Direct flights from Chicago Midway to San Juan INTL
2 nonstop flights a week on 1 airline. Zero layovers — one hop from MDW to SJU.
Flight time: about 4h16m nonstop
Which days does it fly?
When does it fly?
Departure times in Chicago Midway local time, from flights observed over the last 7 days.
| Flight | Departs | Duration | Days |
|---|---|---|---|
| Southwest SWA1924 | 8:04a | 4h21m | Sat |
| Southwest SWA2531 | 9:29a | 4h10m | Sun |
Southwest
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The route
One hop: MDW → SJUDrag to pan · scroll with ⌘/Ctrl to zoom · arrow keys when focused
Nonstop from Chicago Midway (MDW) to San Juan (SJU)
Chicago Midway International Airport (MDW) has 2 nonstop flights a week to San Juan (SJU), operated by Southwest. No layovers, no connections — one hop out of MDW and you're there.
This route flies on Saturday and Sunday — check the schedule grid above before you pick a travel day. San Juan is an international destination — don't forget your passport. Route data updated July 2026 from observed departures.
Route data updated July 2026 from observed flight departures. Schedules change — always confirm with the airline before booking.
How long is the flight from Chicago Midway to San Juan?
The nonstop flight from Chicago Midway (MDW) to San Juan (SJU) takes about 4h16m in the air, based on recently observed nonstop departures.
How long does it take to drive from Chicago Midway to San Juan?
There's no driving from Chicago Midway to San Juan — there's an ocean in the way, so flying is the only way to do it. Bunnies don't like to swim. 🐇