Find Cheap Flights from Chicago (CHI) to San Juan (SJU) from CHF 321

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Selected flight deals from Chicago to San Juan

The lowest prices found within the past 7 days from Chicago to San Juan were for one-way flights and CHF 321 for return flights, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, 26 Sep - Sun, 28 Sep
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
CHF 321 Return, found 6 days ago
CHF 321
Return
found 6 days ago
Select JetBlue Airways flight, departing Fri, 26 Sep from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, 28 Sep, priced at CHF 321 found 6 days ago
Fri, 26 Sep - Sun, 28 Sep
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
CHF 326 Return, found 6 days ago
CHF 326
Return
found 6 days ago
Select JetBlue Airways flight, departing Fri, 26 Sep from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, 28 Sep, priced at CHF 326 found 6 days ago
Fri, 26 Sep - Sun, 28 Sep
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
CHF 329 Return, found 6 days ago
CHF 329
Return
found 6 days ago
Select JetBlue Airways flight, departing Fri, 26 Sep from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, 28 Sep, priced at CHF 329 found 6 days ago
Fri, 26 Sep - Sun, 28 Sep
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
CHF 334 Return, found 6 days ago
CHF 334
Return
found 6 days ago
Select JetBlue Airways flight, departing Fri, 26 Sep from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, 28 Sep, priced at CHF 334 found 6 days ago
Fri, 26 Sep - Sun, 28 Sep
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
CHF 355 Return, found 6 days ago
CHF 355
Return
found 6 days ago
Select JetBlue Airways flight, departing Fri, 26 Sep from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, 28 Sep, priced at CHF 355 found 6 days ago
Fri, 26 Sep - Sun, 28 Sep
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
CHF 356 Return, found 6 days ago
CHF 356
Return
found 6 days ago
Select JetBlue Airways flight, departing Fri, 26 Sep from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, 28 Sep, priced at CHF 356 found 6 days ago
Fri, 26 Sep - Sun, 28 Sep
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
CHF 364 Return, found 6 days ago
CHF 364
Return
found 6 days ago
Select JetBlue Airways flight, departing Fri, 26 Sep from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, 28 Sep, priced at CHF 364 found 6 days ago
Fri, 26 Sep - Sun, 28 Sep
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
CHF 365 Return, found 6 days ago
CHF 365
Return
found 6 days ago
Select JetBlue Airways flight, departing Fri, 26 Sep from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, 28 Sep, priced at CHF 365 found 6 days ago
Fri, 26 Sep - Sun, 28 Sep
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
CHF 369 Return, found 6 days ago
CHF 369
Return
found 6 days ago
Select JetBlue Airways flight, departing Fri, 26 Sep from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, 28 Sep, priced at CHF 369 found 6 days ago
Fri, 26 Sep - Sun, 28 Sep
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
CHF 377 Return, found 6 days ago
CHF 377
Return
found 6 days ago
Select JetBlue Airways flight, departing Fri, 26 Sep from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, 28 Sep, priced at CHF 377 found 6 days ago
Cheap Flights from Chicago to San Juan & Flight Information
Origin airport IATA code
ORD
Destination airport IATA code
SJU
Number of flight options
1
Return price
CHF 321
Average flight time
5 hours 47 mins

Best Day to Book Flight from Chicago to San Juan

San Juan Flight Information

Traveling From
Chicago
Origin Airport IATA Code
CHI
Traveling To
San Juan
Destination Airport IATA Code
SJU
Number of Airlines Serving
Available Airlines
JetBlue Airways
Distance
Direct Flight Time
Flight Price
CHF 321

Need a car after flight from Chicago to San Juan

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Place to stay after flight from Chicago to San Juan

Caribe Hilton

Caribe Hilton

4.5 out of 5
1 San Geronimo Street, San Juan
Dieses Resort in Strandnähe bietet dir einen angenehmen Aufenthalt in San Juan. Freu dich auf WLAN-Internetzugang (kostenlos), 3 Außenpools und Wellnessbereich. ...
8.4/10 Very Good! (1,858 reviews)
"Place was nice , clean and staff were very friendly."

Reviewed on 11 Jun 2025

Caribe Hilton
San Juan Marriott Resort and Stellaris Casino

San Juan Marriott Resort and Stellaris Casino

4.5 out of 5
1309 Ashford Avenue, San Juan
Dieses Hotel mit 4,5 Sternen im luxuriösen Stil bietet dir einen angenehmen Aufenthalt in San Juan. Freu dich auf WLAN-Internetzugang (kostenlos), 2 Außenpools ...
9/10 Wonderful! (1,232 reviews)
"Great beach access with pool room was nice and casino for the wait"

Reviewed on 12 Jun 2025

San Juan Marriott Resort and Stellaris Casino
La Concha Renaissance San Juan Resort

La Concha Renaissance San Juan Resort

4 out of 5
1077 Ashford Ave Condado, San Juan
Dieses Resort mit 4 Sternen in Strandnähe bietet dir einen angenehmen Aufenthalt in San Juan. Freu dich auf WLAN-Internetzugang (kostenlos), 3 Außenpools und ...
8.8/10 Excellent! (1,887 reviews)
"Perfect place to stay. Very clean"

Reviewed on 13 Jun 2025

La Concha Renaissance San Juan Resort
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Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

5 out of 5
1055 Ashford Avenue, San Juan
Dieses Hotel mit 5 Sternen im luxuriösen Stil bietet dir einen angenehmen Aufenthalt in San Juan. Freu dich auf WLAN-Internetzugang (kostenlos), 4 Außenpools ...
9/10 Wonderful! (1,507 reviews)
"Amazing property!"

Reviewed on 12 Jun 2025

Condado Vanderbilt Hotel
Hilton Garden Inn San Juan Condado

Hilton Garden Inn San Juan Condado

4 out of 5
886 Ashford Ave, San Juan
Dieses Hotel mit 4 Sternen mit Wellnessangebot bietet dir einen angenehmen Aufenthalt in San Juan. Freu dich auf WLAN-Internetzugang (kostenlos), Wellnessbereich ...
8.8/10 Excellent! (862 reviews)
"The property is good in appearance however I sent a request via expedia and till now they never responded. I also reached out to the hotel directly way ahead of the trip and they did not respond. I then called them and even though the front desk picked, i was transferred to concierge that did not ..."

Reviewed on 10 Jun 2025

Hilton Garden Inn San Juan Condado
El Colonial - Adults Only

El Colonial - Adults Only

3.5 out of 5
312 C. de San Francisco, San Juan, San Juan
Dieses Hotel mit 3,5 Sternen bietet dir einen angenehmen Aufenthalt in San Juan. Freu dich auf WLAN-Internetzugang (kostenlos), eine rund um die Uhr besetzte ...
9.4/10 Exceptional! (1,182 reviews)
"Everything perfectly on point and the service was great"

Reviewed on 10 Jun 2025

El Colonial - Adults Only
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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.

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^Savings based on all holiday package bookings with Flight + Hotel made on ebookers.ie from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.