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11/26/2026
Find Chicago to San Juan Flights - Compare Airfare & Flight Deals
Looking for Chicago to San Juan flights? Compare fares from the airlines that fly this route in one search, with nonstop and connecting options when available. Flights from Chicago to San Juan may use more than one airport at either end, so check the nearby airports on this page when you search {Origin Code} to San Juan. Choose a departure time and cabin that suit you, then try a few dates around your preferred day to find better Chicago to San Juan flight deals. Fares and availability may change at any time.
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Chicago to San Juan Flight Deals
CHI Chicago Thu, Nov 26
SJU San Juan
from $109
Book Now
CHI Chicago Tue, Nov 24
SJU San Juan
from $109
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CHI Chicago Sun, Dec 6
SJU San Juan
from $112
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CHI Chicago Thu, Dec 3
SJU San Juan
from $139
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CHI Chicago Thu, Dec 10
SJU San Juan
from $139
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CHI Chicago Wed, Dec 9
SJU San Juan
from $139
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CHI Chicago Tue, Dec 8
SJU San Juan
from $139
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CHI Chicago Wed, Dec 9
SJU San Juan
from $139
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CHI Chicago Wed, Dec 2
SJU San Juan
from $139
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CHI Chicago Fri, Dec 4
SJU San Juan
from $139
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Read moreCheap Flights from Chicago to San Juan
Book your flights from Chicago to San Juan and on airfares. Check out the Spanish heritage or take a stroll in its colonial neighborhoods, San Juan is one of the pleasant destinations to visit and explore. It is the capital and the most populous municipality in Puerto Rico. To reach San Juan from Chicago, you can choose amongst the top airline that includes US Airways and American Airlines. Your flight to San Juan from Chicago takes about seven hours thirty minutes to cover a distance of about 2051 miles excluding layover time. For passing time watching in-flight movie is the best bet.
