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Direct flights from San Juan to Chicago

Airlines Schedules

SJU - MDW route map All flights from SJU to MDW non-stop. There are direct flights from Luis Munoz Marin International (SJU), Puerto Rico to Chicago Midway International (MDW), Illinois, USA with Southwest Airlines. 2 weekly departures are currently scheduled on this route. Departure times range from 05:30 to 16:30 depending on the schedule period. The flight distance is 2070 miles (3331 km). Flight time ranges from 4 hours and 50 minutes to 5 hours and 5 minutes.

SJU
Luis Munoz Marin
Puerto RicoSan Juan , Puerto Rico
MDW
Chicago Midway
USAChicago , USA
SJU
Luis Munoz Marin
Puerto RicoSan Juan , Puerto Rico
Chicago Midway
USAChicago , USA
MDW
Flight time 4h 50min to 5h 5min
Updated Jun 29, 2026
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Airlines with non-stop routes:

Southwest Airlines Low-cost carrier

Departure times vary between 05:30 and 16:30 • From Terminal B
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2 flights/week
2 flights/week
Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS
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Flight schedule from San Juan 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.

 
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The timetable & schedule information was updated at

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San Juan to Chicago scheduled departures

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

Thursday
Thu
Aug 06
0 flights(0)
Friday
Fri
Aug 07
0 flights(0)
Saturday
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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)
Time
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SJU-MDW flight route
Route map from San Juan, SJU to Chicago, MDW. The distance is 2070 miles or 3331 km.
San Juan - Chicago direct flight map
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SJU - MDW route facts

  • Distance
    2070 miles (3331 km)
  • Flight time
    4 hours and 50 minutes to 5 hours and 5 minutes
  • Airline
    Southwest Southwest
  • Airline alliances
    Low-cost carrier
  • Cabins
    Economy
  • Departure terminals
    Terminal B
  • Aircraft
    Boeing 737MAX 8 Passenger and Boeing 737-800 (winglets) Passenger/BBJ2

Route FAQ

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

Scheduled flight time from SJU to MDW ranges from 4 hours and 50 minutes to 5 hours and 5 minutes. The route covers 2070 miles (3331 km).

2 weekly departures are currently scheduled on this route, with published departure times ranging from 05:30 to 16:30 depending on the schedule period.

Departure terminal: Terminal B.

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