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
Students
under 26
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: Fri May 5 2017 Return: Mon May 8 2017 Trip spans 4 days
Delta
Delta
SJO
MDW
13h 49m
1 stop
MDW
SJO
6h 55m
1 stop
Depart: Fri Jun 2 2017 Return: Sun Jun 4 2017 Trip spans 3 days
Volaris
Volaris
SJO
MDW
22h 10m
1 stop
MDW
SJO
18h 55m
1 stop
Depart: Sat May 6 2017 Return: Sat May 13 2017 Trip spans 8 days
Delta
Delta
SJO
MDW
8h 57m
1 stop
MDW
SJO
6h 59m
1 stop
Depart: Mon Jul 31 2017 Return: Wed Aug 9 2017 Trip spans 10 days
Delta
Delta
SJO
MDW
28h 08m
2 stops
MDW
SJO
6h 46m
1 stop
Depart: Tue Apr 11 2017 Return: Tue Apr 18 2017 Trip spans 8 days
Delta
Delta
SJO
MDW
18h 26m
1 stop
MDW
SJO
25h 46m
2 stops
Depart: Tue Feb 14 2017 Return: Tue Feb 21 2017 Trip spans 8 days
Delta
Delta
BZE
MDW
7h 02m
1 stop
MDW
BZE
6h 04m
1 stop
Depart: Sat Jun 3 2017 Return: Wed Jun 7 2017 Trip spans 5 days
Volaris
Volaris
GUA
MDW
21h 55m
1 stop
MDW
GUA
19h 05m
1 stop
Depart: Thu Jul 13 2017 Return: Mon Jul 17 2017 Trip spans 5 days
Volaris
Volaris
GUA
MDW
21h 55m
1 stop
MDW
GUA
19h 05m
1 stop
Depart: Fri Feb 3 2017 Return: Thu Feb 9 2017 Trip spans 7 days
Delta
Delta
SJO
MDW
8h 21m
1 stop
MDW
SJO
8h 41m
1 stop
Depart: Thu Mar 16 2017 Return: Sun Mar 19 2017 Trip spans 4 days
Delta
Delta
SJO
MDW
12h 15m
1 stop
MDW
SJO
14h 02m
1 stop
Depart: Thu Feb 2 2017 Return: Wed Feb 22 2017 Trip spans 21 days
Volaris
Volaris
SJO
MDW
22h 02m
1 stop
MDW
SJO
18h 15m
1 stop
Depart: Wed Feb 1 2017 Return: Tue Feb 7 2017 Trip spans 7 days
Delta
Delta
GUA
MDW
8h 14m
1 stop
MDW
GUA
6h 42m
1 stop
Depart: Thu Jan 26 2017 Return: Sat Feb 11 2017 Trip spans 17 days
Volaris
Volaris
SJO
MDW
22h 07m
1 stop
MDW
SJO
18h 15m
1 stop
Depart: Wed Feb 22 2017 Return: Mon Feb 27 2017 Trip spans 6 days
Delta
Delta
GUA
MDW
8h 15m
1 stop
MDW
GUA
8h 15m
1 stop
Depart: Tue Apr 11 2017 Return: Tue May 16 2017 Trip spans 36 days
Delta
Delta
GUA
MDW
10h 57m
1 stop
MDW
GUA
7h 16m
1 stop
Depart: Mon May 1 2017 Return: Mon May 15 2017 Trip spans 15 days
Delta
Delta
GUA
MDW
7h 50m
1 stop
MDW
GUA
6h 43m
1 stop
Depart: Mon Jan 30 2017 Return: Mon Feb 6 2017 Trip spans 8 days
Delta
Delta
GUA
MDW
8h 14m
1 stop
MDW
GUA
14h 50m
1 stop
Depart: Thu Mar 9 2017 Return: Wed Mar 15 2017 Trip spans 6 days
Delta
Delta
GUA
MDW
19h 23m
1 stop
MDW
GUA
6h 57m
1 stop
Depart: Thu Apr 13 2017 Return: Sun Apr 23 2017 Trip spans 11 days
Delta
Delta
BZE
MDW
20h 45m
1 stop
MDW
BZE
5h 55m
1 stop
Depart: Sun Jun 25 2017 Return: Tue Jul 4 2017 Trip spans 10 days
Delta
Delta
GUA
MDW
10h 14m
1 stop
MDW
GUA
6h 48m
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
$428
Belize City
$375
San Jose
$316
Destination

Chicago
$316