Find Cheap Flights from Costa Rica to Chicago

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Costa Rica to Chicago

(Round-trip)
Depart: Thu Oct 26 2017 Return: Mon Oct 30 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJO
ORD
10h 23m
1 stop
ORD
SJO
7h 20m
1 stop
Depart: Fri Jan 26 2018 Return: Wed Feb 7 2018 Trip spans 13 days
Interjet
Interjet
SJO
ORD
16h 20m
1 stop
ORD
SJO
9h 55m
1 stop
Depart: Fri Nov 10 2017 Return: Tue Nov 14 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
SJO
ORD
8h 21m
1 stop
ORD
SJO
6h 50m
1 stop
Depart: Thu Oct 5 2017 Return: Wed Oct 11 2017 Trip spans 7 days
Delta
Delta
SJO
MDW
8h 32m
1 stop
MDW
SJO
10h 42m
1 stop
Depart: Fri Sep 15 2017 Return: Sat Sep 23 2017 Trip spans 9 days
Avianca
Avianca
SJO
ORD
19h 40m
1 stop
ORD
SJO
6h 55m
1 stop
Depart: Tue Oct 3 2017 Return: Wed Oct 11 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
SJO
ORD
7h 39m
1 stop
ORD
SJO
7h 20m
1 stop
Depart: Thu Aug 24 2017 Return: Tue Sep 12 2017 Trip spans 20 days
United
United
SJO
ORD
18h 24m
1 stop
ORD
SJO
13h 42m
1 stop
Depart: Fri Feb 9 2018 Return: Mon Feb 12 2018 Trip spans 4 days
Interjet
Interjet
SJO
ORD
16h 20m
1 stop
ORD
SJO
22h 15m
1 stop
Depart: Fri Sep 15 2017 Return: Sat Sep 23 2017 Trip spans 9 days
Hahn Air Systems
Hahn Air Systems
SJO
MDW
23h 29m
1 stop
MDW
SJO
26h 55m
1 stop
Depart: Tue Sep 26 2017 Return: Thu Sep 28 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
SJO
ORD
10h 23m
1 stop
ORD
SJO
19h 12m
1 stop
Depart: Fri Oct 6 2017 Return: Mon Oct 9 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
SJO
ORD
20h 14m
1 stop
ORD
SJO
7h 20m
1 stop
Depart: Tue Nov 28 2017 Return: Mon Dec 4 2017 Trip spans 7 days
Interjet
Interjet
SJO
ORD
16h 10m
1 stop
ORD
SJO
12h 00m
1 stop
Depart: Wed Dec 27 2017 Return: Wed Jan 17 2018 Trip spans 22 days
Avianca
Avianca
SJO
ORD
19h 40m
1 stop
ORD
SJO
6h 55m
1 stop
Depart: Mon Nov 20 2017 Return: Tue Dec 5 2017 Trip spans 16 days
Delta
Delta
SJO
MDW
14h 50m
1 stop
MDW
SJO
6h 46m
1 stop
Depart: Fri Oct 6 2017 Return: Wed Oct 11 2017 Trip spans 6 days
Delta
Delta
SJO
MDW
8h 32m
1 stop
MDW
SJO
10h 42m
1 stop
Depart: Tue Sep 26 2017 Return: Thu Sep 28 2017 Trip spans 3 days
Delta
Delta
SJO
MDW
9h 35m
1 stop
MDW
SJO
6h 50m
1 stop
Depart: Thu Nov 16 2017 Return: Thu Nov 23 2017 Trip spans 8 days
Delta
Delta
SJO
MDW
9h 50m
1 stop
MDW
SJO
6h 46m
1 stop
Depart: Tue Nov 28 2017 Return: Tue Dec 5 2017 Trip spans 8 days
Delta
Delta
SJO
MDW
10h 01m
1 stop
MDW
SJO
6h 46m
1 stop
Depart: Fri Feb 9 2018 Return: Tue Feb 13 2018 Trip spans 5 days
Delta
Delta
SJO
MDW
13h 03m
1 stop
MDW
SJO
13h 40m
2 stops
Depart: Fri Jan 26 2018 Return: Wed Feb 7 2018 Trip spans 13 days
Delta
Delta
SJO
MDW
9h 22m
1 stop
MDW
SJO
14h 40m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

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Airports
Origin

San Jose
$302
Destination

Chicago
only $302
only $436
Airlines Airline reviews

2 travelers who booked a flight from San Jose to Chicago rated their chosen airlines with an average of 9.8.

Overall
10.0
Boarding
10.0
Crew
10.0
Comfort
9.0
Food
10.0
Entertainment
10.0