Deals from MKE Airport
Deals from MKE 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 DatesFeb 9, 20263 Nights Includes Taxes + Fees$1,033 per person -
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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 Dates2026: Feb 23, Mar 2, Mar 8, Mar 9, Mar 193 Nights Includes Taxes + Fees$1,099 per person -
TripAdvisor Traveler Rating
TripAdvisor ReviewsIncludes savings up to 20%Sunscape Cancun - All Inclusive
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TripAdvisor ReviewsAll-InclusiveCancun - Cancun AND Riviera MayaBest Priced Departure DatesJan 30, 20263 Nights Includes Taxes + Fees$912 per person -
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TripAdvisor Reviews
Sunscape Coco Punta Cana - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveDominican Republic, Punta CanaBest Priced Departure DatesFeb 23, 20263 Nights Includes Taxes + Fees$772 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 DatesFeb 9, 20263 Nights Includes Taxes + Fees$1,033 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 DatesDec 20, 20253 Nights Includes Taxes + Fees$1,022 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$876 per person -
TripAdvisor Traveler Rating
TripAdvisor Reviews
Dreams La Romana - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveDominican Republic, Punta CanaBest Priced Departure DatesFeb 23, 20263 Nights Includes Taxes + Fees$1,110 per person -
Hyatt Zilara Cap Cana - All Inclusive
TripAdvisor Traveler Rating
TripAdvisor ReviewsAll-InclusiveDominican Republic, Punta CanaBest Priced Departure DatesFeb 9, 20263 Nights Includes Taxes + Fees$1,524 per person
If you’ve been dreaming of vacationing somewhere with ample sun and sand, let America’s favorite vacation company take care of securing the cheapest flights from Milwaukee. You and your loved ones can leave the stress and worry behind and treat yourselves to iconic destinations at all-inclusive resorts. Plant yourself beachside, enjoy fresh local seafood and international cuisine, play 18 holes surrounded by breathtaking views, and simply relax into pampering accommodations. Start your story with sea breezes and a cocktail in hand.
What destinations have the cheapest vacation deals from Milwaukee?
From Milwaukee, enjoy lush beach destinations and stunning waters with incredible wallet-friendly options that include Cancun and Riviera Maya, Acapulco, Punta Cana, Montego Bay, Puerto Vallarta, Aruba, and Hawaii. If you’re looking for something different, we also have cheap deals for Las Vegas, Orlando, and Phoenix.
How far in advance should I book from Milwaukee for the best price?
For cheap flights from Milwaukee, we recommend booking domestic travel within 1 to 3 months and international travel between 2 and 8 months out. If you’re planning to travel during peak season and the holidays, it’s better to allow more time.
Are last minute vacation deals from Milwaukee worth it?
If you’re the type who gets the travel bug on a whim, you’re in luck. We have incredible flight deals from Milwaukee within 60 days or less. Letting us take care of the details means you’ll be poolside before you know it. Easy mode activated.