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  • Nonstop Vacation Deal

    Dreams Puerto Morelos Resort & Spa
    4 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    Apr 5, 2026
    3 Nights Includes Taxes + Fees
    $827 per person
  • Nonstop Vacation Deal
    TripAdvisor Traveler Rating
    TripAdvisor Reviews

    Dreams Tulum Resort & Spa - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    Apr 5, 2026
    3 Nights Includes Taxes + Fees
    $895 per person
  • Nonstop Vacation Deal
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Includes savings up to 72%
    Limited time steal of a deal

    Hyatt Zilara Riviera Maya - All Inclusive - Adults Only
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    2026: Apr 12, Apr 14, Apr 27
    3 Nights Includes Taxes + Fees
    $849 per person
  • Nonstop Vacation Deal

    Dreams Cap Cana - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Dominican Republic, Punta Cana
    Best Priced Departure Dates
    Apr 9, 2026
    3 Nights Includes Taxes + Fees
    $1,064 per person

  • Dreams Puerto Morelos Resort & Spa
    4 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    Apr 20, 2026
    3 Nights Includes Taxes + Fees
    $660 per person
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews

    Dreams Tulum Resort & Spa - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    Apr 14, 2026
    3 Nights Includes Taxes + Fees
    $772 per person
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Includes savings up to 72%
    Limited time steal of a deal

    Hyatt Zilara Riviera Maya - All Inclusive - Adults Only
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    Apr 14, 2026
    3 Nights Includes Taxes + Fees
    $787 per person

  • Dreams Cap Cana - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Dominican Republic, Punta Cana
    Best Priced Departure Dates
    Apr 20, 2026
    3 Nights Includes Taxes + Fees
    $951 per person
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Includes savings up to 61%
    Limited time steal of a deal

    Sunscape Puerto Vallarta Resort & Spa - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Puerto Vallarta - Riviera Nayarit
    Best Priced Departure Dates
    2026: Apr 12 - Apr 14
    3 Nights Includes Taxes + Fees
    $817 per person
Not seeing deals? Modify your travel preferences, change your destination, or select new dates.

Chicago vacations don't have to be complicated or expensive. With Apple Vacations, you can "Start Your Story" in international and U.S. sun-soaked destinations while keeping your budget happy.

Whether you're celebrating a festive occasion with your partner, taking the kids on a fun-filled adventure, or enjoying a multi-generational family reunion, affordable packages make it easy to get the best flight deals from Chicago while enjoying many other amenities. Pair our flight deals from Chicago with our incredible resorts, and you have the perfect recipe for an affordable, no-stress vacation. This is "Where Your Story Starts."

Vacation Deals From Chicago FAQ

What destinations have the cheapest vacation deals from Chicago?

Our Chicago vacation packages to Las Vegas, California, and Florida are typically the most budget-friendly options and offer a range of experiences, from colorful nightlife to tranquil beaches. Booking vacation packages maximizes savings by bundling flights, accommodations, meals, drinks, and entertainment into one price. You can also travel during off-peak months in the fall or winter to save even more.

How far in advance should I book from Chicago for the best price?

To get the best flight deals from Chicago, schedule your trip around one to six months in advance. This timeframe allows you to take advantage of last minute lower fares before hotels sell out closer to departure. By planning in advance and staying flexible with your flying dates, you can plan a memorable trip at a low price.

Are last minute vacation deals from Chicago worth it?

Yes! Last minute vacation deals from Chicago can be a spontaneous way to enjoy a long-distance trip without spending a fortune. We offer exclusive all-inclusive Chicago vacation packages (including flights, accommodations, meals, activities, and more), making it easy to save money without the stress of planning every detail. These deals are perfect for escaping on short notice.