Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Cheap flights from Chicago (CHI) to San Juan (SJU)

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Lowest round trip fares by airline from Chicago and San Juan

Cheapest prices ($81 One Way, $172 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sun, Jul 4
ORD
Chicago
SJU
San Juan
$81
Spirit Airlines
Tue, Sep 28
ORD
Chicago
SJU
San Juan
$85
United
Wed, Sep 29
ORD
Chicago
SJU
San Juan
$89
Delta
Tue, Sep 28
ORD
Chicago
SJU
San Juan
$89
Frontier Airlines
Wed, Dec 1
ORD
Chicago
SJU
San Juan
$90
Frontier Airlines
Tue, Sep 14 - Tue, Sep 14
ORD
Chicago
SJU
San Juan
$172
Delta
Tue, Sep 14 - Tue, Sep 21
ORD
Chicago
SJU
San Juan
$173
United
Tue, Sep 14 - Tue, Sep 21
ORD
Chicago
SJU
San Juan
$175
United
Tue, Oct 26 - Tue, Oct 26
ORD
Chicago
SJU
San Juan
$178
United
Tue, Sep 21 - Tue, Sep 28
ORD
Chicago
SJU
San Juan
$178
Frontier Airlines

Great Deals On Cheap Hotels in San Juan

Casa del Caribe Inn

Casa del Caribe Inn

2 out of 5
57 Caribe St., Condado, San Juan
The price is $80 per night from Jun 27 to Jun 27
Located in Condado, this inn is within a 10-minute walk of Atlantic Beach and Casino del Mar at La Concha Resort. Condado Beach and Escambron Beach are also ...
3.4/5Good! (16 reviews)
"Location was the best part. Roaches and no ameneties. Unfriendly staff."

Reviewed on Jun 13, 2019

Casa del Caribe Inn
CIQALA Luxury Suites

CIQALA Luxury Suites

4 out of 5
752 Manuel Fernandez Juncos Ave, San Juan
The price is $255 per night from Jul 14 to Jul 14
Located in Miramar, this aparthotel is within a 15-minute walk of Conservatory of Music of Puerto Rico and Puerto Rico Convention Center. Condado Beach and Pan ...
4.1/5Very Good! (36 reviews)
"Great deal very nice travel and out the country for very low was a great time"

Reviewed on Oct 27, 2020

CIQALA Luxury Suites
The Condado Plaza Hilton

The Condado Plaza Hilton

4.5 out of 5
999 Ashford Avenue, San Juan
The price is $324 per night from Jul 5 to Jul 5
Located in Condado, this beachfront resort is in the city center and within a 15-minute walk of Parque La Ventana al Mar, Condado Beach, and Luis Muñoz Rivera ...
4.1/5Very Good! (39 reviews)
"The hotel is nice and clean. Was very close to restaurants and right on its own beach. Only dislike is that everything closed early or wasnt open at all. Beach and pool closed and 6pm. The café on the property wasnt open on certain days."

Reviewed on Apr 24, 2021

The Condado Plaza Hilton
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Flights Review

Fly From Chicago to San Juan

Origin Chicago
Destination San Juan
Number of Daily Flights 11
Earliest Flight Departure Date Jun 21
Latest Flight Departure Date Jun 21
Popular Airlines Frontier Airlines

Chicago to San Juan

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.