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Milwaukee Early Booking Deals

Best Vacation Packages from Milwaukee

All-Inclusive Vacation Packages w/ Round-Trip Air

If you like to plan ahead with an early bird deal, look no further! With round-trip air for fall and winter from Milwaukee and all-inclusive resorts, you'll find the perfect package to the Caribbean and Mexico. Find our best deals below or pick your ideal dates and shop using our booking box on this page.

PUNTA CANA  ▪  JAMAICA  ▪  COZUMEL  ▪  LOS CABOS

Cozumel

Iberostar Cozumel
  • Up to 35% Off
  • $300 Resort Credit††

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$1289*: 11/1-11/30

Punta Cana

Adults Only, Hideaway at Royalton Punta Cana Resort & Casino
  • Up to $600 Resort Credit††
  • Adults-Only Getaway

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$1319*: 11/1-11/30

Jamaica

Ocean Coral Spring
  • 1 Kid Stays, Plays & Eats Free

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$1489*: 11/1-11/30

Los Cabos

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$1814*: 11/1-11/30

Trip Protection & Insurance

Traveling within three days? Our Travel Advisors can make it happen! Call 1-800-309-4717 to book.
Kid's hotel offer based on one child per full paying guest and offered on select departures only; qualifying ages and maximum number of kids vary by resort and does not apply to airfare, transfers & booking fees. ††Restrictions apply. Call for details. *$1289 price is based on travel from Milwaukee to Iberostar Cozumel for 5 nights on November 13. Advertised prices available for bookings made electronically through your travel agent or on vacationexpress.com; small service fee of $10 applies when booking through Vacation Express Call Center. Prices are per person, based on double occupancy. For full terms and conditions, hotel information and description of all services, please refer to vacationexpress.com or call for details. Some upgrades are subject to availability upon check-in. Packages above are limited and subject to change without prior notice and are based on travel on coach/economy air with Spirit Airlines, American Airlines or other U.S. certified carriers. Airfares are per person, reflect lowest available airfare at time of printing, are subject to change and are based upon availability of class of service. Baggage charges and allowances vary by carrier and can change frequently. Most major carriers are charging a fee for checked baggage. Some airlines, including Spirit Airlines, are charging a fee for all checked and carry-on baggage. Clients must check their respective airline for the most current baggage information. Some hotels in the Cancun, Riviera Maya, Isla Mujeres and Cozumel areas of Mexico charge an environment fee of approximately $1.21 per room, per night. Fees are subject to change without notice and are payable at the hotel. Book by 8/12/22. Not responsible for errors or omissions. Registered Florida Seller of Travel no. St 38441. State of California Seller of Travel Certificate of Registration #2107538-40.

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