Find Cheap 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: Fri Sep 29 2017 Return: Thu Oct 5 2017 Trip spans 7 days
Delta
Delta
GUA
MDW
8h 48m
1 stop
MDW
GUA
7h 16m
1 stop
Depart: Fri Oct 6 2017 Return: Sun Oct 15 2017 Trip spans 10 days
Volaris
Volaris
SJO
MDW
21h 53m
1 stop
MDW
SJO
18h 20m
1 stop
Depart: Fri Aug 4 2017 Return: Sat Aug 26 2017 Trip spans 23 days
Major Airline
Major Airline
BZE
MDW
2h 20m
2 stops
MDW
BZE
4h 20m
2 stops
Depart: Tue Dec 5 2017 Return: Wed Jan 3 2018 Trip spans 30 days
Delta
Delta
GUA
MDW
8h 27m
1 stop
MDW
GUA
8h 10m
1 stop
Depart: Wed Sep 13 2017 Return: Tue Sep 19 2017 Trip spans 7 days
Volaris
Volaris
SJO
MDW
21h 53m
1 stop
MDW
SJO
18h 20m
1 stop
Depart: Thu Oct 5 2017 Return: Wed Oct 11 2017 Trip spans 7 days
Delta
Delta
SJO
MDW
9h 27m
1 stop
MDW
SJO
6h 46m
1 stop
Depart: Mon Jul 10 2017 Return: Sat Jul 22 2017 Trip spans 13 days
Delta
Delta
GUA
MDW
14h 18m
2 stops
MDW
GUA
13h 48m
1 stop
Depart: Wed Aug 2 2017 Return: Mon Aug 7 2017 Trip spans 6 days
Delta
Delta
GUA
MDW
14h 55m
1 stop
MDW
GUA
11h 50m
2 stops
Depart: Fri Oct 20 2017 Return: Wed Oct 25 2017 Trip spans 6 days
Delta
Delta
GUA
MDW
8h 48m
1 stop
MDW
GUA
7h 16m
1 stop
Depart: Thu Aug 3 2017 Return: Tue Aug 8 2017 Trip spans 6 days
Delta
Delta
SJO
MDW
8h 50m
1 stop
MDW
SJO
6h 50m
1 stop
Depart: Tue Aug 1 2017 Return: Wed Aug 9 2017 Trip spans 9 days
Delta
Delta
MGA
MDW
8h 49m
1 stop
MDW
MGA
7h 00m
1 stop
Depart: Tue Nov 7 2017 Return: Mon Nov 20 2017 Trip spans 14 days
Delta
Delta
MGA
MDW
9h 12m
1 stop
MDW
MGA
6h 30m
1 stop
Depart: Sat Dec 2 2017 Return: Wed Jan 31 2018 Trip spans 61 days
Delta
Delta
MGA
MDW
8h 46m
1 stop
MDW
MGA
10h 25m
1 stop
Depart: Mon Jul 17 2017 Return: Wed Aug 23 2017 Trip spans 38 days
Delta
Delta
BZE
MDW
8h 21m
1 stop
MDW
BZE
6h 02m
1 stop
Depart: Tue Jul 25 2017 Return: Thu Aug 10 2017 Trip spans 17 days
Delta
Delta
GUA
MDW
14h 55m
1 stop
MDW
GUA
10h 58m
1 stop
Depart: Wed Aug 9 2017 Return: Tue Aug 15 2017 Trip spans 7 days
Delta
Delta
GUA
MDW
7h 07m
1 stop
MDW
GUA
13h 28m
1 stop
Depart: Wed Aug 23 2017 Return: Wed Sep 6 2017 Trip spans 15 days
Delta
Delta
GUA
MDW
8h 26m
1 stop
MDW
GUA
7h 16m
1 stop
Depart: Wed Oct 18 2017 Return: Sun Nov 12 2017 Trip spans 26 days
Delta
Delta
GUA
MDW
8h 48m
1 stop
MDW
GUA
7h 16m
1 stop
Depart: Mon Dec 18 2017 Return: Fri Dec 29 2017 Trip spans 12 days
Delta
Delta
GUA
MDW
8h 32m
1 stop
MDW
GUA
14h 00m
1 stop
Depart: Mon Oct 2 2017 Return: Sun Oct 8 2017 Trip spans 7 days
Delta
Delta
SAP
MDW
9h 47m
1 stop
MDW
SAP
6h 10m
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.

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Airports
Origin

Guatemala City
$435
San Pedro Sula
$555
Managua
$512
Belize City
$530
San Jose
$436
Destination

Chicago
$435