Southwest Airlines
Did you mean flights from Chicago to San Diego?
United States
San Diego International Airport
Switch direction
United States
Midway International Airport
Click to show full flight schedule
Scan through all non-stop flights from San Diego to Chicago. The full flight schedule below gives an overview of all non-stop flights from SAN to MDW, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
Currently, there is only one airline operating non-stop flights from San Diego SAN to Chicago MDW, 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 SAN MDW flight schedule.
Flights from SAN to MDW are operated 23 times a week, with an average of 3 flights per day. Departure times vary between 06:15 - 22:40. The earliest flight departs at 06:15, the last flight departs at 22:40. 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 San Diego to Chicago takes 4 hours. The flight distance between San Diego and Chicago is 1,724 miles (or 2,775 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 23 flights per week flying from San Diego to Chicago (as of October 2026).
4 hours is the average flight time from San Diego to Chicago.
The distance from San Diego to Chicago is 1,724 miles (2,775 kilometers).
Southwest Airlines is the only airline flying nonstop from San Diego to Chicago.
There are no alliances flying direct from San Diego to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from San Diego to Chicago:
The earliest flight departs at 06:15 from San Diego and arrives at 12:10 at Chicago.
The latest flight departs at 22:40 from San Diego and arrives at 04:30 at Chicago.
1,724 miles (2,775 km) · 4h
06:15
12:10
Southwest Airlines
WN 4237
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
06:15
12:10
Southwest Airlines
WN 2772
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
06:30
12:20
Southwest Airlines
WN 1785
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
06:40
12:30
Southwest Airlines
WN 2452
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
11:15
17:05
Southwest Airlines
WN 3370
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
11:55
17:45
Southwest Airlines
WN 1252
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
12:20
18:10
Southwest Airlines
WN 2453
Southwest Airlines
Boeing 737-700
Y
W
J
F
12:25
18:15
Southwest Airlines
WN 1301
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
12:55
18:45
Southwest Airlines
WN 3026
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:45
00:40
Southwest Airlines
WN 2395
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:55
00:50
Southwest Airlines
WN 2395
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
22:40
04:30
Southwest Airlines
WN 1511
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
22:40
04:30
Southwest Airlines
WN 2337
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
22:40
04:30
Southwest Airlines
WN 1565
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
Click to Check Prices
