Flight Routes from Chicago to San Jose, Costa Rica

Trip type

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
Best option
Chicago
San Jose, Costa Rica
Outbound
05/16/26
1 Stopover (FLL)
NK1986, NK0335
07h 07min
Return
05/29/26
1 Stopover (FLL)
NK0338, NK0001
10h 10min
Spirit Airlines
$357
Chicago
San Jose, Costa Rica
Please note: transfer for connecting flight
Outbound
05/16/26
2 Stopovers (LGA, JFK, SAL)
NK0932, AV0567, AV0319
24h 41min
Return
05/29/26
1 Stopover (FLL)
NK0338, NK0581
30h 17min
Spirit Airlines, Avianca
$361
Chicago
San Jose, Costa Rica
Outbound
05/16/26
1 Stopover (MEX)
AM0689, AM0690
11h 05min
Return
05/29/26
1 Stopover (MEX)
AM0657, AM0682
15h 45min
Aeroméxico
$876
Chicago
San Jose, Costa Rica
Outbound
05/16/26
1 Stopover (PTY)
CM0229, CM0787
16h 51min
Return
05/29/26
1 Stopover (PTY)
CM0341, CM0235
14h 10min
Copa Airlines ?
$486
Chicago
San Jose, Costa Rica
Outbound
05/16/26
1 Stopover (PTY)
CM0229, CM0787
16h 51min
Return
05/29/26
1 Stopover (PTY)
CM0193, CM0235
13h 13min
Copa Airlines ?
$506
Chicago
San Jose, Costa Rica
Outbound
05/16/26
1 Stopover (JFK)
B61306, B61793
29h 29min
Return
05/29/26
1 Stopover (FLL)
NK0338, NK0001
10h 10min
JetBlue Airways ?
$510
Chicago
San Jose, Costa Rica
Outbound
07/26/26
1 Stopover (MCO)
F93044, Y44001
23h 04min
Return
08/05/26
1 Stopover (MCO)
Y44000, F92791
15h 41min
Frontier Airlines, Volaris ?
$511
Chicago
San Jose, Costa Rica
Outbound
05/16/26
1 Stopover (MIA)
F92672, AA1593
20h 15min
Return
05/29/26
2 Stopovers (GUA, MEX)
CM0391, Y44063, Y40700
32h 57min
Frontier Airlines, American Airlines ?
$523
Chicago
San Jose, Costa Rica
Outbound
07/26/26
1 Stopover (FLL)
NK1986, NK0335
07h 12min
Return
08/05/26
1 Stopover (FLL)
NK0338, NK0001
10h 01min
Spirit Airlines
$544
Chicago
San Jose, Costa Rica
Outbound
07/26/26
1 Stopover (FLL)
NK1986, NK0335
07h 12min
Return
08/05/26
1 Stopover (FLL)
NK0338, NK0001
10h 01min
Spirit Airlines
$552
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 $ 356,84
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