Looking for more low-fare flights?
Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.
Find low faresSouthwest® flights from San Juan to Chicago (Midway)
expand_more
1 Passenger
expand_morePromo Code
expand_moretoday
today
Low fares from San Juan to Chicago (Midway)
$
There are no fares that match your filter criteria. Please adjust your filters.
There are no fares that match your filter criteria. Please adjust your filters.Explore flights from San Juan to Chicago (Midway)
location_on
location_on
Flight Details
Departing from:
Luis Muñoz Marín International Airport
Arriving at:
Chicago Midway International Airport
Distance:
2057 miles
Route Information
101† Weekly flights
† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.
‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.
Questions we hear the most
There are 101 weekly flights from San Juan to Chicago (Midway) on Southwest Airlines.
To find the lowest fares by day and time to fly San Juan to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
You can rent a car at Chicago Midway International Airport book yours with your flight.
Yes! Flights from San Juan to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.