Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Chicago San Jose, Costa Rica | Outbound 09/23/25 1 Stopover (MCO) NK0507, NK1309 18h 01min | Return 09/30/25 1 Stopover (MEX) Q64050, Y40700 13h 54min | | ![]() | $294 | ||
Best option Chicago San Jose, Costa Rica | Outbound 11/03/25 direct AA0353 05h 12min | Return 11/12/25 direct AA0314 05h 38min | | ![]() | ? | $610 | |
Chicago San Jose, Costa Rica | Outbound 06/07/25 1 Stopover (MCO) NK2550, NK1309 27h 50min | Return 06/23/25 2 Stopovers (MCO, FLL) NK1310, NK2196, NK2188 35h 13min | | ![]() | $311 | ||
Chicago San Jose, Costa Rica | Outbound 07/02/25 1 Stopover (MEX) AM0689, AM0690 11h 11min | Return 07/25/25 1 Stopover (MEX) AM0691, AM0682 09h 46min | | ![]() | $850 | ||
Chicago San Jose, Costa Rica | Outbound 09/23/25 1 Stopover (MCO) NK0507, NK1309 18h 01min | Return 09/30/25 1 Stopover (MCO) NK1310, NK1109 29h 17min | | ![]() | $296 | ||
Chicago San Jose, Costa Rica | Outbound 09/19/25 2 Stopovers (IAH, FLL) NK1339, NK0221, NK0335 19h 48min | Return 09/29/25 1 Stopover (GDL) Q64058, Y41704 17h 52min | | ![]() | $302 | ||
Chicago San Jose, Costa Rica | Outbound 09/19/25 2 Stopovers (IAH, FLL) NK1339, NK0221, NK0335 19h 48min | Return 09/29/25 1 Stopover (GDL) Q64058, Y41704 17h 52min | | ![]() | $304 | ||
Chicago San Jose, Costa Rica | Outbound 06/08/25 1 Stopover (MEX) Y40701, Q64051 13h 17min | Return 06/12/25 1 Stopover (MEX) Q64050, Y40700 13h 54min | | ![]() | $310 | ||
Chicago San Jose, Costa Rica | Outbound 09/19/25 1 Stopover (GDL) Y41705, Q64059 12h 07min | Return 09/29/25 1 Stopover (GDL) Q64058, Y41704 17h 52min | | ![]() | ? | $335 | |
Chicago San Jose, Costa Rica | Outbound 07/02/25 2 Stopovers (GUA, SAL) AV0631, AV0579, AV0639 17h 55min | Return 07/25/25 2 Stopovers (GUA, SAL) AV0652, AV0579, AV0408 22h 15min | | ![]() | ? | $346 |
Stops
- Direct flight
Airline
- American Airlines
- Spirit Airlines
- Avianca
- United Airlines
- Volaris
Tips and tricks to help you find cheap flights from Chicago to San Jose, Costa Rica
Favorite airline: Copa
Flight tickets on the route Chicago – San Jose, Costa Rica are most frequently booked with Copa.

Copa
26 %

Spirit Airlines
23 %

United Airlines
19 %
Direct flights are more expensive
On this route, direct flights are $173.00 more expensive than flights with a stopover.
non stop flight
1 stop
2 stops
06h 45min
25h 29min
15h 50min
$452
$279
$352
Favourite connection: via Panama City
35 % of booked tickets on this route are for flights with a transfer in Panama City.
Route
bookings
1 stopover Panama City-Tocumen International
30h 15min, from $412
35 %
1 stopover Houston - George Bush Intercontinental Airport, TX
13h 56min, from $311
23 %
1 stopover Mexico City-Juarez International
17h 13min, from $634
12 %
Important flight information
Flight information: Chicago - San Jose, Costa Rica
Roundtrip from | $293.39 |
---|---|
Flight duration | min. 05:12 |
Return flight duration | min. 05:37 |
Distance | 3566 km |
Flights per week | 8 |
Departure airport | Airport Chicago-IL all Airports (ORD, MDW, RFD) (CHI) |
Arrival airport | Airport San Jose, Costa Rica (SJO) |
Destination country | Flights to Costa Rica |
Alternative flights to San Jose, Costa Rica
- Flight Boston - San Jose, Costa Rica from $275
- Flight Miami - San Jose, Costa Rica from $204
- Flight Orlando - San Jose, Costa Rica from $222
- Flight Tampa - San Jose, Costa Rica from $282
- Flight Dallas - San Jose, Costa Rica from $299
Flight destinations with a similar price
- Flight Chicago - Montego Bay from $317
- Flight Chicago - Cancun from $266