Favorite airline: United Airlines
The most popular airline for flights from Chicago to San Juan (Puerto Rico) is United Airlines.
United Airlines
11 %
American Airlines
7 %
Interjet
4 %
Stopover flights are the cheapest connection
Compared to direct flights, flights with a stopover on this route are on average 70 % cheaper.
non stop flight
1 stop
2 stops
04h 53min
06h 56min
13h 36min
$268
$158
$427
The favorite connection is non-stop
Flights from Chicago to San Juan (Puerto Rico) are most often booked as a direct flight.
Route
bookings
Direct flights
04h 53min, from $268
36 %
1 stopover Fort Lauderdale-Hollywood International Airport, FL
06h 56min, from $158
24 %
1 stopover Orlando International Airport, FL
06h 50min, from $187
11 %