Find Deals on 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: Wed May 17 2017 Return: Thu May 18 2017 Trip spans 2 days
Copa Airlines
Copa Airlines
SJO
ORD
8h 44m
1 stop
ORD
SJO
11h 11m
1 stop
Depart: Wed Apr 19 2017 Return: Sun Apr 23 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJO
ORD
9h 07m
1 stop
ORD
SJO
7h 35m
1 stop
Depart: Wed May 17 2017 Return: Sat May 20 2017 Trip spans 4 days
Delta
Delta
SJO
MDW
8h 20m
1 stop
MDW
SJO
8h 03m
1 stop
Depart: Wed Jun 7 2017 Return: Sun Jun 11 2017 Trip spans 5 days
Volaris
Volaris
SJO
MDW
21h 53m
1 stop
MDW
SJO
18h 20m
1 stop
Depart: Thu May 4 2017 Return: Mon May 8 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJO
ORD
10h 24m
1 stop
ORD
SJO
19h 15m
1 stop
Depart: Fri Jun 2 2017 Return: Tue Jun 20 2017 Trip spans 19 days
Spirit Airlines
Spirit Airlines
SJO
ORD
8h 45m
1 stop
ORD
SJO
7h 19m
1 stop
Depart: Fri Sep 15 2017 Return: Sun Sep 17 2017 Trip spans 3 days
Copa Airlines
Copa Airlines
SJO
ORD
29h 35m
1 stop
ORD
SJO
11h 50m
1 stop
Depart: Fri Mar 31 2017 Return: Fri Apr 7 2017 Trip spans 8 days
Major Airline
Major Airline
SJO
ORD
10h 29m
nonstop
ORD
SJO
8h 15m
nonstop
Depart: Wed May 3 2017 Return: Wed May 17 2017 Trip spans 15 days
Delta
Delta
SJO
MDW
9h 12m
1 stop
MDW
SJO
6h 45m
1 stop
Depart: Sun Apr 9 2017 Return: Fri Apr 14 2017 Trip spans 6 days
Aeromexico
Aeromexico
SJO
ORD
23h 20m
2 stops
ORD
SJO
11h 30m
1 stop
Depart: Tue Aug 1 2017 Return: Wed Aug 9 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
SJO
ORD
8h 45m
1 stop
ORD
SJO
7h 19m
1 stop
Depart: Sat Jun 24 2017 Return: Wed Jun 28 2017 Trip spans 5 days
Copa Airlines
Copa Airlines
SJO
ORD
30h 05m
1 stop
ORD
SJO
26h 35m
1 stop
Depart: Fri Sep 8 2017 Return: Sat Sep 16 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
SJO
ORD
7h 54m
1 stop
ORD
SJO
7h 15m
1 stop
Depart: Fri Sep 15 2017 Return: Sun Sep 17 2017 Trip spans 3 days
Volaris
Volaris
SJO
MDW
21h 53m
1 stop
MDW
SJO
18h 20m
1 stop
Depart: Thu Aug 3 2017 Return: Tue Aug 8 2017 Trip spans 6 days
Delta
Delta
SJO
MDW
14h 33m
1 stop
MDW
SJO
6h 46m
1 stop
Depart: Tue Jul 18 2017 Return: Mon Jul 31 2017 Trip spans 14 days
Spirit Airlines
Spirit Airlines
SJO
ORD
8h 45m
1 stop
ORD
SJO
7h 19m
1 stop
Depart: Mon Jul 3 2017 Return: Tue Jul 11 2017 Trip spans 9 days
Volaris
Volaris
SJO
MDW
21h 53m
1 stop
MDW
SJO
18h 20m
1 stop
Depart: Mon Apr 24 2017 Return: Mon May 1 2017 Trip spans 8 days
Delta
Delta
SJO
MDW
14h 25m
1 stop
MDW
SJO
6h 45m
1 stop
Depart: Fri Jul 21 2017 Return: Wed Jul 26 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJO
ORD
8h 45m
1 stop
ORD
SJO
7h 19m
1 stop
Depart: Tue Aug 1 2017 Return: Tue Aug 8 2017 Trip spans 8 days
Delta
Delta
SJO
MDW
8h 48m
1 stop
MDW
SJO
6h 46m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

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

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

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.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

San Jose
$277
Destination

Chicago
only $277
only $391