Flights from Chicago to San Jose, Costa Rica

  • Find cheap flights
  • Booking tips

Book cheap flights fast with idealo

Save time & money: find cheap flights fast
Easy to use: filter & sort to find the best flight
Free to use: compare offers & book flights

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
02/19/25
1 Stopover (FLL)
NK1986, NK1755
16h 29min
Return
03/10/25
1 Stopover (MEX)
Q64050, Y40700
13h 45min
Spirit Airlines
$308
Best option
Chicago
San Jose, Costa Rica
Outbound
02/19/25
1 Stopover (FLL)
NK0001, NK1755
08h 39min
Return
03/10/25
1 Stopover (BOG)
AV0693, AV0262
10h 00min
Spirit Airlines ?
$379
Chicago
San Jose, Costa Rica
Outbound
02/19/25
1 Stopover (FLL)
NK1986, NK1755
16h 29min
Return
03/10/25
1 Stopover (MEX)
Q64050, Y40700
13h 45min
Spirit Airlines
$317
Chicago
San Jose, Costa Rica
Outbound
03/02/25
1 Stopover (MEX)
Y40701, Q64051
13h 09min
Return
03/07/25
1 Stopover (MEX)
Q64050, Y40700
13h 45min
Volaris, Volaris Costa Rica
$345
Chicago
San Jose, Costa Rica
Outbound
03/02/25
1 Stopover (MEX)
Y40701, Q64051
13h 09min
Return
03/07/25
1 Stopover (MEX)
Q64050, Y40700
13h 45min
Volaris, Volaris Costa Rica
$351
Chicago
San Jose, Costa Rica
Outbound
03/02/25
1 Stopover (MEX)
Y40701, Y44051
13h 09min
Return
03/07/25
1 Stopover (MEX)
Y44050, Y40700
13h 45min
Volaris ?
$363
Chicago
San Jose, Costa Rica
Outbound
03/02/25
1 Stopover (BOG)
AV0263, AV0692
10h 40min
Return
03/07/25
1 Stopover (BOG)
AV0693, AV0262
10h 00min
Avianca ?
$377
Chicago
San Jose, Costa Rica
Outbound
02/19/25
1 Stopover (BOG)
AV0263, AV0696
19h 45min
Return
03/10/25
1 Stopover (BOG)
AV0693, AV0262
10h 00min
Avianca ?
$401
Chicago
San Jose, Costa Rica
Outbound
02/19/25
1 Stopover (MIA, FLL)
NK1843, NK0335
29h 33min
Return
03/10/25
3 Stopovers (MEX, CUN, QRO)
AM0691, AM0550, Y43516, Y47890
33h 02min
Spirit Airlines ?
$501
Chicago
San Jose, Costa Rica
Outbound
02/19/25
1 Stopover (FLL)
NK0001, NK1755
08h 39min
Return
03/10/25
1 Stopover (MEX)
AM0657, AM0682
16h 56min
Spirit Airlines
$581
Prices based on recent searches, subject to last-minute changes
Page 1 / 3

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 %

Flight information: Chicago - San Jose, Costa Rica

Roundtrip from $307.22
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 destinations with a similar price
Flight destinations with a similar price
Privacy | | About / Terms and conditions
* Prices may vary, please check the travel details given by the online travel agency before booking. Prices include taxes.