Flights from Chicago to San Jose, Costa Rica

Our cheapest offers for flights from Chicago to San Jose, Costa Rica

Here you can compare cheap flights from Chicago (CHI) to San Jose, Costa Rica (SJO) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to San Jose, Costa Rica. Prices and availability may change at any time.

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
Spirit Airlines
$294
Best option
Chicago
San Jose, Costa Rica
Outbound
11/03/25
direct
AA0353
05h 12min
Return
11/12/25
direct
AA0314
05h 38min
American Airlines ?
$610
Chicago
San Jose, Costa Rica
Pay attention to transfer at connecting flight
Outbound
10/18/25
1 Stopover (MCO)
NK0507, Q64001
20h 34min
Return
11/17/25
1 Stopover (MCO)
NK1310, NK1109
29h 17min
Spirit Airlines, Volaris Costa Rica
$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
Aeroméxico
$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
Spirit Airlines
$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
Spirit Airlines
$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
Spirit Airlines
$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
Frontier Airlines
$305
Chicago
San Jose, Costa Rica
Outbound
07/08/25
1 Stopover (MCO)
NK2191, NK1309
15h 40min
Return
08/07/25
1 Stopover (GUA)
AV0654, AV0630
21h 05min
Spirit Airlines ?
$311
Chicago
San Jose, Costa Rica
Outbound
07/08/25
1 Stopover (MCO)
NK2191, NK1309
15h 40min
Return
08/07/25
1 Stopover (GUA)
AV0654, AV0630
21h 05min
Spirit Airlines ?
$313
Prices based on recent searches, subject to last-minute changes
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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 destinations with a similar price
Flight destinations with a similar price