Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Chicago San Juan (Puerto Rico) | Outbound 11/03/25 1 Stopover (MCO) F92792, F93506 15h 44min | Return 11/12/25 1 Stopover (MCO) F94725, F93043 22h 15min | | ![]() | ? | $225 | |
Best option Chicago San Juan (Puerto Rico) | Outbound 10/18/25 direct NK1530 04h 47min | Return 11/17/25 direct NK1531 04h 58min | | ![]() | $232 | ||
Chicago San Juan (Puerto Rico) | Outbound 10/18/25 direct NK1530 04h 47min | Return 11/17/25 1 Stopover (ATL) F92871, F93397 09h 39min | | ![]() | ? | $231 | |
Chicago San Juan (Puerto Rico) | Outbound 10/18/25 direct NK1530 04h 47min | Return 11/17/25 direct NK1531 04h 58min | | ![]() | $233 | ||
Chicago San Juan (Puerto Rico) | Outbound 10/18/25 direct NK1530 04h 47min | Return 11/17/25 1 Stopover (PHL) F91015, F92111 12h 41min | | ![]() | $236 | ||
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 11/17/25 1 Stopover (MCO) F91823, F93043 10h 58min | | ![]() | $243 | ||
Chicago San Juan (Puerto Rico) | Outbound 10/18/25 direct NK1530 04h 47min | Return 11/17/25 direct NK1531 04h 58min | | ![]() | $245 | ||
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 09/23/25 1 Stopover (BOS) B61012, B60861 16h 34min | Return 09/30/25 1 Stopover (BOS) B60562, B60311 13h 54min | | ![]() | ? | $257 |
Stops
- Direct flight
Airline
- American Airlines
- Spirit 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 | $224.44 |
---|---|
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 $160
- Flight Detroit - San Juan (Puerto Rico) from $382
- Flight Orlando - San Juan (Puerto Rico) from $184
- Flight Miami - San Juan (Puerto Rico) from $204
- Flight Atlanta - San Juan (Puerto Rico) from $177
Flight destinations with a similar price
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- Flight Chicago - Morelia from $245