Find Deals on Flights from Central America to Chicago Midway

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 Central America to Chicago Midway

(Round-trip)
Depart: Wed May 17 2017 Return: Sat May 20 2017 Trip spans 4 days
Delta
Delta
SJO
MDW
8h 20m
1 stop
MDW
SJO
8h 03m
1 stop
Depart: Wed Jun 7 2017 Return: Sun Jun 11 2017 Trip spans 5 days
Volaris
Volaris
SJO
MDW
21h 53m
1 stop
MDW
SJO
18h 20m
1 stop
Depart: Wed May 3 2017 Return: Wed May 17 2017 Trip spans 15 days
Delta
Delta
SJO
MDW
9h 12m
1 stop
MDW
SJO
6h 45m
1 stop
Depart: Fri Apr 28 2017 Return: Mon May 1 2017 Trip spans 4 days
Delta
Delta
PTY
MDW
14h 10m
1 stop
MDW
PTY
14h 35m
2 stops
Depart: Fri Sep 15 2017 Return: Sun Sep 17 2017 Trip spans 3 days
Volaris
Volaris
SJO
MDW
21h 53m
1 stop
MDW
SJO
18h 20m
1 stop
Depart: Thu May 25 2017 Return: Sun Jun 4 2017 Trip spans 11 days
Delta
Delta
PTY
MDW
9h 02m
1 stop
MDW
PTY
7h 20m
1 stop
Depart: Thu Aug 10 2017 Return: Mon Aug 14 2017 Trip spans 5 days
Volaris
Volaris
GUA
MDW
21h 09m
1 stop
MDW
GUA
19h 05m
1 stop
Depart: Wed Apr 12 2017 Return: Wed Apr 19 2017 Trip spans 8 days
Delta
Delta
GUA
MDW
7h 59m
1 stop
MDW
GUA
7h 16m
1 stop
Depart: Mon Jul 3 2017 Return: Tue Jul 11 2017 Trip spans 9 days
Volaris
Volaris
SJO
MDW
21h 53m
1 stop
MDW
SJO
18h 20m
1 stop
Depart: Tue May 2 2017 Return: Wed May 17 2017 Trip spans 16 days
Delta
Delta
GUA
MDW
7h 55m
1 stop
MDW
GUA
6h 25m
1 stop
Depart: Thu Jul 13 2017 Return: Mon Jul 17 2017 Trip spans 5 days
Volaris
Volaris
GUA
MDW
21h 09m
1 stop
MDW
GUA
19h 05m
1 stop
Depart: Fri May 19 2017 Return: Mon May 22 2017 Trip spans 4 days
Delta
Delta
GUA
MDW
7h 55m
1 stop
MDW
GUA
6h 25m
1 stop
Depart: Tue Jun 6 2017 Return: Wed Aug 2 2017 Trip spans 58 days
Delta
Delta
GUA
MDW
7h 55m
1 stop
MDW
GUA
7h 16m
1 stop
Depart: Fri Jul 21 2017 Return: Tue Jul 25 2017 Trip spans 5 days
Volaris
Volaris
SJO
MDW
21h 53m
1 stop
MDW
SJO
18h 20m
1 stop
Depart: Thu Aug 3 2017 Return: Tue Aug 8 2017 Trip spans 6 days
Delta
Delta
SJO
MDW
14h 33m
1 stop
MDW
SJO
6h 46m
1 stop
Depart: Mon Jul 24 2017 Return: Sun Aug 6 2017 Trip spans 14 days
Volaris
Volaris
SJO
MDW
21h 53m
1 stop
MDW
SJO
18h 20m
1 stop
Depart: Mon May 15 2017 Return: Mon May 29 2017 Trip spans 15 days
Delta
Delta
BZE
MDW
9h 30m
1 stop
MDW
BZE
5h 53m
1 stop
Depart: Mon Aug 7 2017 Return: Tue Aug 15 2017 Trip spans 9 days
Delta
Delta
GUA
MDW
12h 01m
1 stop
MDW
GUA
7h 16m
1 stop
Depart: Mon Apr 24 2017 Return: Mon May 1 2017 Trip spans 8 days
Delta
Delta
SJO
MDW
14h 25m
1 stop
MDW
SJO
6h 45m
1 stop
Depart: Tue Aug 1 2017 Return: Tue Aug 8 2017 Trip spans 8 days
Delta
Delta
SJO
MDW
8h 48m
1 stop
MDW
SJO
6h 46m
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.

We compile tonnes of data for you
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

Guatemala City
$449
Panama City
$441
Belize City
$486
San Jose
$391
Destination

Chicago
$391