Flights from Chicago to San Juan

Flight deals from Chicago to San Juan

Looking for a cheap last-minute deal or the best return flight from Chicago to San Juan? If you want to travel next month, return fares start from $241. Find the lowest prices on one-way and return tickets right here.

Flying from Chicago to San Juan

Arm yourself with these facts on the fly.
Cheapest flight found$241
Cheapest month to flyMay
Average flight time4 hrs, 45 mins
Cheapest airport to fly fromChicago O'Hare International
Most popular airlineAmerican Airlines

Frequently asked questions

We looked at all of the upcoming return flights from Chicago to San Juan we could find over the next 12 months. It looks like $242 is the best price. This is good, compared to the average San Juan ticket price of $241.
The cheapest month to fly from Chicago to San Juan is currently May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to San Juan on Tuesday, 26 May 2026.
Chicago O'Hare International Airport offers direct flights to San Juan.
If you're flying from Chicago, 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 and San Juan is 4 hours and 44 minutes.