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Cheap flights from San Juan to Chicago

Fares from $105 in January 2027. Compare every month below, then book with the site you like.

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Cheapest San Juan to Chicago fares by month

Lowest price per person found in recent searches. Prices change often and are checked when you book.

San Juan to Chicago at a glance

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Frequently asked questions

How much is a flight from San Juan to Chicago?
The cheapest fare we found recently is $105 per person, departing Jan 12 on Frontier. Prices change daily, so search your dates to see today's fares.
What is the cheapest month to fly from San Juan to Chicago?
January 2027 is currently the cheapest month, from $105. December 2026 is the most expensive, from $142.
Are there direct flights from San Juan to Chicago?
The cheapest fares we found recently have at least one stop. Nonstop flights may still exist at a higher price; tick "Direct only" in the search to check.
Which airlines fly from San Juan to Chicago?
The cheapest recent fares on this route were on Frontier, JetBlue.
How long is the flight from San Juan to Chicago?
San Juan and Chicago are about 2,074 miles apart, so a nonstop flight takes roughly 5h. Flights with a stop take longer, depending on the connection.
How do I find the cheapest flight from San Juan to Chicago?
Search your dates on Gotoesy. We list fares from several booking sites sorted cheapest first, show nearby dates when your day has no saved fare, and send you straight to the seller to book.

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