Find Cheap Flights from Chicago (CHI) to San Juan (SJU) from €479

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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 €217 for one-way flights and €479 for return flights, for the period specified. Prices and availability are subject to change. Additional terms apply.

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
€478
Average flight time
5 hours 50 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
United, American Airlines
Distance
Direct Flight Time
Flight Price
€479

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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
Yövy tässä ylellisessä lomakeskuksessa kohteessa San Juan. Nauti ilmaisesta Wi-Fi-yhteydestä, 3 ulkouima-altaasta ja täyden palvelun kylpylästä. Asiakkaamme ...
8.6/10 Excellent! (2,825 reviews)
"Our stay at the Caribe Hilton was great! The staff were friendly and helpful, the only 2 things that I feel need improvement are the next: The bed: The bed was extremely hard, they are just cheap Sealy mattresses. If you have back and neck issues, or issues such as Fibromyalgia… you will be waking ..."

Reviewed on 14 Jun 2026

Opens in a new windowCaribe Hilton
Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

5 out of 5
1055 Ashford Avenue San Juan
Yövy tässä ylellisessä hotellissa kohteessa San Juan. Nauti ilmaisesta Wi-Fi-yhteydestä, 4 ulkouima-altaasta ja täyden palvelun kylpylästä. Asiakkaamme kehuvat ...
9.4/10 Exceptional! (1,725 reviews)
"Good hotel with no real complaints. Cigar lounge a brilliant touch, restaurant was excellent! But the hotel rooms need upgraded if they want to drive value for both clients and stake holders. Investment in property is visibly missing!"

Reviewed on 14 Jun 2026

Opens in a new windowCondado Vanderbilt Hotel
La Concha Resort, Puerto Rico, Autograph Collection

La Concha Resort, Puerto Rico, Autograph Collection

4 out of 5
1077 Ashford Ave Condado San Juan
Yövy tässä rannalla sijaitsevassa lomakeskuksessa kohteessa San Juan. Nauti ilmaisesta Wi-Fi-yhteydestä, 3 ulkouima-altaasta ja täyden palvelun kylpylästä. Asiakkaamme ...
9.2/10 Wonderful! (2,705 reviews)
"Lovevit"

Reviewed on 14 Jun 2026

Opens in a new windowLa Concha Resort, Puerto Rico, Autograph Collection
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The Condado Plaza Hotel

The Condado Plaza Hotel

4 out of 5
999 Ashford Avenue San Juan
Yövy tässä rannalla sijaitsevassa lomakeskuksessa kohteessa San Juan. Nauti 2 ulkouima-altaasta, 2 ravintolasta ja rannasta. Asiakkaamme kehuvat majoituspaikan ...
8/10 Very Good! (2,450 reviews)
"This hotel is really old and fair maintained the rooms needed to be totally cleaned by housekeeping there were a lot of dust in the headboard of the bed Thd facilities are ok but elevator one or 2 of them broke often"

Reviewed on 14 Jun 2026

Opens in a new windowThe Condado Plaza Hotel
San Juan Marriott Resort and Stellaris Casino

San Juan Marriott Resort and Stellaris Casino

4.5 out of 5
1309 Ashford Avenue San Juan
Yövy tässä ylellisessä hotellissa kohteessa San Juan. Nauti ilmaisesta Wi-Fi-yhteydestä, 2 ulkouima-altaasta ja täyden palvelun kylpylästä. Asiakkaamme kehuvat ...
9/10 Wonderful! (1,618 reviews)
"It’s a beautiful property, but when we were at the beach with our towels/bags on the seat, they were removed and we panicked until we found our things with the beach staff, who apologized but should have known better. I paid for two rooms and expected better. Otherwise, the drinks/food were more ..."

Reviewed on 14 Jun 2026

Opens in a new windowSan Juan Marriott Resort and Stellaris Casino
AC Hotel by Marriott San Juan Condado

AC Hotel by Marriott San Juan Condado

4 out of 5
1369 Ashford Avenue San Juan
Yövy tässä liikematkustukseen soveltuvassa hotellissa kohteessa San Juan. Nauti ilmaisesta Wi-Fi-yhteydestä, kuntokeskuksesta ja pysäköinnistä (lisämaksusta). ...
8.6/10 Excellent! (1,235 reviews)
"We absolutely loved the property. So beautiful and close to the beach! We’ll always remember Our 25th wedding anniversary celebration! We’re definitely planning to come back!"

Reviewed on 13 Jun 2026

Opens in a new windowAC Hotel by Marriott San Juan Condado
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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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Flight prices above are per person all prepaid taxes and online service fees included and subject to availability