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 Oct 12 2017 Return: Tue Oct 17 2017 Trip spans 6 days
Delta
Delta
MDW
SJO
13h 59m
2 stops
SJO
MDW
8h 32m
1 stop
Depart: Fri Mar 30 2018 Return: Sat Apr 7 2018 Trip spans 9 days
Volaris
Volaris
MDW
GUA
18h 48m
1 stop
GUA
MDW
21h 25m
1 stop
Depart: Wed Oct 25 2017 Return: Tue Nov 14 2017 Trip spans 21 days
Delta
Delta
MDW
SJO
13h 39m
1 stop
SJO
MDW
8h 50m
1 stop
Depart: Thu Dec 7 2017 Return: Thu Dec 14 2017 Trip spans 8 days
Delta
Delta
MDW
SJO
14h 40m
1 stop
SJO
MDW
10h 01m
1 stop
Depart: Mon Jan 22 2018 Return: Thu Feb 1 2018 Trip spans 11 days
Delta
Delta
MDW
SJO
14h 40m
1 stop
SJO
MDW
9h 22m
1 stop
Depart: Fri Mar 23 2018 Return: Thu Mar 29 2018 Trip spans 7 days
Volaris
Volaris
MDW
GUA
18h 48m
1 stop
GUA
MDW
21h 25m
1 stop
Depart: Mon Feb 26 2018 Return: Wed Mar 7 2018 Trip spans 10 days
Delta
Delta
MDW
SJO
10h 30m
1 stop
SJO
MDW
8h 53m
1 stop
Depart: Wed Feb 28 2018 Return: Wed Mar 7 2018 Trip spans 8 days
Delta
Delta
MDW
SJO
13h 20m
1 stop
SJO
MDW
8h 53m
1 stop
Depart: Mon Oct 9 2017 Return: Fri Oct 13 2017 Trip spans 5 days
Delta
Delta
MDW
SJO
13h 39m
1 stop
SJO
MDW
14h 35m
1 stop
Depart: Fri Oct 13 2017 Return: Tue Oct 17 2017 Trip spans 5 days
Delta
Delta
MDW
SJO
6h 53m
1 stop
SJO
MDW
8h 32m
1 stop
Depart: Fri Oct 13 2017 Return: Tue Oct 17 2017 Trip spans 5 days
Delta
Delta
MDW
SJO
6h 53m
1 stop
SJO
MDW
8h 32m
1 stop
Depart: Sat Oct 14 2017 Return: Tue Oct 17 2017 Trip spans 4 days
Delta
Delta
MDW
SJO
11h 51m
2 stops
SJO
MDW
8h 32m
1 stop
Depart: Wed Oct 25 2017 Return: Fri Oct 27 2017 Trip spans 3 days
Delta
Delta
MDW
SJO
13h 39m
1 stop
SJO
MDW
9h 38m
1 stop
Depart: Wed Oct 4 2017 Return: Wed Oct 11 2017 Trip spans 8 days
Delta
Delta
MDW
GUA
6h 59m
1 stop
GUA
MDW
8h 31m
1 stop
Depart: Wed Oct 11 2017 Return: Sun Oct 15 2017 Trip spans 5 days
Delta
Delta
MDW
GUA
6h 59m
1 stop
GUA
MDW
8h 31m
1 stop
Depart: Thu Oct 12 2017 Return: Sun Oct 22 2017 Trip spans 11 days
Delta
Delta
MDW
GUA
6h 59m
1 stop
GUA
MDW
7h 51m
1 stop
Depart: Fri Oct 13 2017 Return: Sun Oct 22 2017 Trip spans 10 days
Delta
Delta
MDW
GUA
6h 59m
1 stop
GUA
MDW
7h 51m
1 stop
Depart: Thu Oct 19 2017 Return: Tue Oct 24 2017 Trip spans 6 days
Delta
Delta
MDW
GUA
6h 59m
1 stop
GUA
MDW
8h 31m
1 stop
Depart: Sun Oct 22 2017 Return: Thu Oct 26 2017 Trip spans 5 days
Delta
Delta
MDW
GUA
6h 59m
1 stop
GUA
MDW
8h 31m
1 stop
Depart: Tue Oct 31 2017 Return: Sun Nov 5 2017 Trip spans 6 days
Delta
Delta
MDW
GUA
6h 59m
1 stop
GUA
MDW
8h 36m
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:

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,
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Airports
Origin

Chicago
$404
Destination

Guatemala City
$420
San Jose
$404