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Tips and tricks to help you find cheap flights from Chicago to San Juan (Puerto Rico)

Favorite airline: United Airlines
Most travelers looking for flights on the route from Chicago to San Juan (Puerto Rico) decide to book flights with United Airlines.
United Airlines
9 %
American Airlines
8 %
4 %
Stopover flights are the cheapest connection
Direct flights on this route are $110.00 more expensive on average than flights with a stopover.
non stop flight
1 stop
2 stops
04h 53min
06h 56min
13h 25min
The favorite connection is non-stop
Non-stop flights are especially popular on this route. 31 % of travelers will book a direct flight.
Direct flights
04h 53min, from $268
31 %
1 stopover Fort Lauderdale-Hollywood International Airport, FL
06h 56min, from $158
22 %
1 stopover Orlando International Airport, FL
06h 50min, from $187
13 %
Flight information Chicago - San Juan (Puerto Rico)
Cheap direct flights
Flight details Chicago - San Juan (Puerto Rico)
  • Flight duration: min. 04:30 / max. 07:00
  • Distance: 3318 km
  • Flights per week: 28
  • Return flight duration: min. 05:10 / max. 06:05