Nonstop flights from San Diego to Chicago

Southwest Airlines flies this route 3 to 4 times a day.

SANSan Diego International

1,726 mi · 24 flights a week

MDWChicago Midway International

SANMDW

When they leave

San Diego time

6:20a10:40pFirst departure 6:20 AM, last 10:40 PM

Five in the morning, 6:20 AM to 11:10 AM, then two in the evening, 5:50 PM to 10:40 PM.

Every flight

Earliest first

6:20 AM→12:20 PMSouthwest AirlinesBoeing 737 MAX 8Sun
6:45 AM→12:45 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri, Sun
6:55 AM→12:55 PMSouthwest AirlinesBoeing 737 MAX 8Tue, Wed, Sat
11:05 AM→5:00 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri
11:10 AM→5:05 PMSouthwest AirlinesBoeing 737 MAX 8Tue, Wed, Sat
5:50 PM→11:45 PMSouthwest AirlinesBoeing 737-700Mon, Thu, Fri
10:40 PM→4:30 AM⁺¹Southwest AirlinesBoeing 737-700Daily

Schedules last checked Sep 20, 2026. Times are local.

Flying from San Diego to Chicago

Southwest Airlines is the only airline flying nonstop from San Diego to Chicago, 3 to 4 times a day on the Boeing 737 MAX 8 and Boeing 737-700.

Flights run every day of the week, 4 on Mondays, Thursdays and Fridays and 3 on the other days. The first arrival in Chicago is at 12:20 PM and the last at 4:30 AM the next day. The flight covers 1,726 miles.

Flying back, Chicago to San Diego has 24 nonstop flights a week. From San Diego, O'Hare (ORD) is the other Chicago area airport with nonstop flights, 88 a week.