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: Mon Mar 5 2018 Return: Tue Mar 13 2018 Trip spans 8 days
Delta
Delta
GUA
MDW
8h 32m
1 stop
MDW
GUA
7h 16m
1 stop
Depart: Sat Jan 20 2018 Return: Thu Jan 25 2018 Trip spans 6 days
Aeromexico
Aeromexico
SJO
MDW
16h 08m
2 stops
MDW
SJO
18h 50m
2 stops
Depart: Tue Nov 21 2017 Return: Fri Dec 1 2017 Trip spans 11 days
Volaris
Volaris
GUA
MDW
21h 25m
1 stop
MDW
GUA
18h 48m
1 stop
Depart: Wed May 9 2018 Return: Sun May 13 2018 Trip spans 5 days
Delta
Delta
GUA
MDW
8h 16m
1 stop
MDW
GUA
7h 16m
1 stop
Depart: Sat Jan 27 2018 Return: Sat Feb 3 2018 Trip spans 8 days
Aeromexico
Aeromexico
SJO
MDW
16h 08m
2 stops
MDW
SJO
18h 50m
2 stops
Depart: Fri Jan 26 2018 Return: Wed Feb 7 2018 Trip spans 13 days
Delta
Delta
SJO
MDW
9h 22m
1 stop
MDW
SJO
8h 40m
1 stop
Depart: Thu Jan 25 2018 Return: Mon Jan 29 2018 Trip spans 5 days
Aeromexico
Aeromexico
SJO
MDW
15h 03m
2 stops
MDW
SJO
14h 40m
2 stops
Depart: Fri Jan 26 2018 Return: Sun Feb 4 2018 Trip spans 10 days
Delta
Delta
SJO
MDW
9h 22m
1 stop
MDW
SJO
6h 46m
1 stop
Depart: Thu Dec 28 2017 Return: Mon Jan 1 2018 Trip spans 5 days
Volaris
Volaris
GUA
MDW
21h 25m
1 stop
MDW
GUA
18h 48m
1 stop
Depart: Wed Jan 17 2018 Return: Thu Jan 25 2018 Trip spans 9 days
Aeromexico
Aeromexico
GUA
MDW
22h 22m
2 stops
MDW
GUA
12h 05m
2 stops
Depart: Sun Apr 15 2018 Return: Fri Apr 20 2018 Trip spans 6 days
Delta
Delta
SJO
MDW
9h 17m
1 stop
MDW
SJO
14h 05m
2 stops
Depart: Sat Jan 20 2018 Return: Sun Feb 4 2018 Trip spans 16 days
Aeromexico
Aeromexico
GUA
MDW
15h 23m
2 stops
MDW
GUA
13h 15m
2 stops
Depart: Tue Jan 16 2018 Return: Tue Feb 13 2018 Trip spans 29 days
Delta
Delta
SJO
MDW
12h 25m
2 stops
MDW
SJO
8h 40m
1 stop
Depart: Thu Dec 7 2017 Return: Mon Dec 11 2017 Trip spans 5 days
Volaris
Volaris
GUA
MDW
21h 25m
1 stop
MDW
GUA
18h 48m
1 stop
Depart: Fri Dec 15 2017 Return: Mon Jan 15 2018 Trip spans 32 days
Delta
Delta
MGA
MDW
14h 03m
2 stops
MDW
MGA
8h 35m
1 stop
Depart: Sat Apr 14 2018 Return: Sun Apr 22 2018 Trip spans 9 days
Delta
Delta
MGA
MDW
8h 47m
1 stop
MDW
MGA
8h 00m
1 stop
Depart: Sun Dec 24 2017 Return: Sun Dec 31 2017 Trip spans 8 days
Aeromexico
Aeromexico
GUA
MDW
16h 18m
2 stops
MDW
GUA
30h 05m
2 stops
Depart: Tue Nov 28 2017 Return: Wed Dec 20 2017 Trip spans 23 days
Volaris
Volaris
GUA
MDW
21h 25m
1 stop
MDW
GUA
13h 07m
1 stop
Depart: Sat Dec 2 2017 Return: Wed Dec 6 2017 Trip spans 5 days
Aeromexico
Aeromexico
SJO
MDW
15h 25m
2 stops
MDW
SJO
14h 20m
2 stops
Depart: Fri Nov 24 2017 Return: Mon Nov 27 2017 Trip spans 4 days
Delta
Delta
PTY
MDW
14h 38m
1 stop
MDW
PTY
9h 58m
2 stops
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Guatemala City
$449
Panama City
$530
Managua
$512
San Jose
$458
Destination

Chicago
$449