights

How to book an air ticket yourself?

Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
Click «Buy» when you are ready — our system will redirect you to the site that sells the selected airfare.
Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
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.
To find a plane ticket, please select dates.