Direct flights from Chicago to San Juan
All flights from MDW to SJU non-stop. There are direct flights from Chicago Midway International, Illinois, USA to Luis Munoz Marin International (SJU), Puerto Rico twice a week with Southwest Airlines. The flight distance is 2070 miles and the trip usually takes about 4 hours and 40 minutes.
Airlines with non-stop routes:

Southwest Airlines

Frontier Airlines
No flights anymore
Flight schedule from Chicago to San Juan 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 2025-04-22
Chicago to San Juan flight departures
Select a date to see all scheduled flight departures between MDW to SJU.
MDW - SJU information
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Distance2070 miles (3331 km)
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Flight time4 hours and 40 minutes
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Airlines
Southwest
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AlliancesOne WorldSky TeamStar Alliance
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ClassesEconomyBusinessFirst Class
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Southwest AircraftBoeing 737 Passenger
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Arrival TerminalTerminal B (Southwest)