There are most likely no direct flights on the San Juan — Chicago route
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The cost of a one-way flight from San Juan to Chicago ranges from $101 (October 2026) to $123 (January 2027). On average, the ticket price is about $112–$123.
A non-stop flight is the most convenient and comfortable way to fly from San Juan to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
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Answers to questions about the route that travelers are most interested in.
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There are most likely no direct flights on the San Juan — Chicago route
All airports
San Juan — Chicago
11/08/2026
Departure
Direct flight
AA2279
starting at $528
San Juan — Chicago
12/23/2026
Departure
Direct flight
UA2089
starting at $217
San Juan — Chicago
10/27/2026
Departure
Direct flight
UA2088
starting at $247
Flights from San Juan to Chicago are operated by several airlines — American Airlines, United Airlines, and Frontier Airlines. This allows passengers to flexibly choose flights based on departure time, cost, and additional services. The minimum ticket price starts at $126, making this destination accessible to travelers with different budgets. We help compare all available options in real time, so you can book tickets at the best value for money. The service ensures transparent search and lets you book affordable flights in just a few clicks.
The cheapest flight ticket from San Juan to Chicago according to data for the last 48 hours costs $126
Often the best time to buy tickets from San Juan to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from San Juan to Chicago can be found flying in these months: October, January.
The fastest flights from San Juan to Chicago start from 8 hours 48 minutes in the air.
The following airlines operate direct flights on the route San Juan — Chicago: American Airlines, United Airlines
The cheapest one-way flight from San Juan to Chicago departs on 10/27/2026, is operated by Frontier Airlines and costs $126
There is no information about the cheapest roundtrip flight from San Juan to Chicago
Fastest flight from San Juan to Chicago takes 8h 48m
There are direct flights on this route 3 days a week: Su, Tu, and We
The distance between San Juan and Chicago is 3305km (2049 miles). There are 27 direct flights from San Juan to Chicago. The time difference between San Juan and Chicago is 2h. Flights from San Juan begin at 7:40 AM. The latest flight from San Juan departs at 12:55 AM
We couldn't find any special offers for flights from San Juan to Chicago