Southwest Airlines
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Midway International Airport
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United States
San Diego International Airport
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Scan through all non-stop flights from Chicago to San Diego. The full flight schedule below gives an overview of all non-stop flights from MDW to SAN, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
The Mediterranean regions near San Diego are known for their warm, arid summers, where temperatures often go beyond 30°C (86°F). In some inland spots, the heat can climb even higher, sometimes reaching 40°C (104°F) or more. The winters are pleasantly mild, accompanied by some rainfall. This lovely climate, paired with breathtaking landscapes and bright, sunny days attract visitors from around the globe.
San Diego is a wonderful place to visit all year long, but spring (March-May) and fall (September-November) are the best seasons to visit. The weather is pleasantly warm during these times, especially since the summers can be quite hot in those regions.
Currently, there is only one airline operating non-stop flights from Chicago MDW to San Diego SAN, which is Southwest Airlines. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their MDW SAN flight schedule.
Flights from MDW to SAN are operated 24 times a week, with an average of 3 flights per day. Departure times vary between 05:30 - 21:10. The earliest flight departs at 05:30, the last flight departs at 21:10. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
On this non-stop route, you can fly in Economy only.
The fastest direct flight from Chicago to San Diego takes 4 hours and 5 minutes. The flight distance between Chicago and San Diego is 1,724 miles (or 2,775 km).
There are 2 airports in San Diego: San Diego International Airport (SAN) and McClellan-Palomar Airport (FAA: CRQ) (CLD).
There are 24 flights per week flying from Chicago to San Diego (as of April 2026).
4 hours and 5 minutes is the average flight time from Chicago to San Diego.
The distance from Chicago to San Diego is 1,724 miles (2,775 kilometers).
Southwest Airlines is the only airline flying nonstop from Chicago to San Diego.
There are no alliances flying direct from Chicago to San Diego at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Chicago to San Diego:
The earliest flight departs at 05:30 from Chicago and arrives at 07:50 at San Diego.
The latest flight departs at 21:10 from Chicago and arrives at 23:25 at San Diego.
1,724 miles (2,775 km) · 4h 5m
06:05
08:35
Southwest Airlines
WN 3994
Southwest Airlines
Boeing 757
Y
W
J
F
06:15
08:30
Southwest Airlines
WN 1357
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
06:40
08:55
Southwest Airlines
WN 1357
Southwest Airlines
Boeing 757
Y
W
J
F
06:45
09:00
Southwest Airlines
WN 1357
Southwest Airlines
Boeing 757
Y
W
J
F
10:00
12:30
Southwest Airlines
WN 2126
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:00
12:15
Southwest Airlines
WN 1186
Southwest Airlines
Boeing 757
Y
W
J
F
10:00
12:15
Southwest Airlines
WN 2305
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:05
12:35
Southwest Airlines
WN 2126
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:05
12:20
Southwest Airlines
WN 2305
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:10
12:40
Southwest Airlines
WN 2126
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
13:45
16:00
Southwest Airlines
WN 2072
Southwest Airlines
Boeing 757
Y
W
J
F
14:05
16:35
Southwest Airlines
WN 3994
Southwest Airlines
Boeing 757
Y
W
J
F
16:05
18:35
Southwest Airlines
WN 3996
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
17:15
19:35
Southwest Airlines
WN 3541
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
17:25
19:45
Southwest Airlines
WN 3541
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
18:10
20:30
Southwest Airlines
WN 3541
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
18:30
21:00
Southwest Airlines
WN 3996
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
20:45
23:10
Southwest Airlines
WN 3591
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
20:50
23:20
Southwest Airlines
WN 2972
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
20:55
23:25
Southwest Airlines
WN 2815
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
21:10
23:25
Southwest Airlines
WN 1357
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
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