Find Cheap Flights from Chicago Midway to Central America

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 Chicago Midway to Central America

(Round-trip)
Depart: Sat Apr 29 2017 Return: Wed May 3 2017 Trip spans 5 days
Delta
Delta
MDW
SJO
6h 43m
1 stop
SJO
MDW
8h 20m
1 stop
Depart: Wed Oct 4 2017 Return: Sat Oct 14 2017 Trip spans 11 days
Volaris
Volaris
MDW
GUA
19h 05m
1 stop
GUA
MDW
21h 09m
1 stop
Depart: Fri May 12 2017 Return: Wed May 17 2017 Trip spans 6 days
Delta
Delta
MDW
SJO
13h 47m
1 stop
SJO
MDW
11h 55m
1 stop
Depart: Wed May 3 2017 Return: Wed May 10 2017 Trip spans 8 days
Delta
Delta
MDW
SJO
9h 02m
1 stop
SJO
MDW
8h 20m
1 stop
Depart: Thu Jun 1 2017 Return: Thu Jun 8 2017 Trip spans 8 days
Delta
Delta
MDW
SJO
9h 02m
1 stop
SJO
MDW
9h 12m
1 stop
Depart: Sun Oct 8 2017 Return: Sun Oct 15 2017 Trip spans 8 days
Volaris
Volaris
MDW
SJO
18h 20m
1 stop
SJO
MDW
21h 53m
1 stop
Depart: Fri Jun 9 2017 Return: Tue Jun 13 2017 Trip spans 5 days
Delta
Delta
MDW
SJO
6h 57m
1 stop
SJO
MDW
8h 57m
1 stop
Depart: Mon Sep 18 2017 Return: Tue Sep 26 2017 Trip spans 9 days
Volaris
Volaris
MDW
GUA
19h 05m
1 stop
GUA
MDW
21h 09m
1 stop
Depart: Thu Sep 14 2017 Return: Thu Sep 21 2017 Trip spans 8 days
Delta
Delta
MDW
SJO
6h 46m
1 stop
SJO
MDW
8h 53m
1 stop
Depart: Thu May 25 2017 Return: Mon Jun 5 2017 Trip spans 12 days
Volaris
Volaris
MDW
SJO
18h 20m
1 stop
SJO
MDW
21h 53m
1 stop
Depart: Tue Aug 15 2017 Return: Thu Aug 24 2017 Trip spans 10 days
Delta
Delta
MDW
SJO
14h 40m
1 stop
SJO
MDW
8h 53m
1 stop
Depart: Mon Jul 17 2017 Return: Sat Aug 26 2017 Trip spans 41 days
Volaris
Volaris
MDW
GUA
19h 05m
1 stop
GUA
MDW
21h 09m
1 stop
Depart: Mon Oct 2 2017 Return: Wed Oct 18 2017 Trip spans 17 days
Delta
Delta
MDW
SJO
7h 00m
1 stop
SJO
MDW
8h 53m
1 stop
Depart: Thu Apr 27 2017 Return: Wed May 10 2017 Trip spans 14 days
Delta
Delta
MDW
GUA
13h 19m
1 stop
GUA
MDW
7h 55m
1 stop
Depart: Sat Apr 29 2017 Return: Tue May 2 2017 Trip spans 4 days
Delta
Delta
MDW
GUA
14h 39m
1 stop
GUA
MDW
7h 55m
1 stop
Depart: Tue Jun 20 2017 Return: Sun Jul 2 2017 Trip spans 13 days
Volaris
Volaris
MDW
SJO
18h 20m
1 stop
SJO
MDW
21h 53m
1 stop
Depart: Thu May 4 2017 Return: Mon May 15 2017 Trip spans 12 days
Delta
Delta
MDW
GUA
6h 25m
1 stop
GUA
MDW
11h 00m
1 stop
Depart: Mon Jul 3 2017 Return: Tue Jul 11 2017 Trip spans 9 days
Volaris
Volaris
MDW
GUA
19h 05m
1 stop
GUA
MDW
21h 09m
1 stop
Depart: Sat May 6 2017 Return: Tue May 9 2017 Trip spans 4 days
Delta
Delta
MDW
GUA
13h 15m
1 stop
GUA
MDW
13h 20m
1 stop
Depart: Sat May 20 2017 Return: Sun May 28 2017 Trip spans 9 days
Delta
Delta
MDW
GUA
7h 55m
1 stop
GUA
MDW
8h 15m
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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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,
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Airports
Origin

Chicago
$298
Destination

Guatemala City
$400
San Jose
$298