Direct flights from San Diego to Chicago
All flights from SAN to MDW non-stop. There are direct flights from San Diego International Airport (SAN), California, USA to Chicago Midway International (MDW), Illinois, USA with Southwest Airlines. 24 weekly departures are currently scheduled on this route. Departure times range from 06:15 to 22:40 depending on the schedule period. The flight distance is 1734 miles (2790 km). Flight time ranges from 3 hours and 45 minutes to 4 hours and 15 minutes.
San Diego
, USA
Flight schedule from San Diego to Chicago with Southwest Airlines
This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.
Flight
The timetable & schedule information was updated at 2026-08-17
San Diego to Chicago scheduled departures
Select a date to see every published non-stop departure between SAN and MDW.
SAN - MDW route facts
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Distance1734 miles (2790 km)
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Flight time3 hours and 45 minutes to 4 hours and 15 minutes
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Airline Southwest
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Airline alliancesLow-cost carrier
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CabinsEconomy
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Departure terminalsTerminal 1
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AircraftBoeing 737MAX 8 Passenger, Boeing 737-800 (winglets) Passenger/BBJ2 and Boeing 737-700 Passenger (Scimitar Winglets)
Route FAQ
Direct flights from San Diego to IL, USA
From San Diego to Chicago
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