Deals from ORD Airport
Deals from ORD Airport
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Limited time Steal of a Deal
Hyatt Vivid Playa del Carmen - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveCancun - Cancun AND Riviera MayaBest Priced Departure Dates2026: Jan 12, Jan 18, Jan 19, Jan 263 Nights Includes Taxes + Fees$1,033 per person -
TripAdvisor Traveler Rating
TripAdvisor ReviewsIncludes savings up to 78%Limited time steal of a dealHyatt Zilara Riviera Maya - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveCancun - Cancun AND Riviera MayaBest Priced Departure DatesMar 9, 20263 Nights Includes Taxes + Fees$849 per person -
TripAdvisor Traveler Rating
TripAdvisor ReviewsIncludes savings up to 20%Sunscape Cancun - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveCancun - Cancun AND Riviera MayaBest Priced Departure DatesJan 26, 20263 Nights Includes Taxes + Fees$908 per person -
TripAdvisor Traveler Rating
TripAdvisor Reviews
Sunscape Coco Punta Cana - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveDominican Republic, Punta CanaBest Priced Departure DatesDec 24, 20255 Nights Includes Taxes + Fees$1,463 per person -
Limited time Steal of a Deal
Hyatt Vivid Playa del Carmen - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveCancun - Cancun AND Riviera MayaBest Priced Departure Dates2026: Jan 12, Jan 19, Jan 263 Nights Includes Taxes + Fees$882 per person -
TripAdvisor Traveler Rating
TripAdvisor ReviewsIncludes savings up to 78%Limited time steal of a deal
Hyatt Zilara Riviera Maya - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveCancun - Cancun AND Riviera MayaBest Priced Departure Dates2026: Jan 19, Jan 263 Nights Includes Taxes + Fees$933 per person -
TripAdvisor Traveler Rating
TripAdvisor ReviewsIncludes savings up to 20%
Sunscape Cancun - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveCancun - Cancun AND Riviera MayaBest Priced Departure DatesJan 19, 20263 Nights Includes Taxes + Fees$708 per person -
TripAdvisor Traveler Rating
TripAdvisor Reviews
Dreams La Romana - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveDominican Republic, Punta CanaBest Priced Departure DatesFeb 21, 20263 Nights Includes Taxes + Fees$1,083 per person -
Hyatt Zilara Cap Cana - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveDominican Republic, Punta CanaBest Priced Departure DatesDec 21, 20253 Nights Includes Taxes + Fees$1,481 per person
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."
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.