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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Book cheap flights from Chicago Midway to Central America

(Round-trip)
Depart: Tue Jan 23 2018 Return: Tue Jan 30 2018 Trip spans 8 days
Delta
Delta
MDW
SJO
7h 07m
1 stop
SJO
MDW
9h 24m
1 stop
Depart: Thu Feb 1 2018 Return: Thu Feb 15 2018 Trip spans 15 days
Multiple Airlines
Multiple Airlines
MDW
SJO
24h 46m
1 stop
SJO
MDW
25h 30m
1 stop
Depart: Mon May 28 2018 Return: Fri Jul 27 2018 Trip spans 61 days
Southwest
Southwest
MDW
SJO
6h 45m
nonstop
SJO
MDW
9h 15m
nonstop
Depart: Tue Mar 6 2018 Return: Sun Mar 11 2018 Trip spans 6 days
Multiple Airlines
Multiple Airlines
MDW
SJO
29h 30m
3 stops
SJO
MDW
34h 14m
3 stops
Depart: Thu Feb 1 2018 Return: Mon Feb 5 2018 Trip spans 5 days
Aeromexico
Aeromexico
MDW
GUA
13h 15m
2 stops
GUA
MDW
14h 18m
2 stops
Depart: Fri Feb 23 2018 Return: Sat Mar 3 2018 Trip spans 9 days
Volaris
Volaris
MDW
GUA
18h 48m
1 stop
GUA
MDW
21h 25m
1 stop
Depart: Mon Feb 5 2018 Return: Tue Feb 13 2018 Trip spans 9 days
Delta
Delta
MDW
SJO
8h 56m
1 stop
SJO
MDW
9h 24m
1 stop
Depart: Wed Mar 21 2018 Return: Fri Apr 6 2018 Trip spans 17 days
Multiple Airlines
Multiple Airlines
MDW
SAL
6h 45m
1 stop
SAL
MDW
9h 08m
1 stop
Depart: Tue Feb 6 2018 Return: Tue Feb 13 2018 Trip spans 8 days
Delta
Delta
MDW
SJO
7h 07m
1 stop
SJO
MDW
9h 24m
1 stop
Depart: Wed Mar 21 2018 Return: Thu Apr 5 2018 Trip spans 16 days
Multiple Airlines
Multiple Airlines
MDW
SAL
6h 45m
1 stop
SAL
MDW
20h 15m
1 stop
Depart: Wed Feb 7 2018 Return: Wed Feb 14 2018 Trip spans 8 days
Delta
Delta
MDW
SJO
8h 56m
1 stop
SJO
MDW
9h 24m
1 stop
Depart: Fri Mar 9 2018 Return: Tue Mar 13 2018 Trip spans 4 days
Volaris
Volaris
MDW
GUA
18h 48m
1 stop
GUA
MDW
21h 25m
1 stop
Depart: Thu Jan 11 2018 Return: Mon Jan 22 2018 Trip spans 12 days
Aeromexico
Aeromexico
MDW
SJO
23h 25m
2 stops
SJO
MDW
15h 03m
2 stops
Depart: Mon Jan 8 2018 Return: Thu Feb 22 2018 Trip spans 46 days
Multiple Airlines
Multiple Airlines
MDW
GUA
7h 16m
1 stop
GUA
MDW
21h 25m
1 stop
Depart: Tue Feb 27 2018 Return: Tue Mar 6 2018 Trip spans 8 days
Delta
Delta
MDW
SJO
10h 00m
1 stop
SJO
MDW
9h 17m
1 stop
Depart: Tue Mar 6 2018 Return: Mon Mar 12 2018 Trip spans 6 days
Delta
Delta
MDW
SJO
8h 05m
1 stop
SJO
MDW
8h 53m
1 stop
Depart: Sun Jan 7 2018 Return: Thu Feb 22 2018 Trip spans 47 days
Multiple Airlines
Multiple Airlines
MDW
GUA
21h 16m
1 stop
GUA
MDW
21h 25m
1 stop
Depart: Tue Feb 6 2018 Return: Wed Feb 14 2018 Trip spans 9 days
Aeromexico
Aeromexico
MDW
SJO
12h 50m
2 stops
SJO
MDW
15h 03m
2 stops
Depart: Tue Mar 20 2018 Return: Wed Mar 21 2018 Trip spans 2 days
Delta
Delta
MDW
SJO
6h 46m
1 stop
SJO
MDW
8h 53m
1 stop
Depart: Sun Mar 11 2018 Return: Sun Mar 18 2018 Trip spans 7 days
Multiple Airlines
Multiple Airlines
MDW
LIR
19h 04m
1 stop
LIR
MDW
9h 22m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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

Chicago
$416
Destination

Guatemala City
$492
Liberia
$568
San Salvador
$450
San Jose
$416