Find Cheap Flights from San Juan 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 San Juan to Chicago

(Round-trip)
Depart: Thu Aug 17 2017 Return: Fri Aug 18 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 16m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Tue Oct 3 2017 Return: Sat Oct 7 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
17h 02m
2 stops
MDW
SJU
21h 13m
2 stops
Depart: Tue Jul 11 2017 Return: Mon Jul 31 2017 Trip spans 21 days
Major Airline
Major Airline
SJU
ORD
11h 03m
nonstop
ORD
SJU
11h 18m
nonstop
Depart: Sat Jun 17 2017 Return: Fri Jun 23 2017 Trip spans 7 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 45m
nonstop
Depart: Tue Jul 11 2017 Return: Tue Jul 25 2017 Trip spans 15 days
Southwest
Southwest
SJU
MDW
7h 30m
1 stop
MDW
SJU
7h 30m
2 stops
Depart: Thu Nov 16 2017 Return: Mon Nov 27 2017 Trip spans 12 days
American Airlines
American Airlines
SJU
ORD
5h 02m
nonstop
ORD
SJU
4h 55m
nonstop
Depart: Tue Oct 3 2017 Return: Wed Oct 11 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
SJU
ORD
6h 44m
1 stop
ORD
SJU
18h 45m
1 stop
Depart: Thu Aug 31 2017 Return: Tue Sep 5 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 16m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Wed Sep 20 2017 Return: Mon Sep 25 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
10h 37m
2 stops
MDW
SJU
6h 22m
1 stop
Depart: Thu Sep 28 2017 Return: Sun Oct 1 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 32m
1 stop
ORD
SJU
6h 53m
1 stop
Depart: Thu Oct 12 2017 Return: Mon Oct 16 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
8h 17m
1 stop
MDW
SJU
7h 52m
1 stop
Depart: Fri Sep 29 2017 Return: Mon Oct 2 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
SJU
ORD
6h 44m
1 stop
ORD
SJU
8h 11m
1 stop
Depart: Fri Jul 14 2017 Return: Wed Jul 26 2017 Trip spans 13 days
Major Airline
Major Airline
SJU
ORD
12h 42m
nonstop
ORD
SJU
8h 41m
nonstop
Depart: Sat Jun 24 2017 Return: Wed Jul 5 2017 Trip spans 12 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 45m
nonstop
Depart: Thu Oct 5 2017 Return: Tue Oct 10 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 32m
1 stop
ORD
SJU
6h 53m
1 stop
Depart: Wed Aug 30 2017 Return: Wed Sep 6 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
8h 17m
1 stop
MDW
SJU
13h 53m
2 stops
Depart: Sun Jul 23 2017 Return: Mon Jul 31 2017 Trip spans 9 days
Major Airline
Major Airline
SJU
ORD
12h 42m
nonstop
ORD
SJU
11h 18m
nonstop
Depart: Thu Oct 12 2017 Return: Mon Oct 16 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJU
ORD
6h 44m
1 stop
ORD
SJU
8h 11m
1 stop
Depart: Sat May 27 2017 Return: Fri Jun 16 2017 Trip spans 21 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 45m
nonstop
Depart: Thu Jun 8 2017 Return: Thu Jun 22 2017 Trip spans 15 days
Southwest
Southwest
SJU
MDW
6h 50m
1 stop
MDW
SJU
6h 45m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

San Juan
$300
Destination

Chicago
only $300
only $379
Airlines Airline reviews

41 travelers who booked a flight from San Juan to Chicago rated their chosen airlines with an average of 8.1.

Overall
8.4
Boarding
8.2
Crew
8.3
Comfort
8.2
Food
7.2
Entertainment
7.7