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 10/18/25 1 Stopover (MCO) NK0507, Q64001 20h 34min | Return 11/17/25 1 Stopover (MCO) NK1310, NK1109 29h 17min | | ![]() | $347 | ||
Chicago San Jose, Costa Rica | Outbound 09/19/25 1 Stopover (MEX) AM0683, AM0690 10h 53min | Return 09/29/25 1 Stopover (MEX) AM0657, AM0682 15h 43min | | ![]() | $867 | ||
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 10/10/25 1 Stopover (ATL) F93398, F90215 27h 18min | Return 11/04/25 1 Stopover (MEX) Q64050, Y40700 13h 54min | | ![]() | $305 | ||
Chicago San Jose, Costa Rica | Outbound 10/10/25 1 Stopover (ATL) F93398, F90215 27h 18min | Return 11/04/25 1 Stopover (MEX) Q64050, Y40700 13h 54min | | ![]() | $319 | ||
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 |
Stops
- Direct flight
Airline
- American Airlines
- United Airlines
- Spirit Airlines
- Volaris
- Frontier 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 | 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 (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 318 $
- Flight Washington DC - San Jose, Costa Rica from 200 $
- Flight Los Angeles - San Jose, Costa Rica from 230 $
- Flight Miami - San Jose, Costa Rica from 204 $
- Flight Chicago O'Hare - San Jose, Costa Rica from 294 $
- Flight San Francisco - San Jose, Costa Rica from 375 $
- Flight Orlando - San Jose, Costa Rica from 222 $
- Flight Tampa - San Jose, Costa Rica from 282 $
- Flight Dallas - San Jose, Costa Rica from 302 $
Flight destinations with a similar price
- Flight San Jose, Costa Rica - Zurich from 452 $
Flight destinations with a similar price
- Flight Chicago - Montego Bay from 317 $
- Flight Chicago - Cancun from 269 $
- Flight Chicago - Morelia from 284 $