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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Book cheap flights from San Juan to Chicago

(Round-trip)
Depart: Mon Sep 11 2017 Return: Tue Sep 19 2017 Trip spans 9 days
Frontier
Frontier
SJU
ORD
18h 00m
1 stop
ORD
SJU
17h 39m
1 stop
Depart: Wed Oct 25 2017 Return: Mon Oct 30 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 35m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Wed Dec 6 2017 Return: Mon Dec 11 2017 Trip spans 6 days
American Airlines
American Airlines
SJU
ORD
5h 27m
nonstop
ORD
SJU
4h 33m
nonstop
Depart: Wed Sep 27 2017 Return: Wed Oct 11 2017 Trip spans 15 days
Delta
Delta
SJU
MDW
9h 36m
1 stop
MDW
SJU
13h 40m
2 stops
Depart: Wed Nov 1 2017 Return: Fri Nov 10 2017 Trip spans 10 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 35m
nonstop
Depart: Tue Aug 29 2017 Return: Fri Sep 29 2017 Trip spans 32 days
Major Airline
Major Airline
SJU
MDW
6h 30m
nonstop
MDW
SJU
12h 15m
nonstop
Depart: Mon Oct 2 2017 Return: Tue Oct 10 2017 Trip spans 9 days
Frontier
Frontier
SJU
ORD
18h 00m
1 stop
ORD
SJU
14h 59m
1 stop
Depart: Sat Dec 9 2017 Return: Wed Dec 13 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 28m
1 stop
ORD
SJU
6h 55m
1 stop
Depart: Mon Sep 25 2017 Return: Tue Oct 10 2017 Trip spans 16 days
Frontier
Frontier
SJU
ORD
18h 00m
1 stop
ORD
SJU
14h 59m
1 stop
Depart: Tue Sep 12 2017 Return: Mon Sep 18 2017 Trip spans 7 days
Frontier
Frontier
SJU
ORD
18h 00m
1 stop
ORD
SJU
17h 39m
1 stop
Depart: Fri Sep 8 2017 Return: Sun Sep 10 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
SJU
ORD
6h 43m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Sat Oct 14 2017 Return: Mon Oct 30 2017 Trip spans 17 days
Delta
Delta
SJU
MDW
12h 56m
2 stops
MDW
SJU
6h 24m
1 stop
Depart: Thu Jan 11 2018 Return: Tue Jan 16 2018 Trip spans 6 days
Frontier
Frontier
SJU
ORD
18h 25m
1 stop
ORD
SJU
14h 30m
1 stop
Depart: Sat Oct 14 2017 Return: Mon Oct 30 2017 Trip spans 17 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 35m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Fri Dec 22 2017 Return: Wed Jan 3 2018 Trip spans 13 days
United
United
SJU
ORD
15h 04m
1 stop
ORD
SJU
10h 59m
1 stop
Depart: Thu Aug 24 2017 Return: Sun Aug 27 2017 Trip spans 4 days
JetBlue
JetBlue
SJU
ORD
6h 43m
nonstop
ORD
SJU
6h 37m
nonstop
Depart: Wed Oct 25 2017 Return: Mon Oct 30 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
10h 45m
2 stops
MDW
SJU
6h 11m
1 stop
Depart: Thu Oct 19 2017 Return: Mon Oct 23 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 35m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Sat Dec 23 2017 Return: Fri Jan 5 2018 Trip spans 14 days
United
United
SJU
ORD
15h 04m
1 stop
ORD
SJU
12h 54m
1 stop
Depart: Thu Oct 12 2017 Return: Mon Oct 16 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
7h 15m
1 stop
MDW
SJU
6h 11m
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:

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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

San Juan
$279
Destination

Chicago
only $279
only $389
Airlines Airline reviews

56 travelers who booked a flight from San Juan to Chicago rated their chosen airlines with an average of 7.9.

Overall
8.3
Boarding
8.2
Crew
8.3
Comfort
8.1
Food
7.3
Entertainment
7.3