Find Deals on 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: Tue May 9 2017 Return: Tue May 16 2017 Trip spans 8 days
JetBlue
JetBlue
SJU
ORD
8h 47m
1 stop
ORD
SJU
8h 30m
1 stop
Depart: Tue May 2 2017 Return: Mon May 8 2017 Trip spans 7 days
Major Airline
Major Airline
SJU
ORD
26h 19m
nonstop
ORD
SJU
25h 11m
nonstop
Depart: Fri Apr 21 2017 Return: Mon Apr 24 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
SJU
ORD
20h 02m
1 stop
ORD
SJU
17h 49m
1 stop
Depart: Wed Apr 26 2017 Return: Sun Apr 30 2017 Trip spans 5 days
American Airlines
American Airlines
SJU
ORD
5h 20m
nonstop
ORD
SJU
4h 34m
nonstop
Depart: Fri May 12 2017 Return: Wed May 17 2017 Trip spans 6 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 45m
nonstop
Depart: Tue Mar 14 2017 Return: Wed Mar 15 2017 Trip spans 2 days
Delta
Delta
SJU
MDW
7h 02m
1 stop
MDW
SJU
6h 51m
1 stop
Depart: Tue Apr 25 2017 Return: Sat Apr 29 2017 Trip spans 5 days
Major Airline
Major Airline
SJU
ORD
6h 56m
nonstop
ORD
SJU
28h 28m
nonstop
Depart: Wed Aug 2 2017 Return: Wed Aug 9 2017 Trip spans 8 days
American Airlines
American Airlines
SJU
ORD
5h 02m
nonstop
ORD
SJU
4h 55m
nonstop
Depart: Thu Mar 2 2017 Return: Mon Mar 13 2017 Trip spans 11 days
Spirit Airlines
Spirit Airlines
SJU
ORD
19h 18m
1 stop
ORD
SJU
17h 48m
1 stop
Depart: Wed Apr 26 2017 Return: Sun Apr 30 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
8h 20m
1 stop
MDW
SJU
6h 30m
1 stop
Depart: Tue Jul 11 2017 Return: Wed Jul 12 2017 Trip spans 2 days
JetBlue
JetBlue
SJU
ORD
6h 43m
1 stop
ORD
SJU
6h 37m
1 stop
Depart: Tue Mar 21 2017 Return: Tue Mar 28 2017 Trip spans 8 days
Major Airline
Major Airline
SJU
ORD
9h 01m
nonstop
ORD
SJU
7h 10m
nonstop
Depart: Fri Aug 18 2017 Return: Mon Aug 21 2017 Trip spans 4 days
American Airlines
American Airlines
SJU
ORD
5h 02m
nonstop
ORD
SJU
4h 55m
nonstop
Depart: Thu Apr 27 2017 Return: Mon May 1 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
9h 09m
1 stop
MDW
SJU
7h 52m
1 stop
Depart: Thu May 4 2017 Return: Mon May 8 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
7h 19m
1 stop
MDW
SJU
6h 49m
1 stop
Depart: Tue Mar 7 2017 Return: Wed Mar 15 2017 Trip spans 8 days
JetBlue
JetBlue
SJU
ORD
6h 55m
nonstop
ORD
SJU
6h 43m
nonstop
Depart: Fri Feb 24 2017 Return: Mon Feb 27 2017 Trip spans 4 days
Major Airline
Major Airline
SJU
MDW
6h 06m
nonstop
MDW
SJU
2h 06m
nonstop
Depart: Tue Jun 13 2017 Return: Tue Jul 25 2017 Trip spans 43 days
Delta
Delta
SJU
ORD
8h 20m
1 stop
ORD
SJU
8h 08m
1 stop
Depart: Sat Apr 8 2017 Return: Sat Apr 15 2017 Trip spans 8 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 45m
nonstop
Depart: Wed Jun 28 2017 Return: Thu Jul 13 2017 Trip spans 16 days
JetBlue
JetBlue
SJU
ORD
6h 43m
1 stop
ORD
SJU
6h 37m
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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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.

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Airports
Origin

San Juan
$295
Destination

Chicago
only $295
only $362
Airlines Airline reviews

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

Overall
8.5
Boarding
8.3
Crew
8.4
Comfort
8.4
Food
7.4
Entertainment
7.8