Skip to main content

Vacations from Chicago to San Juan

See other vacation package offers

cmp-carousel-container-explain
5night(s)
Boqueron Beach Resort
-
Chicago (ORD) To San Juan (SJU)
Flight+Hotel
from
$830 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:4 hours ago
5night(s)
Ponce Plaza Hotel Casino
-
Chicago (ORD) To San Juan (SJU)
Flight+Hotel
from
$958 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:4 hours ago
5night(s)
Hotel Puerto Valdes
-
Chicago (ORD) To San Juan (SJU)
Flight+Hotel
from
$980 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:8 hours ago
5night(s)
Abitta Hotel, Ascend Hotel Collection
-
Chicago (ORD) To San Juan (SJU)
Flight+Hotel
from
$988 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:4 hours ago
cmp-carousel-slide 1 cmp-carousel-of 8
*Average total price per person based on round trip flights in the Main Cabin and double occupancy hotel stays. Prices displayed have been collected within the last 24 hrs and may no longer be available at time of booking. Modifying this information may result in a different price. To find the most updated price, please visit aavacations.com.
cmp-clean-button-action-description-origin
cmp-clean-button-action-description-destination
Disclaimer
Advanced search
Bag and optional fees
Changes to checked bag fees and allowances

Choose 2 or more:

Please check if you want to include it in the search.

Enter to select travel class and passengers


Changes to checked bag fees and allowances Opens external site in a new window

Discover our best deals from Chicago to San Juan

$

  • 4 night stay

    Hyatt Residence Club Dorado, Hacienda Del Mar

    gradegradegradegradegradegradegradegradegradegrade
    ORD - SJU
    4/21/2025 - 4/25/2025
    from
    $742*
    per person based on 2-person occupancy
    Updated:11hoursago

  • 4 night stay

    VERDE by DW

    gradegradegradegradegradegradegradegradegradegrade
    ORD - SJU
    4/21/2025 - 4/25/2025
    from
    $719*
    per person based on 2-person occupancy
    Updated:11hoursago

  • 4 night stay

    Abitta Hotel, Ascend Hotel Collection

    gradegradegradegradegradegradegradegradegradegrade
    ORD - SJU
    4/21/2025 - 4/25/2025
    from
    $571*
    per person based on 2-person occupancy
    Updated:11hoursago

  • 4 night stay

    Mare 1562

    gradegradegradegradegradegradegradegradegradegrade
    ORD - SJU
    4/21/2025 - 4/25/2025
    from
    $588*
    per person based on 2-person occupancy
    Updated:11hoursago

  • 4 night stay

    Hotel Puerto Valdes

    gradegradegradegradegradegradegradegradegradegrade
    ORD - SJU
    4/21/2025 - 4/25/2025
    from
    $590*
    per person based on 2-person occupancy
    Updated:11hoursago

    • *Average total price per person based on round trip flights in the Main Cabin and double occupancy hotel stays. Prices displayed have been collected within the last 24 hrs and may no longer be available at time of booking. Modifying this information may result in a different price. To find the most updated price, please visit aavacations.com.

    Vacations from Chicago to San Juan

    Weather in San Juan

    Monday light rain
    83°F 3/10/2025
    Tuesday scattered clouds
    80°F 3/11/2025
    Wednesday sky is clear
    83°F 3/12/2025
    Thursday sky is clear
    81°F 3/13/2025
    Friday moderate rain
    82°F 3/14/2025
    Saturday light rain
    80°F 3/15/2025
    Sunday light rain
    80°F 3/16/2025
    Powered by: OpenWeatherMap.org

    You may also like...