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Deals from MKE Airport

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  • Nonstop Vacation Deal
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Includes savings up to 78%
    Limited time steal of a deal

    Hyatt Zilara Riviera Maya - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    2026: Feb 23, Mar 2, Mar 8, Mar 9, Mar 19
    3 Nights Hotel + Flight From
    $1,099 per person Includes Taxes + Fees
  • Nonstop Vacation Deal
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Includes savings up to 20%

    Sunscape Cancun - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    Mar 22, 2026
    3 Nights Hotel + Flight From
    $989 per person Includes Taxes + Fees
  • Nonstop Vacation Deal
    TripAdvisor Traveler Rating
    TripAdvisor Reviews

    Sunscape Coco Punta Cana - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Dominican Republic, Punta Cana
    Best Priced Departure Dates
    Feb 23, 2026
    3 Nights Hotel + Flight From
    $885 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Includes savings up to 78%
    Limited time steal of a deal

    Hyatt Zilara Riviera Maya - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    Mar 22, 2026
    3 Nights Hotel + Flight From
    $1,029 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Includes savings up to 20%

    Sunscape Cancun - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    Mar 22, 2026
    3 Nights Hotel + Flight From
    $906 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews

    Dreams La Romana - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Dominican Republic, Punta Cana
    Best Priced Departure Dates
    Mar 1, 2026
    3 Nights Hotel + Flight From
    $1,140 per person Includes Taxes + Fees

  • Hyatt Zilara Cap Cana - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Dominican Republic, Punta Cana
    Best Priced Departure Dates
    Dec 21, 2025
    3 Nights Hotel + Flight From
    $1,563 per person Includes Taxes + Fees

  • Hyatt Ziva Cap Cana - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Dominican Republic, Punta Cana
    Best Priced Departure Dates
    Feb 21, 2026
    3 Nights Hotel + Flight From
    $1,726 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews

    Sunscape Coco Punta Cana - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Dominican Republic, Punta Cana
    Best Priced Departure Dates
    2026: Feb 23, Feb 24
    3 Nights Hotel + Flight From
    $848 per person Includes Taxes + Fees
Not seeing deals? Modify your travel preferences, change your destination, or select new dates.

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.

Vacation Deals From Milwaukee FAQ

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.