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Cheap Flights from Chicago to San Juan & Flight Information
Origin airport IATA code
CHI
Destination airport IATA code
SJU
Number of flight options
1
Average flight time
6 hours 19 mins

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
Distance
Direct Flight Time
Flight Price

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Place to stay after flight from Chicago to San Juan

The Condado Plaza Hotel

The Condado Plaza Hotel

4 out of 5
999 Ashford Avenue San Juan
Dieses Resort in Strandnähe bietet dir einen angenehmen Aufenthalt in San Juan. Freu dich auf 2 Außenpools, 2 Restaurants und am Strand. Die Gäste loben den ...
8/10 Very Good! (2,091 reviews)
Pool and hot tub where great. Ocean beach was great

Reviewed on 4 Mar 2026

Opens in a new windowThe Condado Plaza Hotel
Costa Bahia Hotel Paseo Caribe

Costa Bahia Hotel Paseo Caribe

3.5 out of 5
1 Calle San Gerónimo San Juan San Juan
Dieses Hotel für Geschäftsreisende bietet dir einen angenehmen Aufenthalt in San Juan. Freu dich auf inbegriffenes Frühstück, WLAN-Internetzugang (kostenlos) ...
7.4/10 Good! (4,008 reviews)
Only good thing was location

Reviewed on 5 Mar 2026

Opens in a new windowCosta Bahia Hotel Paseo Caribe
La Concha Resort, Puerto Rico, Autograph Collection

La Concha Resort, Puerto Rico, Autograph Collection

4 out of 5
1077 Ashford Ave Condado San Juan
Dieses Resort in Strandnähe bietet dir einen angenehmen Aufenthalt in San Juan. Freu dich auf WLAN-Internetzugang (kostenlos), 3 Außenpools und Wellnessbereich. ...
9.2/10 Wonderful! (2,489 reviews)
Hotel was nice and clean. Staff were always friendly. They had amazing cookies

Reviewed on 4 Mar 2026

Opens in a new windowLa Concha Resort, Puerto Rico, Autograph Collection
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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 im luxuriösen Stil bietet dir einen angenehmen Aufenthalt in San Juan. Freu dich auf WLAN-Internetzugang (kostenlos), 2 Außenpools und Wellnessbereich. ...
9/10 Wonderful! (1,542 reviews)
Overall, our experience was pleasant. However, the additional resort charges of $70+ per night felt deceptive when we discovered them at check-in. It became a noticeable topic of conversation among several guests waiting in line. Had these fees been clearly disclosed upfront, I most likely still ...

Reviewed on 4 Mar 2026

Opens in a new windowSan Juan Marriott Resort and Stellaris Casino
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. ...
8.6/10 Excellent! (2,588 reviews)
This hotel is great to enjoy SJU and vacations! Pools are great and the view is amazing!

Reviewed on 4 Mar 2026

Opens in a new windowCaribe Hilton
Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

5 out of 5
1055 Ashford Avenue San Juan
Dieses Hotel im luxuriösen Stil bietet dir einen angenehmen Aufenthalt in San Juan. Freu dich auf WLAN-Internetzugang (kostenlos), 4 Außenpools und Wellnessbereich. ...
9.4/10 Exceptional! (1,698 reviews)
Absolutely gorgeous hotel with outstanding service! Close to everything, excellent restaurants right in the hotel. Truly a 5 star resort!

Reviewed on 3 Mar 2026

Opens in a new windowCondado Vanderbilt Hotel
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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.

^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.