Find Cheap Flights from Costa Rica to Chicago Midway

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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Costa Rica to Chicago Midway

(Round-trip)
Depart: Thu Aug 24 2017 Return: Tue Aug 29 2017 Trip spans 6 days
Delta
Delta
SJO
9:00a
MDW
5:53p
8h 53m
1 stop
MDW
2:00a
SJO
8:46a
6h 46m
1 stop
Depart: Mon Aug 28 2017 Return: Tue Aug 29 2017 Trip spans 2 days
Volaris
Volaris
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
Depart: Wed May 17 2017 Return: Tue May 23 2017 Trip spans 7 days
Delta
Delta
SJO
3:05a
MDW
3:00p
11h 55m
1 stop
MDW
5:16a
SJO
5:07p
11h 51m
2 stops
Depart: Wed Aug 30 2017 Return: Sun Sep 3 2017 Trip spans 5 days
Delta
Delta
SJO
9:00a
MDW
5:53p
8h 53m
1 stop
MDW
2:00a
SJO
8:46a
6h 46m
1 stop
Depart: Wed Sep 13 2017 Return: Tue Sep 19 2017 Trip spans 7 days
Volaris
Volaris
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
Depart: Mon Sep 11 2017 Return: Tue Sep 19 2017 Trip spans 9 days
Volaris
Volaris
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
Depart: Tue May 23 2017 Return: Sun May 28 2017 Trip spans 6 days
Delta
Delta
SJO
3:05a
MDW
3:00p
11h 55m
1 stop
MDW
5:16a
SJO
5:07p
11h 51m
2 stops
Depart: Wed Oct 11 2017 Return: Sun Oct 15 2017 Trip spans 5 days
Volaris
Volaris
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
Depart: Wed Aug 2 2017 Return: Tue Aug 8 2017 Trip spans 7 days
Delta
Delta
SJO
3:20a
MDW
5:53p
14h 33m
1 stop
MDW
2:00a
SJO
8:46a
6h 46m
1 stop
Depart: Thu Sep 14 2017 Return: Tue Sep 19 2017 Trip spans 6 days
Delta
Delta
SJO
9:00a
MDW
5:53p
8h 53m
1 stop
MDW
2:00a
SJO
8:46a
6h 46m
1 stop
Depart: Fri Sep 15 2017 Return: Sun Sep 17 2017 Trip spans 3 days
Volaris
Volaris
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
Depart: Fri Oct 6 2017 Return: Wed Oct 11 2017 Trip spans 6 days
Delta
Delta
SJO
3:20a
MDW
3:43p
12h 23m
1 stop
MDW
2:00a
SJO
8:46a
6h 46m
1 stop
Depart: Sun Sep 10 2017 Return: Sun Sep 17 2017 Trip spans 8 days
Volaris
Volaris
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
Depart: Mon May 15 2017 Return: Wed May 17 2017 Trip spans 3 days
Delta
Delta
SJO
3:05a
MDW
5:20p
14h 15m
1 stop
MDW
2:55a
SJO
5:07p
14h 12m
2 stops
Depart: Wed Aug 16 2017 Return: Sun Sep 3 2017 Trip spans 19 days
Volaris
Volaris
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
Depart: Thu May 25 2017 Return: Tue May 30 2017 Trip spans 6 days
Delta
Delta
SJO
3:05a
MDW
3:00p
11h 55m
1 stop
MDW
2:00a
SJO
8:45a
6h 45m
1 stop
Depart: Fri Aug 25 2017 Return: Sat Sep 2 2017 Trip spans 9 days
Volaris
Volaris
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
Depart: Thu Jun 1 2017 Return: Sat Jun 3 2017 Trip spans 3 days
Delta
Delta
SJO
3:05a
MDW
1:45p
10h 40m
1 stop
MDW
4:45a
SJO
5:07p
12h 22m
2 stops
Depart: Sun May 7 2017 Return: Thu May 18 2017 Trip spans 12 days
Volaris
Volaris
SJO
8:04a
MDW
6:40a
22h 36m
1 stop
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
Depart: Fri Jun 2 2017 Return: Sun Jun 4 2017 Trip spans 3 days
Delta
Delta
SJO
3:05a
MDW
12:17p
9h 12m
1 stop
MDW
6:21a
SJO
5:07p
10h 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
$394
Destination

Chicago
$394