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Southwest Airlines flights from San Diego to Chicago

Southwest Airlines flies San Diego to Chicago nonstop 11 times a week, departures from 06:15 to 08:35, 3h 50m in the air. Tickets from $154 (the route's cheapest fare is $133).

Flights from San Diego to Chicago

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Southwest Airlines on San Diego to Chicago at a glance

flights a week
11
days of operation
Daily
first and last departure
06:15 - 08:35
flight time
3h 50m - 7h 20m
aircraft
Boeing 737, Boeing 737-800
departure terminal
1
cheapest fare, 12 November
$154
cheapest fare on the route
$133

Southwest Airlines San Diego to Chicago schedule

11 flights a week. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
WN 1746
Southwest Airlines
06:15 San Diego International, terminal 1
12:10 Chicago Midway International
3h 55m
Sat
Boeing 737
WN 674
Southwest Airlines
06:30 San Diego International, terminal 1
12:30 Chicago Midway International
4h
Mon, Tue, Wed, Thu
Boeing 737
WN 3754
Southwest Airlines
06:35 San Diego International, terminal 1
12:35 Chicago Midway International
4h
Mon, Thu, Fri, Sun
Boeing 737-800
WN 1865
Southwest Airlines
08:30 San Diego International, terminal 1
15:40 Chicago Midway International
5h 10m
Sat
WN 1064
Southwest Airlines
08:35 San Diego International, terminal 1
17:45 Chicago Midway International
7h 10m
Sat

Seasonal and one-off flights

Not operating in the next two weeks. The first of them is on 24 November.

FlightDepartsArrivesDurationDaysAircraft
WN 3048
Southwest Airlines
06:40 San Diego International, terminal 1
12:40 Chicago Midway International
4h
Seasonal
WN 3048
Southwest Airlines
06:55 San Diego International, terminal 1
12:50 Chicago Midway International
3h 55m
Seasonal
Boeing 737
WN 634
Southwest Airlines
08:15 San Diego International, terminal 1
14:15 Chicago Midway International
4h
Seasonal
Boeing 737
WN 654
Southwest Airlines
06:40 San Diego International, terminal 1
12:35 Chicago Midway International
3h 55m
Seasonal
WN 3404
Southwest Airlines
07:40 San Diego International, terminal 1
13:30 Chicago Midway International
3h 50m
Seasonal
Boeing 737
WN 2687
Southwest Airlines
08:20 San Diego International, terminal 1
16:35 Chicago Midway International
6h 15m
Seasonal
WN 1772
Southwest Airlines
07:05 San Diego International, terminal 1
12:55 Chicago Midway International
3h 50m
Seasonal
Boeing 737
WN 1772
Southwest Airlines
06:35 San Diego International, terminal 1
12:30 Chicago Midway International
3h 55m
Seasonal
Boeing 737-800
WN 2553
Southwest Airlines
06:45 San Diego International, terminal 1
12:50 Chicago Midway International
4h 5m
Seasonal
WN 2901
Southwest Airlines
07:55 San Diego International, terminal 1
17:15 Chicago Midway International
7h 20m
Seasonal
Boeing 737-800
WN 2960
Southwest Airlines
06:15 San Diego International, terminal 1
12:30 Chicago Midway International
4h 15m
Seasonal
WN 2553
Southwest Airlines
07:00 San Diego International, terminal 1
13:05 Chicago Midway International
4h 5m
Seasonal
Boeing 737-800
WN 3718
Southwest Airlines
08:55 San Diego International, terminal 1
18:10 Chicago Midway International
7h 15m
Seasonal
WN 2046
Southwest Airlines
06:15 San Diego International, terminal 1
12:30 Chicago Midway International
4h 15m
Seasonal
Boeing 737
WN 1313
Southwest Airlines
06:15 San Diego International, terminal 1
12:30 Chicago Midway International
4h 15m
Seasonal
Boeing 737
WN 4285
Southwest Airlines
10:15 San Diego International, terminal 1
16:05 Chicago Midway International
3h 50m
Seasonal
Boeing 737
WN 4392
Southwest Airlines
06:50 San Diego International, terminal 1
12:50 Chicago Midway International
4h
Seasonal
Boeing 737-800
WN 4213
Southwest Airlines
06:15 San Diego International, terminal 1
12:30 Chicago Midway International
4h 15m
Seasonal
Boeing 737-800
WN 4762
Southwest Airlines
08:20 San Diego International, terminal 1
14:15 Chicago Midway International
3h 55m
Seasonal
Boeing 737
WN 2090
Southwest Airlines
06:30 San Diego International, terminal 1
12:30 Chicago Midway International
4h
Seasonal
Boeing 737-800
WN 4557
Southwest Airlines
06:15 San Diego International, terminal 1
12:40 Chicago Midway International
4h 25m
Seasonal
Boeing 737
WN 4557
Southwest Airlines
07:50 San Diego International, terminal 1
13:50 Chicago Midway International
4h
Seasonal
Boeing 737
WN 4557
Southwest Airlines
06:30 San Diego International, terminal 1
12:45 Chicago Midway International
4h 15m
Seasonal
WN 4544
Southwest Airlines
10:00 San Diego International, terminal 1
16:00 Chicago Midway International
4h
Seasonal
Boeing 737
WN 4557
Southwest Airlines
07:10 San Diego International, terminal 1
13:20 Chicago Midway International
4h 10m
Seasonal
Boeing 737
WN 4544
Southwest Airlines
10:25 San Diego International, terminal 1
16:25 Chicago Midway International
4h
Seasonal
Boeing 737

Days of the week are taken from the schedule for the next 14 days; schedules change by season. Chicago is 2 hours ahead of San Diego.

Other airlines flying San Diego to Chicago

Nonstop flights by the current schedule

American Airlines Alaska Airlines United Airlines All flights San Diego to Chicago

Frequently asked questions

How many Southwest Airlines flights are there from San Diego to Chicago?
11 nonstop flights a week, 24 flight numbers in the schedule: Daily.
How long is the Southwest Airlines flight from San Diego to Chicago?
From 3 hours 50 minutes to 7 hours 20 minutes nonstop, depending on the flight.
Which aircraft does Southwest Airlines fly from San Diego to Chicago?
Boeing 737 and Boeing 737-800.
Which terminals does Southwest Airlines use between San Diego and Chicago?
Southwest Airlines departs from San Diego International, terminal 1 and arrives at Chicago Midway International.
How much is a Southwest Airlines ticket from San Diego to Chicago?
The cheapest Southwest Airlines nonstop fare found recently is $154 for 12 November; the cheapest fare on the route with any airline is $133. The search shows the price for your date.