Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Chicago San Juan (Puerto Rico) | Outbound 04/21/25 2 Stopovers (ATL, MCO) F91596, F94556, F94726 39h 29min | Return 05/19/25 2 Stopovers (BWI, ATL) F92265, F92509, F91595 35h 43min | | ![]() | ? | $197 | |
Best option Chicago San Juan (Puerto Rico) | Outbound 09/19/25 direct NK1530 04h 47min | Return 09/29/25 direct NK1531 04h 58min | | ![]() | $258 | ||
Chicago San Juan (Puerto Rico) | Outbound 04/29/25 1 Stopover (MIA) NK0492, NK0218 12h 26min | Return 05/08/25 1 Stopover (ATL) NK2405, NK2707 21h 19min | | ![]() | $204 | ||
Chicago San Juan (Puerto Rico) | Outbound 04/29/25 1 Stopover (MIA) NK0492, NK0218 12h 26min | Return 05/08/25 1 Stopover (IAH) NK2528, NK2174 11h 49min | | ![]() | $211 | ||
Chicago San Juan (Puerto Rico) | Outbound 04/29/25 1 Stopover (MIA) NK0492, NK0218 12h 26min | Return 05/08/25 1 Stopover (ATL) NK2405, NK2707 21h 19min | | ![]() | $213 | ||
Chicago San Juan (Puerto Rico) | Outbound 04/29/25 1 Stopover (MIA) NK0492, NK0218 12h 26min | Return 05/08/25 1 Stopover (IAH) NK2528, NK2174 11h 49min | | ![]() | ? | $215 | |
Chicago San Juan (Puerto Rico) | Outbound 04/29/25 1 Stopover (MIA) NK0492, NK0218 12h 26min | Return 05/08/25 1 Stopover (IAH) NK2528, NK2174 11h 49min | | ![]() | ? | $218 | |
Chicago San Juan (Puerto Rico) | Outbound 04/29/25 1 Stopover (MIA) NK0492, NK0218 12h 26min | Return 05/08/25 1 Stopover (IAH) NK2528, NK2174 11h 49min | | ![]() | $219 | ||
Chicago San Juan (Puerto Rico) | Outbound 04/29/25 1 Stopover (MIA) NK0492, NK0218 12h 26min | Return 05/08/25 1 Stopover (MCO) F94725, F92791 07h 53min | | ![]() | ? | $243 | |
Chicago San Juan (Puerto Rico) | Outbound 09/19/25 direct NK1530 04h 47min | Return 09/29/25 direct NK1531 04h 58min | | ![]() | $261 |
Stops
- Direct flight
Airline
- Spirit Airlines
- American Airlines
- United Airlines
- Frontier Airlines
- JetBlue Airways
Tips and tricks to help you find cheap flights from Chicago to San Juan (Puerto Rico)
Favorite airline: American Airlines
79 % of flights booked on the route from Chicago to San Juan (Puerto Rico) are booked with American Airlines, Spirit Airlines and United Airlines.

American Airlines
29 %

Spirit Airlines
27 %

United Airlines
23 %
Direct flights are the cheapest connection
On this route, direct flights are $ 2.00 cheaper than flights with a stopover.
non stop flight
1 stop
2 stops
04h 39min
13h 20min
15h 45min
$194
$196
$451
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 39min, from $194
39 %
1 stopover Orlando International Airport, FL
07h 00min, from $221
18 %
1 stopover Charlotte Douglas International Airport, NC
13h 01min, from $338
15 %
Important flight information
Flight information: Chicago - San Juan (Puerto Rico)
Roundtrip from | $196.13 |
---|---|
Flight duration | min. 04:30 / max. 07:00 |
Return flight duration | min. 05:10/ max. 06:05 |
Distance | 3318 km |
Flights per week | 28 |
Departure airport | Airport Chicago-IL all Airports (ORD, MDW, RFD) (CHI) |
Arrival airport | Airport San Juan - Luis Muñoz Marín International Airport (SJU) |
Destination country | Flights to Puerto Rico |
Alternative flights to San Juan (Puerto Rico)
- Flight Boston - San Juan (Puerto Rico) from $187
- Flight Detroit - San Juan (Puerto Rico) from $177
- Flight Orlando - San Juan (Puerto Rico) from $284
- Flight Miami - San Juan (Puerto Rico) from $230
- Flight Atlanta - San Juan (Puerto Rico) from $115
Flight destinations with a similar price
- Flight Chicago - Seattle-Tacoma from $198
- Flight Chicago - Louisville from $207
- Flight Chicago - Toronto from $203