Find Deals on 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: Mon May 1 2017 Return: Sat May 6 2017 Trip spans 6 days
Delta
Delta
MDW
SJO
9h 02m
1 stop
SJO
MDW
8h 19m
1 stop
Depart: Wed May 3 2017 Return: Tue May 9 2017 Trip spans 7 days
Volaris
Volaris
MDW
GUA
19h 05m
1 stop
GUA
MDW
21h 09m
1 stop
Depart: Fri Apr 21 2017 Return: Sat Apr 29 2017 Trip spans 9 days
Major Airline
Major Airline
MDW
BZE
4h 20m
nonstop
BZE
MDW
2h 20m
nonstop
Depart: Fri May 5 2017 Return: Fri May 12 2017 Trip spans 8 days
Delta
Delta
MDW
SJO
10h 46m
1 stop
SJO
MDW
14h 15m
1 stop
Depart: Wed Sep 6 2017 Return: Tue Sep 12 2017 Trip spans 7 days
Volaris
Volaris
MDW
GUA
19h 05m
1 stop
GUA
MDW
21h 09m
1 stop
Depart: Mon Apr 24 2017 Return: Tue May 2 2017 Trip spans 9 days
Delta
Delta
MDW
BZE
6h 06m
1 stop
BZE
MDW
7h 10m
1 stop
Depart: Fri Jun 9 2017 Return: Tue Jun 13 2017 Trip spans 5 days
Volaris
Volaris
MDW
GUA
19h 05m
1 stop
GUA
MDW
21h 09m
1 stop
Depart: Fri May 5 2017 Return: Fri May 12 2017 Trip spans 8 days
Delta
Delta
MDW
BZE
5h 53m
1 stop
BZE
MDW
7h 10m
1 stop
Depart: Tue May 16 2017 Return: Fri May 26 2017 Trip spans 11 days
Delta
Delta
MDW
BZE
5h 53m
1 stop
BZE
MDW
7h 10m
1 stop
Depart: Thu Jun 1 2017 Return: Mon Jun 5 2017 Trip spans 5 days
Volaris
Volaris
MDW
SJO
18h 20m
1 stop
SJO
MDW
21h 53m
1 stop
Depart: Tue Jul 25 2017 Return: Wed Aug 2 2017 Trip spans 9 days
Delta
Delta
MDW
BZE
5h 55m
1 stop
BZE
MDW
7h 53m
1 stop
Depart: Tue Sep 19 2017 Return: Tue Sep 26 2017 Trip spans 8 days
Delta
Delta
MDW
BZE
5h 55m
1 stop
BZE
MDW
9h 58m
1 stop
Depart: Thu Jun 8 2017 Return: Mon Jun 12 2017 Trip spans 5 days
Volaris
Volaris
MDW
SJO
18h 20m
1 stop
SJO
MDW
21h 53m
1 stop
Depart: Thu May 4 2017 Return: Mon May 8 2017 Trip spans 5 days
Major Airline
Major Airline
MDW
LIR
5h 18m
nonstop
LIR
MDW
3h 18m
nonstop
Depart: Mon Sep 25 2017 Return: Mon Oct 2 2017 Trip spans 8 days
Delta
Delta
MDW
BZE
5h 55m
1 stop
BZE
MDW
10h 03m
1 stop
Depart: Sun Jun 11 2017 Return: Fri Jun 16 2017 Trip spans 6 days
Volaris
Volaris
MDW
SJO
18h 20m
1 stop
SJO
MDW
21h 53m
1 stop
Depart: Wed May 10 2017 Return: Sun May 14 2017 Trip spans 5 days
Delta
Delta
MDW
SJO
6h 45m
1 stop
SJO
MDW
14h 15m
1 stop
Depart: Sat Aug 26 2017 Return: Wed Aug 30 2017 Trip spans 5 days
Volaris
Volaris
MDW
SJO
18h 20m
1 stop
SJO
MDW
21h 53m
1 stop
Depart: Wed Aug 30 2017 Return: Wed Sep 6 2017 Trip spans 8 days
Delta
Delta
MDW
SJO
6h 46m
1 stop
SJO
MDW
8h 53m
1 stop
Depart: Sun Sep 3 2017 Return: Fri Sep 8 2017 Trip spans 6 days
Delta
Delta
MDW
SJO
6h 46m
1 stop
SJO
MDW
8h 53m
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,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Chicago
$350
Destination

Guatemala City
$387
Liberia
$633
Belize City
$375
San Jose
$350