Find Deals on 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: Tue Mar 28 2017 Return: Tue Apr 4 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
SJO
ORD
9h 17m
1 stop
ORD
SJO
7h 03m
1 stop
Depart: Wed May 17 2017 Return: Wed May 24 2017 Trip spans 8 days
Interjet
Interjet
GUA
ORD
27h 40m
1 stop
ORD
GUA
26h 05m
1 stop
Depart: Tue May 9 2017 Return: Tue May 16 2017 Trip spans 8 days
Copa Airlines
Copa Airlines
SJO
ORD
10h 29m
1 stop
ORD
SJO
8h 46m
1 stop
Depart: Thu Apr 13 2017 Return: Wed Apr 19 2017 Trip spans 7 days
Delta
Delta
SJO
MDW
8h 25m
1 stop
MDW
SJO
7h 02m
1 stop
Depart: Sat Mar 25 2017 Return: Sat Apr 1 2017 Trip spans 8 days
United
United
SJO
ORD
9h 47m
1 stop
ORD
SJO
5h 15m
nonstop
Depart: Thu Feb 23 2017 Return: Tue Feb 28 2017 Trip spans 6 days
American Airlines
American Airlines
SJO
ORD
17h 07m
2 stops
ORD
SJO
9h 21m
1 stop
Depart: Wed Apr 26 2017 Return: Mon May 15 2017 Trip spans 20 days
Aeromexico
Aeromexico
MGA
ORD
27h 30m
1 stop
ORD
MGA
27h 26m
1 stop
Depart: Wed May 24 2017 Return: Mon May 29 2017 Trip spans 6 days
Major Airline
Major Airline
BZE
ORD
2h 22m
nonstop
ORD
BZE
4h 22m
nonstop
Depart: Mon Mar 6 2017 Return: Sat Mar 11 2017 Trip spans 6 days
Avianca
Avianca
PTY
ORD
15h 30m
2 stops
ORD
PTY
17h 11m
2 stops
Depart: Thu Mar 2 2017 Return: Mon Mar 6 2017 Trip spans 5 days
Volaris
Volaris
SJO
MDW
22h 02m
1 stop
MDW
SJO
18h 15m
1 stop
Depart: Tue Apr 18 2017 Return: Tue May 16 2017 Trip spans 29 days
Spirit Airlines
Spirit Airlines
SJO
ORD
9h 18m
1 stop
ORD
SJO
8h 00m
1 stop
Depart: Thu Apr 27 2017 Return: Mon May 1 2017 Trip spans 5 days
Delta
Delta
SJO
MDW
9h 18m
1 stop
MDW
SJO
8h 25m
1 stop
Depart: Sun Mar 12 2017 Return: Mon Mar 27 2017 Trip spans 15 days
Interjet
Interjet
GUA
ORD
19h 45m
1 stop
ORD
GUA
26h 05m
1 stop
Depart: Tue Aug 1 2017 Return: Thu Aug 10 2017 Trip spans 10 days
American Airlines
American Airlines
SJO
ORD
11h 21m
2 stops
ORD
SJO
10h 17m
1 stop
Depart: Fri May 19 2017 Return: Tue May 23 2017 Trip spans 5 days
Delta
Delta
SJO
ORD
9h 34m
1 stop
ORD
SJO
6h 46m
1 stop
Depart: Mon Jun 19 2017 Return: Mon Jun 26 2017 Trip spans 8 days
Copa Airlines
Copa Airlines
SJO
ORD
28h 24m
1 stop
ORD
SJO
22h 21m
1 stop
Depart: Thu Aug 24 2017 Return: Sat Sep 23 2017 Trip spans 31 days
Aeromexico
Aeromexico
GUA
ORD
17h 55m
1 stop
ORD
GUA
8h 28m
1 stop
Depart: Mon Mar 6 2017 Return: Mon Mar 13 2017 Trip spans 7 days
United
United
BZE
ORD
17h 09m
1 stop
ORD
BZE
9h 18m
1 stop
Depart: Fri May 5 2017 Return: Sat May 13 2017 Trip spans 9 days
Interjet
Interjet
GUA
ORD
15h 40m
1 stop
ORD
GUA
14h 25m
1 stop
Depart: Tue Mar 14 2017 Return: Sun Mar 19 2017 Trip spans 6 days
Delta
Delta
SJO
MDW
27h 14m
1 stop
MDW
SJO
14h 02m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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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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
$298
Panama City
$413
Managua
$369
Belize City
$377
San Jose
$263
Destination

Chicago
only $263
only $316
Airlines Airline reviews

2 travelers who booked a flight from San Jose to Chicago rated their chosen airlines with an average of 9.8.

Overall
10.0
Boarding
10.0
Crew
10.0
Comfort
9.0
Food
10.0
Entertainment
10.0