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: Thu Jun 1 2017 Return: Thu Jun 8 2017 Trip spans 8 days
Delta
Delta
MDW
SJO
9h 02m
1 stop
SJO
MDW
14h 15m
1 stop
Depart: Wed Oct 4 2017 Return: Thu Oct 12 2017 Trip spans 9 days
Volaris
Volaris
MDW
GUA
19h 05m
1 stop
GUA
MDW
21h 09m
1 stop
Depart: Sat Nov 18 2017 Return: Fri Nov 24 2017 Trip spans 7 days
Hahn Air Systems
Hahn Air Systems
MDW
SJO
17h 20m
1 stop
SJO
MDW
22h 53m
1 stop
Depart: Thu Nov 16 2017 Return: Mon Nov 20 2017 Trip spans 5 days
Major Airline
Major Airline
MDW
LIR
4h 18m
nonstop
LIR
MDW
4h 18m
nonstop
Depart: Thu Sep 14 2017 Return: Thu Sep 21 2017 Trip spans 8 days
Delta
Delta
MDW
SJO
6h 46m
1 stop
SJO
MDW
9h 07m
1 stop
Depart: Thu Oct 12 2017 Return: Tue Oct 17 2017 Trip spans 6 days
Delta
Delta
MDW
SJO
6h 46m
1 stop
SJO
MDW
9h 02m
1 stop
Depart: Sun Oct 1 2017 Return: Fri Oct 6 2017 Trip spans 6 days
Volaris
Volaris
MDW
SJO
18h 20m
1 stop
SJO
MDW
21h 53m
1 stop
Depart: Tue Jun 6 2017 Return: Tue Jun 13 2017 Trip spans 8 days
Delta
Delta
MDW
GUA
13h 15m
1 stop
GUA
MDW
7h 14m
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: Wed Jul 26 2017 Return: Tue Aug 8 2017 Trip spans 14 days
Delta
Delta
MDW
GUA
13h 48m
1 stop
GUA
MDW
7h 07m
1 stop
Depart: Wed Oct 4 2017 Return: Sun Oct 8 2017 Trip spans 5 days
Delta
Delta
MDW
GUA
7h 16m
1 stop
GUA
MDW
8h 48m
1 stop
Depart: Thu Jul 6 2017 Return: Sun Jul 30 2017 Trip spans 25 days
Hahn Air Systems
Hahn Air Systems
MDW
SJO
18h 20m
1 stop
SJO
MDW
21h 53m
1 stop
Depart: Tue Oct 3 2017 Return: Sun Oct 8 2017 Trip spans 6 days
Volaris
Volaris
MDW
SJO
18h 20m
1 stop
SJO
MDW
21h 53m
1 stop
Depart: Sat Jun 3 2017 Return: Sun Jun 18 2017 Trip spans 16 days
Delta
Delta
MDW
GUA
13h 15m
1 stop
GUA
MDW
15h 02m
1 stop
Depart: Tue Nov 21 2017 Return: Sun Nov 26 2017 Trip spans 6 days
Hahn Air Systems
Hahn Air Systems
MDW
SJO
17h 20m
1 stop
SJO
MDW
22h 53m
1 stop
Depart: Tue Aug 22 2017 Return: Sun Aug 27 2017 Trip spans 6 days
Major Airline
Major Airline
MDW
LIR
5h 18m
1 stop
LIR
MDW
3h 18m
1 stop
Depart: Wed May 31 2017 Return: Tue Jun 6 2017 Trip spans 7 days
Volaris
Volaris
MDW
GUA
19h 05m
1 stop
GUA
MDW
21h 27m
1 stop
Depart: Tue Jul 25 2017 Return: Fri Aug 4 2017 Trip spans 11 days
Delta
Delta
MDW
GUA
9h 08m
1 stop
GUA
MDW
11h 06m
1 stop
Depart: Thu Jul 13 2017 Return: Fri Jul 21 2017 Trip spans 9 days
Hahn Air Systems
Hahn Air Systems
MDW
SJO
18h 20m
1 stop
SJO
MDW
21h 53m
1 stop
Depart: Tue Aug 1 2017 Return: Tue Aug 8 2017 Trip spans 8 days
Delta
Delta
MDW
GUA
7h 18m
1 stop
GUA
MDW
7h 07m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Here's why:

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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
$402
Destination

Guatemala City
$413
Liberia
$637
San Jose
$402