Direct flights from San Diego to Chicago
- ~3 flights a day
- Southwest Airlines
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When the nonstops leave
Typical weekly schedule · 21 flights per week (~3 per day) · Updated 81d ago
Arrive the same day
6:30 AM
8:20 AMSat
10:45 AMSat
Arrive the same day
12:10 PM5 days a week
5:30 PM4 days a week
Arrive the next morning
10:40 PMMon, Thu, Fri
Southwest Airlines
Departs Terminal 1
Frequently asked questions
Is there a direct flight from San Diego to Chicago?
Yes. Southwest Airlines flies nonstop from San Diego (SAN) to Chicago (MDW), several times daily. The flight takes about 4h 4m and covers 1,725 miles (2,776 km). Schedule data from 30 July 2026.
Which airlines fly direct from San Diego to Chicago?
Southwest Airlines operates nonstop flights from San Diego to Chicago.
How long is the flight from San Diego to Chicago?
The nonstop flight from San Diego to Chicago takes ~4h 4m (approximately 2776 km).
How often do direct flights operate from San Diego to Chicago?
Nonstop flights from San Diego to Chicago operate several times daily — 21 flights per week (~3 per day).
What days of the week are there direct flights from San Diego to Chicago?
Direct flights from San Diego to Chicago operate every day of the week.