Nonstop flights from Chicago to San Diego

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

MDWChicago Midway International

1,726 mi · 24 flights a week

SANSan Diego International

MDWSAN

When they leave

Chicago time

6:10a8:45pFirst departure 6:10 AM, last 8:45 PM

Three in the morning, 6:10 AM to 10:15 AM, then three in the afternoon, 2:05 PM to 3:05 PM, then two in the evening, 8:25 PM to 8:45 PM.

Every flight

Earliest first

6:10 AM→8:20 AMSouthwest AirlinesBoeing 737 MAX 8Sun
6:15 AM→8:20 AMSouthwest AirlinesBoeing 737-700Daily
10:15 AM→12:25 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri
2:05 PM→4:10 PMSouthwest AirlinesBoeing 737 MAX 8Sat
2:50 PM→4:55 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri
3:05 PM→5:10 PMSouthwest AirlinesBoeing 737 MAX 8Tue, Wed
8:25 PM→10:35 PMSouthwest AirlinesBoeing 737 MAX 8Sun
8:45 PM→10:55 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Tue, Wed, Thu, Fri, Sat

Schedules last checked Sep 19, 2026. Times are local.

Flying from Chicago to San Diego

Southwest Airlines is the only airline flying nonstop from Chicago to San Diego, 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 San Diego is at 8:20 AM and the last at 10:55 PM. The flight covers 1,726 miles.

Flying back, San Diego to Chicago has 24 nonstop flights a week. O'Hare (ORD) also has nonstop flights to San Diego, 88 a week.

Return flights

San Diego to ChicagoView

Every Chicago airport

All Chicago to San Diego flightsView

Find the cheapest day to fly from Chicago to San Diego.

Schedules as of Oct 9, 2026.