Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Chicago San Jose, Costa Rica | Outbound 11/09/25 1 Stopover (MCO) NK1880, Q64001 28h 58min | Return 12/07/25 1 Stopover (MCO) Q64000, NK2530 13h 53min | | ![]() | $302 | ||
Best option Chicago San Jose, Costa Rica | Outbound 11/09/25 direct AA0353 05h 00min | Return 12/07/25 direct AA0326 05h 31min | | ![]() | ? | $402 | |
Chicago San Jose, Costa Rica | Outbound 11/09/25 1 Stopover (FLL) NK0002, NK0335 07h 09min | Return 12/07/25 1 Stopover (FLL) NK1756, NK1986 08h 07min | | ![]() | $330 | ||
Chicago San Jose, Costa Rica | Outbound 11/09/25 1 Stopover (PTY) CM0229, CM0344 18h 58min | Return 12/07/25 1 Stopover (FLL) NK0338, NK0001 10h 23min | | ![]() | ? | $347 | |
Chicago San Jose, Costa Rica | Outbound 11/09/25 1 Stopover (PTY) CM0229, CM0818 18h 12min | Return 12/07/25 1 Stopover (ATL) DL1756, DL1199 09h 30min | | ![]() | ? | $367 | |
Chicago San Jose, Costa Rica | Outbound 02/13/26 1 Stopover (GDL) Y41705, Q64059 10h 57min | Return 02/26/26 1 Stopover (MCO) Q64000, NK2530 13h 53min | | ![]() | $386 | ||
Chicago San Jose, Costa Rica | Outbound 11/09/25 1 Stopover (PTY) CM0229, CM0344 18h 58min | Return 12/07/25 direct AA0326 05h 31min | | ![]() | ? | $476 | |
Chicago San Jose, Costa Rica | Outbound 02/13/26 1 Stopover (GDL) Y41705, Q64059 10h 57min | Return 02/26/26 1 Stopover (MEX) Q64050, Y40700 13h 53min | | ![]() | ? | $476 | |
Chicago San Jose, Costa Rica | Outbound 02/13/26 1 Stopover (FLL) NK0002, NK0335 07h 09min | Return 02/26/26 2 Stopovers (JFK, BOS) B61794, B60118, B60311 20h 24min | | ![]() | ? | $489 | |
Chicago San Jose, Costa Rica | Outbound 02/13/26 1 Stopover (FLL) NK0002, NK0335 07h 09min | Return 02/26/26 1 Stopover (FLL) NK0338, NK3153 07h 41min | | ![]() | $492 |
Stops
- Direct flight
Airline
- Copa Airlines
- Spirit Airlines
- Volaris
- United Airlines
- Sun Country Airlines
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 | 301,13 $ |
---|---|
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 (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 324 $
- Flight Washington DC - San Jose, Costa Rica from 274 $
- Flight Chicago O'Hare - San Jose, Costa Rica from 302 $
- Flight San Francisco - San Jose, Costa Rica from 629 $
- Flight Dallas - San Jose, Costa Rica from 320 $
- Flight Newark - San Jose, Costa Rica from 445 $
- Flight Atlanta - San Jose, Costa Rica from 239 $
- Flight New York - San Jose, Costa Rica from 362 $
- Flight New York - San Jose, Costa Rica from 362 $
- Flight Baltimore - San Jose, Costa Rica from 273 $
Flight destinations with a similar price
- Flight San Jose, Costa Rica - Havana from 366 $
- Flight San Jose, Costa Rica - Mexico City from 321 $
- Flight San Jose, Costa Rica - Santo Domingo from 188 $
- Flight San Jose, Costa Rica - Zurich from 1.182 $
- Flight San Jose, Costa Rica - Cancun from 233 $
Flight destinations with a similar price
- Flight Chicago - Mexico City from 286 $
- Flight Chicago - Morelia from 296 $
- Flight Chicago - Toronto from 283 $