Find Cheap Flights from Chicago 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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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago to Central America

(Round-trip)
Depart: Wed Sep 6 2017 Return: Sun Sep 10 2017 Trip spans 5 days
Interjet
Interjet
ORD
GUA
26h 10m
1 stop
GUA
ORD
19h 30m
1 stop
Depart: Sat May 27 2017 Return: Sun May 28 2017 Trip spans 2 days
American Airlines
American Airlines
ORD
SJO
18h 04m
1 stop
SJO
ORD
8h 21m
1 stop
Depart: Sun Jun 11 2017 Return: Mon Jun 12 2017 Trip spans 2 days
Major Airline
Major Airline
ORD
SAP
21h 24m
1 stop
SAP
ORD
18h 45m
1 stop
Depart: Wed Jun 7 2017 Return: Wed Jun 14 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
PTY
17h 43m
1 stop
PTY
ORD
8h 54m
1 stop
Depart: Wed Nov 1 2017 Return: Sat Nov 4 2017 Trip spans 4 days
Aeromexico
Aeromexico
ORD
SJO
18h 10m
1 stop
SJO
ORD
10h 05m
1 stop
Depart: Sat May 27 2017 Return: Sun Jun 4 2017 Trip spans 9 days
United
United
ORD
SJO
7h 30m
1 stop
SJO
ORD
8h 45m
1 stop
Depart: Thu Jul 27 2017 Return: Tue Aug 1 2017 Trip spans 6 days
Copa Airlines
Copa Airlines
ORD
BZE
23h 51m
1 stop
BZE
ORD
9h 14m
1 stop
Depart: Sun Oct 8 2017 Return: Sun Oct 15 2017 Trip spans 8 days
Avianca
Avianca
ORD
SJO
6h 55m
1 stop
SJO
ORD
6h 53m
1 stop
Depart: Tue Jun 13 2017 Return: Thu Jun 15 2017 Trip spans 3 days
Delta
Delta
MDW
SJO
11h 57m
2 stops
SJO
MDW
15h 02m
1 stop
Depart: Sun Oct 8 2017 Return: Sun Oct 15 2017 Trip spans 8 days
Volaris
Volaris
MDW
SJO
18h 20m
1 stop
SJO
MDW
21h 53m
1 stop
Depart: Tue Jun 13 2017 Return: Mon Jun 19 2017 Trip spans 7 days
Hahn Air Systems
Hahn Air Systems
MDW
SJO
18h 18m
1 stop
SJO
MDW
22h 11m
1 stop
Depart: Tue Oct 17 2017 Return: Wed Nov 22 2017 Trip spans 37 days
Interjet
Interjet
ORD
GUA
22h 15m
1 stop
GUA
ORD
16h 55m
1 stop
Depart: Fri Jun 2 2017 Return: Tue Jun 6 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
SJO
20h 40m
1 stop
SJO
ORD
30h 42m
1 stop
Depart: Wed Jul 12 2017 Return: Mon Jul 17 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
PTY
17h 39m
1 stop
PTY
ORD
8h 49m
1 stop
Depart: Tue Jul 4 2017 Return: Tue Jul 11 2017 Trip spans 8 days
Aeromexico
Aeromexico
ORD
SJO
28h 50m
1 stop
SJO
ORD
16h 20m
1 stop
Depart: Wed Aug 30 2017 Return: Sun Sep 3 2017 Trip spans 5 days
Interjet
Interjet
ORD
GUA
9h 55m
1 stop
GUA
ORD
19h 30m
1 stop
Depart: Fri Nov 3 2017 Return: Wed Nov 15 2017 Trip spans 13 days
Major Airline
Major Airline
ORD
GUA
12h 30m
1 stop
GUA
ORD
15h 06m
1 stop
Depart: Tue Jun 13 2017 Return: Wed Jun 28 2017 Trip spans 16 days
Aeromexico
Aeromexico
ORD
SJO
11h 30m
1 stop
SJO
ORD
15h 03m
2 stops
Depart: Sat Sep 2 2017 Return: Mon Sep 4 2017 Trip spans 3 days
Interjet
Interjet
ORD
GUA
26h 10m
1 stop
GUA
ORD
15h 45m
1 stop
Depart: Wed Sep 20 2017 Return: Mon Sep 25 2017 Trip spans 6 days
Delta
Delta
MDW
SJO
13h 20m
1 stop
SJO
MDW
14h 47m
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.

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

Chicago
only $278
only $402
Destination

Guatemala City
$278
Panama City
$334
San Pedro Sula
$322
Belize City
$378
San Jose
$291