Find Cheap Flights from Chicago Midway to Costa Rica

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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Book cheap flights from Chicago Midway to Costa Rica

(Round-trip)
Depart: Thu Jun 1 2017 Return: Thu Jun 8 2017 Trip spans 8 days
Delta
Delta
MDW
8:05a
SJO
5:07p
9h 02m
1 stop
SJO
3:05a
MDW
5:20p
14h 15m
1 stop
Depart: Thu Aug 31 2017 Return: Mon Sep 4 2017 Trip spans 5 days
Volaris
Volaris
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Sun Jun 11 2017 Return: Sun Jun 18 2017 Trip spans 8 days
Hahn Air Systems
Hahn Air Systems
MDW
1:31p
SJO
7:49a
18h 18m
1 stop
SJO
8:04a
MDW
6:15a
22h 11m
1 stop
Depart: Thu Oct 12 2017 Return: Tue Oct 17 2017 Trip spans 6 days
Delta
Delta
MDW
2:00a
SJO
8:46a
6h 46m
1 stop
SJO
9:00a
MDW
6:02p
9h 02m
1 stop
Depart: Sat Jun 10 2017 Return: Wed Jun 14 2017 Trip spans 5 days
Delta
Delta
MDW
4:45a
SJO
5:07p
12h 22m
2 stops
SJO
3:00a
MDW
12:24p
9h 24m
1 stop
Depart: Sun Oct 8 2017 Return: Sun Oct 15 2017 Trip spans 8 days
Volaris
Volaris
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Sat Oct 7 2017 Return: Wed Oct 11 2017 Trip spans 5 days
Volaris
Volaris
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Tue May 30 2017 Return: Tue Jun 6 2017 Trip spans 8 days
Delta
Delta
MDW
8:05a
SJO
5:07p
9h 02m
1 stop
SJO
9:00a
MDW
5:20p
8h 20m
1 stop
Depart: Thu Jun 22 2017 Return: Mon Jun 26 2017 Trip spans 5 days
Hahn Air Systems
Hahn Air Systems
MDW
1:31p
SJO
7:49a
18h 18m
1 stop
SJO
8:04a
MDW
6:15a
22h 11m
1 stop
Depart: Mon Aug 21 2017 Return: Tue Aug 29 2017 Trip spans 9 days
Delta
Delta
MDW
2:00a
SJO
8:46a
6h 46m
1 stop
SJO
9:00a
MDW
6:02p
9h 02m
1 stop
Depart: Sun Oct 22 2017 Return: Sun Oct 29 2017 Trip spans 8 days
Volaris
Volaris
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Tue Jun 27 2017 Return: Wed Jul 5 2017 Trip spans 9 days
Hahn Air Systems
Hahn Air Systems
MDW
1:31p
SJO
7:49a
18h 18m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Thu Sep 7 2017 Return: Mon Sep 11 2017 Trip spans 5 days
Delta
Delta
MDW
2:00a
SJO
8:46a
6h 46m
1 stop
SJO
3:20a
MDW
6:07p
14h 47m
1 stop
Depart: Sun Aug 13 2017 Return: Mon Aug 21 2017 Trip spans 9 days
Volaris
Volaris
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
6:15a
22h 11m
1 stop
Depart: Thu Jun 29 2017 Return: Sun Jul 2 2017 Trip spans 4 days
Hahn Air Systems
Hahn Air Systems
MDW
1:31p
SJO
7:49a
18h 18m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Wed Sep 13 2017 Return: Wed Sep 20 2017 Trip spans 8 days
Delta
Delta
MDW
8:00a
SJO
4:40p
8h 40m
1 stop
SJO
9:00a
MDW
6:07p
9h 07m
1 stop
Depart: Thu Oct 26 2017 Return: Mon Oct 30 2017 Trip spans 5 days
Volaris
Volaris
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Thu Jul 6 2017 Return: Mon Jul 10 2017 Trip spans 5 days
Hahn Air Systems
Hahn Air Systems
MDW
1:29p
SJO
7:49a
18h 20m
1 stop
SJO
8:04a
MDW
5:57a
21h 53m
1 stop
Depart: Wed Sep 20 2017 Return: Wed Oct 4 2017 Trip spans 15 days
Delta
Delta
MDW
6:10a
SJO
4:40p
10h 30m
1 stop
SJO
9:00a
MDW
6:07p
9h 07m
1 stop
Depart: Sun Nov 19 2017 Return: Sun Nov 26 2017 Trip spans 8 days
Hahn Air Systems
Hahn Air Systems
MDW
12:29p
SJO
5:49a
17h 20m
1 stop
SJO
7:04a
MDW
5:57a
22h 53m
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.

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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

Chicago
$402
Destination

San Jose
$402