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Explore our most popular vacation packages from Chicago - AnywhereFromcmp-location-selector-label-collapsed-menssage cmp-location-selector-label-description-origin Tocmp-location-selector-label-collapsed-menssage cmp-location-selector-label-description-destination ClearDoneBudgetNumber of nightsNumber of nightsAny number of nightsCLEARDONEAdvancedNumber of nightsNumber of nightsNumbers of starsClearDoneCLEARSORT: Popularcmp-carousel-container-explain1/166days(s)FromChicagoPackages toCancun10/10/2024 October 10, 2024-10/16/2024 October 16, 2024Flight+HotelFromUSDUSD767* cmp-price-disclaimerSeen:a day ago Round Trip2/166days(s)FromChicagoPackages toCancun10/10/2024 October 10, 2024-10/16/2024 October 16, 2024Flight+HotelFromUSDUSD783* cmp-price-disclaimerSeen:a day ago Round Trip3/167days(s)FromChicagoPackages toCancun08/24/2024 August 24, 2024-08/31/2024 August 31, 2024Flight+HotelFromUSDUSD684* cmp-price-disclaimerSeen:a day ago Round Trip4/167days(s)FromChicagoPackages toCancun08/24/2024 August 24, 2024-08/31/2024 August 31, 2024Flight+HotelFromUSDUSD1,215* cmp-price-disclaimerSeen:a day ago Round Trip5/167days(s)FromChicagoPackages toCancun08/24/2024 August 24, 2024-08/31/2024 August 31, 2024Flight+HotelFromUSDUSD1,546* cmp-price-disclaimerSeen:a day ago Round Trip6/167days(s)FromChicagoPackages toCancun08/24/2024 August 24, 2024-08/31/2024 August 31, 2024Flight+HotelFromUSDUSD1,817* cmp-price-disclaimerSeen:a day ago Round Trip7/165days(s)FromChicagoPackages toCancun10/10/2024 October 10, 2024-10/15/2024 October 15, 2024Flight+HotelFromUSDUSD1,064* cmp-price-disclaimerSeen:a day ago Round Trip8/162days(s)FromChicagoPackages toGuadalajara10/04/2024 October 4, 2024-10/06/2024 October 6, 2024Flight+HotelFromUSDUSD377* cmp-price-disclaimerSeen:a day ago Round Trip9/162days(s)FromChicagoPackages toGuadalajara10/04/2024 October 4, 2024-10/06/2024 October 6, 2024Flight+HotelFromUSDUSD385* cmp-price-disclaimerSeen:a day ago Round Trip10/162days(s)FromChicagoPackages toGuadalajara10/04/2024 October 4, 2024-10/06/2024 October 6, 2024Flight+HotelFromUSDUSD401* cmp-price-disclaimerSeen:a day ago Round Trip11/162days(s)FromChicagoPackages toGuadalajara10/04/2024 October 4, 2024-10/06/2024 October 6, 2024Flight+HotelFromUSDUSD443* cmp-price-disclaimerSeen:a day ago Round Trip12/162days(s)FromChicagoPackages toGuadalajara10/04/2024 October 4, 2024-10/06/2024 October 6, 2024Flight+HotelFromUSDUSD618* cmp-price-disclaimerSeen:a day ago Round Trip13/163days(s)FromChicagoPackages toLeon02/27/2025 February 27, 2025-03/02/2025 March 2, 2025Flight+HotelFromUSDUSD424* cmp-price-disclaimerSeen:4 hours ago Round Trip14/163days(s)FromChicagoPackages toLeon02/27/2025 February 27, 2025-03/02/2025 March 2, 2025Flight+HotelFromUSDUSD497* cmp-price-disclaimerSeen:4 hours ago Round Trip15/163days(s)FromChicagoPackages toLeon02/27/2025 February 27, 2025-03/02/2025 March 2, 2025Flight+HotelFromUSDUSD582* cmp-price-disclaimerSeen:4 hours ago Round Trip16/169days(s)FromChicagoPackages toGuadalajara07/30/2024 July 30, 2024-08/08/2024 August 8, 2024Flight+HotelFromUSDUSD958* cmp-price-disclaimerSeen:a day ago Round Tripcmp-carousel-slide 1 cmp-carousel-of 4*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply.