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Direct flights from Chicago to San Juan

Airlines Schedules

MDW - SJU route map All flights from MDW to SJU non-stop. There are direct flights from Chicago Midway International (MDW), Illinois, USA to Luis Munoz Marin International (SJU), Puerto Rico with Southwest Airlines. 2 weekly departures are currently scheduled on this route. Departure times range from 07:45 to 08:55 depending on the schedule period. The flight distance is 2070 miles (3331 km). Flight time ranges from 4 hours and 35 minutes to 4 hours and 50 minutes.

MDW
Chicago Midway
USAChicago , USA
SJU
Luis Munoz Marin
Puerto RicoSan Juan , Puerto Rico
MDW
Chicago Midway
USAChicago , USA
Luis Munoz Marin
Puerto RicoSan Juan , Puerto Rico
SJU
Flight time 4h 35min to 4h 50min
Updated Jul 12, 2026
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Airlines with non-stop routes:

Southwest Airlines Low-cost carrier

Departure times vary between 07:45 and 08:55
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2 flights/week
2 flights/week
Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS
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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.

 
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The timetable & schedule information was updated at

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Chicago to San Juan scheduled departures

Select a date to see every published non-stop departure between MDW and SJU.

Thursday
Thu
Aug 06
0 flights(0)
Friday
Fri
Aug 07
0 flights(0)
Saturday
Sat
Aug 08
0 flights(0)
Sunday
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Aug 09
0 flights(0)
Monday
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Aug 10
0 flights(0)
Tuesday
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Aug 11
0 flights(0)
Wednesday
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Aug 12
0 flights(0)
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MDW-SJU flight route
Route map from Chicago, MDW to San Juan, SJU. The distance is 2070 miles or 3331 km.
Chicago - San Juan direct flight map
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MDW - SJU route facts

  • Distance
    2070 miles (3331 km)
  • Flight time
    4 hours and 35 minutes to 4 hours and 50 minutes
  • Airline
    Southwest Southwest
  • Airline alliances
    Low-cost carrier
  • Cabins
    Economy
  • Arrival terminals
    Terminal B
  • Aircraft
    Boeing 737MAX 8 Passenger and Boeing 737-700 Passenger (Scimitar Winglets)

Route FAQ

Southwest Airlines operates non-stop flights from MDW to SJU with 2 weekly departures.

Scheduled flight time from MDW to SJU ranges from 4 hours and 35 minutes to 4 hours and 50 minutes. The route covers 2070 miles (3331 km).

2 weekly departures are currently scheduled on this route, with published departure times ranging from 07:45 to 08:55 depending on the schedule period.

Arrival terminal: Terminal B.

Economy are currently scheduled on non-stop flights for this route.
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