Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
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 06/07/25 1 Stopover (MCO) NK2550, NK1309 27h 50min | Return 06/23/25 2 Stopovers (MCO, FLL) NK1310, NK2196, NK2188 35h 13min | | ![]() | $311 | ||
Best option Chicago San Jose, Costa Rica | Outbound 07/02/25 1 Stopover (GUA) AV0631, AV0653 18h 35min | Return 07/25/25 direct AV0630 07h 40min | | ![]() | ? | $370 found 3 days ago | |
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 found 3 days ago | ||
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 10/18/25 1 Stopover (FLL) NK0019, NK0335 07h 13min | Return 10/24/25 1 Stopover (GDL) Q64058, Y41704 17h 52min | | ![]() | $336 | ||
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 found 3 days ago | |
Chicago San Jose, Costa Rica | Outbound 10/18/25 1 Stopover (FLL) NK0019, NK0335 07h 13min | Return 10/24/25 1 Stopover (GDL) Q64058, Y41704 17h 52min | | ![]() | $350 |
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 | $ 301,53 |
---|---|
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 Washington DC - San Jose, Costa Rica from $ 242
- Flight Chicago O'Hare - San Jose, Costa Rica from $ 302
- Flight Orlando - San Jose, Costa Rica from $ 241
- Flight Tampa - San Jose, Costa Rica from $ 282
- Flight Dallas - San Jose, Costa Rica from $ 299
- Flight Atlanta - San Jose, Costa Rica from $ 274
- Flight Philadelphia - San Jose, Costa Rica from $ 356
Flight destinations with a similar price
- Flight Chicago - Jacksonville, Florida from $ 306
- Flight Chicago - San Antonio from $ 304