Find Cheap Flights from Central America to Chicago

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

(Round-trip)
Depart: Mon Nov 20 2017 Return: Wed Nov 29 2017 Trip spans 10 days
Spirit Airlines
Spirit Airlines
SJO
ORD
10h 06m
1 stop
ORD
SJO
7h 35m
1 stop
Depart: Thu Feb 22 2018 Return: Mon Feb 26 2018 Trip spans 5 days
Interjet
Interjet
SJO
ORD
17h 20m
1 stop
ORD
SJO
9h 55m
1 stop
Depart: Tue Nov 28 2017 Return: Tue Dec 5 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
SJO
ORD
29h 15m
1 stop
ORD
SJO
7h 35m
1 stop
Depart: Tue Dec 12 2017 Return: Sun Feb 4 2018 Trip spans 55 days
JetBlue
JetBlue
SJO
ORD
8h 21m
1 stop
ORD
SJO
7h 24m
1 stop
Depart: Wed Nov 22 2017 Return: Mon Nov 27 2017 Trip spans 6 days
Aeromexico
Aeromexico
SJO
ORD
23h 05m
1 stop
ORD
SJO
9h 40m
1 stop
Depart: Wed Jan 24 2018 Return: Fri Jan 26 2018 Trip spans 3 days
Copa Airlines
Copa Airlines
GUA
ORD
31h 13m
1 stop
ORD
GUA
12h 27m
1 stop
Depart: Tue Nov 14 2017 Return: Mon Nov 20 2017 Trip spans 7 days
Volaris
Volaris
GUA
MDW
21h 25m
1 stop
MDW
GUA
18h 48m
1 stop
Depart: Wed Jan 24 2018 Return: Sun Jan 28 2018 Trip spans 5 days
Avianca
Avianca
GUA
ORD
6h 15m
1 stop
ORD
GUA
6h 20m
1 stop
Depart: Fri Nov 17 2017 Return: Sat Nov 25 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
SJO
ORD
9h 00m
1 stop
ORD
SJO
7h 35m
1 stop
Depart: Sat Nov 18 2017 Return: Sun Nov 26 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
SJO
ORD
10h 06m
1 stop
ORD
SJO
7h 35m
1 stop
Depart: Wed Feb 14 2018 Return: Wed Feb 21 2018 Trip spans 8 days
Interjet
Interjet
SJO
ORD
10h 10m
1 stop
ORD
SJO
21h 55m
1 stop
Depart: Sun Dec 10 2017 Return: Mon Feb 5 2018 Trip spans 58 days
Spirit Airlines
Spirit Airlines
SJO
ORD
9h 00m
1 stop
ORD
SJO
6h 34m
1 stop
Depart: Fri Jan 26 2018 Return: Tue Feb 6 2018 Trip spans 12 days
Interjet
Interjet
SJO
ORD
29h 15m
1 stop
ORD
SJO
11h 40m
1 stop
Depart: Tue Dec 12 2017 Return: Tue Feb 6 2018 Trip spans 57 days
Spirit Airlines
Spirit Airlines
SJO
ORD
9h 00m
1 stop
ORD
SJO
7h 35m
1 stop
Depart: Tue Dec 12 2017 Return: Sat Feb 3 2018 Trip spans 54 days
JetBlue
JetBlue
SJO
ORD
8h 21m
1 stop
ORD
SJO
7h 24m
1 stop
Depart: Thu Feb 15 2018 Return: Fri Feb 23 2018 Trip spans 9 days
Interjet
Interjet
GUA
ORD
17h 05m
1 stop
ORD
GUA
14h 05m
1 stop
Depart: Fri Nov 10 2017 Return: Sun Nov 12 2017 Trip spans 3 days
Multiple Airlines
Multiple Airlines
GUA
ORD
10h 32m
1 stop
ORD
GUA
14h 05m
1 stop
Depart: Wed Nov 29 2017 Return: Sun Dec 3 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJO
ORD
10h 06m
1 stop
ORD
SJO
6h 38m
1 stop
Depart: Wed Nov 22 2017 Return: Mon Nov 27 2017 Trip spans 6 days
Aeromexico
Aeromexico
SJO
MDW
33h 52m
2 stops
MDW
SJO
40h 59m
2 stops
Depart: Tue Nov 14 2017 Return: Mon Nov 20 2017 Trip spans 7 days
Multiple Airlines
Multiple Airlines
GUA
ORD
29h 00m
1 stop
ORD
GUA
7h 19m
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
$311
San Jose
$244
Destination

Chicago
only $244
only $404