Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Best option Chicago San Juan (Puerto Rico) | Outbound 10/18/25 direct NK1530 04h 47min | Return 10/24/25 direct NK1531 04h 58min | | ![]() | $240 | ||
Chicago San Juan (Puerto Rico) | Outbound 10/18/25 direct NK1530 04h 47min | Return 10/24/25 direct NK1531 04h 58min | | ![]() | $243 | ||
Chicago San Juan (Puerto Rico) | Outbound 10/18/25 direct NK1530 04h 47min | Return 10/24/25 direct NK1531 04h 58min | | ![]() | $252 | ||
Chicago San Juan (Puerto Rico) | Outbound 10/18/25 direct NK1530 04h 47min | Return 10/24/25 direct NK1531 04h 58min | | ![]() | $255 | ||
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 06/07/25 1 Stopover (MCO) NK2189, NK1989 07h 19min | Return 06/23/25 direct NK2534 05h 16min | | ![]() | $269 | ||
Chicago San Juan (Puerto Rico) | Outbound 06/07/25 1 Stopover (MCO) NK2550, NK1989 16h 17min | Return 06/23/25 direct NK2534 05h 16min | | ![]() | $273 | ||
Chicago San Juan (Puerto Rico) | Outbound 06/07/25 1 Stopover (MCO) NK2189, NK1989 07h 19min | Return 06/23/25 1 Stopover (FLL) NK2222, NK0002 13h 26min | | ![]() | $274 | ||
Chicago San Juan (Puerto Rico) | Outbound 06/07/25 1 Stopover (MCO) F93044, F94726 08h 27min | Return 06/23/25 direct NK2534 05h 16min | | ![]() | ? | $282 | |
Chicago San Juan (Puerto Rico) | Outbound 10/18/25 direct NK1530 04h 47min | Return 10/24/25 1 Stopover (JFK) B60904, B60405 10h 24min | | ![]() | ? | $288 |
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 | $ 239,23 |
---|---|
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 Baltimore - San Juan (Puerto Rico) from $ 161
- Flight Boston - San Juan (Puerto Rico) from $ 187
- Flight Detroit - San Juan (Puerto Rico) from $ 382
- Flight Los Angeles - San Juan (Puerto Rico) from $ 303
- Flight Orlando - San Juan (Puerto Rico) from $ 249
- Flight Atlanta - San Juan (Puerto Rico) from $ 177
- Flight Cleveland - San Juan (Puerto Rico) from $ 211
Flight destinations with a similar price
- Flight Chicago - San Francisco from $ 218
- Flight Chicago - Phoenix - Sky Harbor from $ 220
- Flight Chicago - Mexico City from $ 250
- Flight Chicago - Jacksonville, Florida from $ 222
- Flight Chicago - Morelia from $ 245
- Flight Chicago - Guadalajara from $ 243