Deals from ORD Airport
Deals from ORD Airport
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TripAdvisor Traveler Rating
TripAdvisor ReviewsCancunInstant Savings up to $500Dreams Aventuras Riviera Maya - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveRound-Trip Flights IncludedBest Priced Departure DatesJan 8, 20273 Nights Hotel + Flights Hotel + Flight + Taxes & FeesFrom $885 per person -
TripAdvisor Traveler Rating
TripAdvisor ReviewsCancunInstant Savings up to $500
Dreams Aventuras Riviera Maya - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveRound-Trip Flights IncludedBest Priced Departure DatesDec 2, 20263 Nights Hotel + Flights Hotel + Flight + Taxes & FeesFrom $815 per person -
Punta CanaInstant Savings up to $500Exclusive Offer
Dreams Cap Cana - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveRound-Trip Flights IncludedBest Priced Departure DatesJan 22, 20274 Nights Hotel + Flights Hotel + Flight + Taxes & FeesFrom $947 per person -
Punta Cana
Dreams Playa Esmeralda Resort & Spa - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveRound-Trip Flights IncludedBest Priced Departure DatesJan 25, 20274 Nights Hotel + Flights Hotel + Flight + Taxes & FeesFrom $1,231 per person -
TripAdvisor Traveler Rating
TripAdvisor ReviewsCancun
Hyatt Vivid Cancun - All Inclusive - Adults Only
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveRound-Trip Flights IncludedBest Priced Departure DatesJan 8, 20273 Nights Hotel + Flights Hotel + Flight + Taxes & FeesFrom $867 per person -
TripAdvisor Traveler Rating
TripAdvisor ReviewsCancun
Hyatt Vivid Cancun - All Inclusive - Adults Only
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveRound-Trip Flights IncludedBest Priced Departure DatesDec 14, 20263 Nights Hotel + Flights Hotel + Flight + Taxes & FeesFrom $824 per person -
Punta CanaInstant Savings up to $500Exclusive Offer
Hyatt Vivid Punta Cana Resort & Spa - All Inclusive - Adults Only
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveRound-Trip Flights IncludedBest Priced Departure DatesDec 14, 20264 Nights Hotel + Flights Hotel + Flight + Taxes & FeesFrom $1,053 per person -
TripAdvisor Traveler Rating
TripAdvisor ReviewsCancunInstant Savings up to $500Exclusive OfferDreams Tulum Resort & Spa - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveRound-Trip Flights IncludedBest Priced Departure DatesMar 2, 20273 Nights Hotel + Flights Hotel + Flight + Taxes & FeesFrom $913 per person -
TripAdvisor Traveler Rating
TripAdvisor ReviewsCancunInstant Savings up to $500Exclusive Offer
Dreams Tulum Resort & Spa - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveRound-Trip Flights IncludedBest Priced Departure DatesDec 14, 20263 Nights Hotel + Flights Hotel + Flight + Taxes & FeesFrom $823 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.