Flights from San Juan Airport (MDW) to San Juan

Flight deals from Chicago Midway Airport to San Juan

Looking for cheap tickets from Chicago Midway Airport to San Juan, or a last-minute trip? Find the lowest prices on one-way and return tickets right here.

Flying from Chicago Midway Airport to San Juan

Arm yourself with these facts on the fly.
Cheapest flight foundC$121
Cheapest month to flyFebruary
Average flight time4 hrs, 39 mins
Average flights per week2
Most popular airlineSouthwest Airlines

Frequently asked questions

Chicago O'Hare International Airport offers direct flights to San Juan.
We looked at all of the upcoming return flights from Chicago Midway Airport to San Juan we could find over the next 12 months. It looks like C$247 is the best price. This is good, compared to the average San Juan ticket price of C$247.
The cheapest month to fly from Chicago Midway Airport to San Juan is currently February.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago Midway Airport to San Juan on Saturday, February 21, 2026.
If you're flying from Chicago Midway, the cheapest city in San Juan to fly into is San Juan. The cheapest airport serving San Juan at the moment is San Juan Luis Munoz Marin.
The average flight time between Chicago Midway Airport and San Juan is 4 hours and 39 minutes.