Skip to main content

Vacations from Chicago to Cancun

See other vacation package offers

cmp-carousel-container-explain
5night(s)
The Beachfront by the Fives Hotels
-
Chicago (ORD) To Cancun (CUN)
Flight+Hotel
from
$788 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:23 hours ago
5night(s)
Dreams Tulum Resort and Spa
-
Chicago (ORD) To Cancun (CUN)
Flight+Hotel
from
$962 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:23 hours ago
5night(s)
The Fives Beach Hotel and Residences
-
Chicago (ORD) To Cancun (CUN)
Flight+Hotel
from
$985 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:23 hours ago
5night(s)
Hideaway at Royalton Riviera Cancun
-
Chicago (ORD) To Cancun (CUN)
Flight+Hotel
from
$993 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:23 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 Cancun

$

  • 3 night stay

    Kempinski Hotel Cancun

    gradegradegradegradegradegradegradegradegradegrade
    ORD - CUN
    3/29/2025 - 4/01/2025
    from
    $650*
    per person based on 2-person occupancy
    Updated:4hoursago

  • 5 night stay

    Izla Beach Front Hotel

    gradegradegradegradegradegradegradegradegradegrade
    ORD - CUN
    6/01/2025 - 6/06/2025
    from
    $828*
    per person based on 2-person occupancy
    Updated:9hoursago

  • 3 night stay

    Barcelo Maya Riviera

    gradegradegradegradegradegradegradegradegradegrade
    ORD - CUN
    5/03/2025 - 5/06/2025
    from
    $681*
    per person based on 2-person occupancy
    Updated:4hoursago

  • 3 night stay

    The Hilton Playa Del Carmen Resort

    gradegradegradegradegradegradegradegradegradegrade
    ORD - CUN
    5/03/2025 - 5/06/2025
    from
    $695*
    per person based on 2-person occupancy
    Updated:4hoursago

  • 3 night stay

    Breathless Cancun Soul

    gradegradegradegradegradegradegradegradegradegrade
    ORD - CUN
    5/03/2025 - 5/06/2025
    from
    $789*
    per person based on 2-person occupancy
    Updated:4hoursago

    • *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 Cancun

    Weather in Cancun

    Sunday sky is clear
    85°F 3/09/2025
    Monday moderate rain
    82°F 3/10/2025
    Tuesday scattered clouds
    81°F 3/11/2025
    Wednesday scattered clouds
    80°F 3/12/2025
    Thursday broken clouds
    82°F 3/13/2025
    Friday sky is clear
    85°F 3/14/2025
    Saturday sky is clear
    84°F 3/15/2025
    Powered by: OpenWeatherMap.org

    You may also like...