Direct flights from San Diego to Chicago SAN → MDW
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). Arrivals run on time 75.8% at SAN and 72.8% at MDW — BTS data for the last three months, counting arrivals within 15 minutes of schedule. Schedule data from 30 July 2026.
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Southwest Airlines
WN
Departure Schedule typical week
Typical weekly schedule · 21 flights per week (~3 per day) · Updated 31d ago
Southwest Airlines
Frequently asked questions
Is there a direct flight from San Diego to Chicago?
Yes, Southwest Airlines operates nonstop flights from San Diego (SAN) to Chicago (MDW).
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 multiple daily — 21 flights per week (~3 per day).
What is the on-time performance for flights from San Diego to Chicago?
Arrivals run on time 75.8% at SAN and 72.8% at MDW — BTS data for the last three months, counting arrivals within 15 minutes of schedule.
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.
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