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Pittsburgh Early Booking Deals

Best Vacation Packages from Pittsburgh

All-Inclusive Vacation Packages w/ Air

If you like to plan ahead with an early bird deal, look no further! With round-trip or non-stop air for winter, spring and summer from Pittsburgh 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.

CANCUN  ▪  RIVIERA MAYA  ▪  PUNTA CANA  ▪  JAMAICA  ▪  COZUMEL

Save Even More with Exclusive Non-Stop Flights

Save your spot on our VE exclusive, non-stop flights with a low $225 deposit! Here are some of our top picks or find the best deals from your departure city using the booking box on this page.

PITTSBURGH [PIT] 2025
Cancun ▪ 7-Nights ▪ Saturdays ▪ 2/15/25 - 8/2/25
Punta Cana ▪ 7-Nights ▪ Saturdays ▪ 1/4/25 - 8/9/25
Punta Cana ▪ 7-Nights ▪ Saturdays ▪ 10/11/25 - 12/27/25
Punta Cana ▪ 7-Nights ▪ Sundays ▪ 5/25/25 - 7/20/25

Punta Cana

Vista Sol Punta Cana
  • Save Up to 10%

ALL-INCLUSIVE PACKAGES WITH EXCLUSIVE NON-STOP FLIGHTS

7 Nights From:

$999*: Apr 5

 

$1149*: Jan 11

 

$1241*: Jul 5, Jul 12, Jul 19, Jul 26

 

$1388*: Feb 15

Cancun

ALL-INCLUSIVE PACKAGES WITH EXCLUSIVE NON-STOP FLIGHTS

7 Nights From:

$1099*: May 10, May 17

 

$1199*: Mar 8, Mar 15

 

$1243*-$1299*: Feb 15, Feb 22, Mar 1, Mar 22, Mar 29

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$1049*: 3/1-4/30

 

$1099*: 1/4-2/28

Cozumel

Grand Park Royal Cozumel
  • Up to 45% Off
  • Book Now & Save!

ALL-INCLUSIVE PACKAGES WITH EXCLUSIVE NON-STOP FLIGHTS - INCLUDES FERRY TRANSFERS TO COZUMEL

7 Nights From:

$1199*: Apr 26

 

$1264*: May 10, May 17

 

$1278*-$1394*: Feb 22, Mar 8, Mar 15, Apr 12, Apr 19

 

$1439*-$1506*: Feb 15, Mar 1, Mar 22, Mar 29, Apr 5

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$989*: 1/4-2/28

 

$1145*: 3/1-4/30

Riviera Maya

Platinum Yucatan Princess All Suites Resort & Spa
  • Adults-Only Getaway
  • Save Up to 48%

ALL-INCLUSIVE PACKAGES WITH EXCLUSIVE NON-STOP FLIGHTS

7 Nights From:

$1489*: Apr 26, May 10, May 17

 

$1692*-$2157*: Apr 5, Apr 12, Jul 5, Jul 12

 

$1977*: Feb 22, Mar 8, Mar 15

 

$2027*-$2077*: Feb 15, Mar 1, Mar 22, Mar 29

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$1529*: 1/4-2/28

 

$1559*: 3/1-4/30

Jamaica

ALL-INCLUSIVE PACKAGES WITH ROUND-TRIP FLIGHTS

5 Nights From:

$929*: 3/1-4/30

 

$1109*: 1/4-2/28

Trip Protection & Insurance

Traveling within three days? Our Travel Advisors can make it happen! Call 1-800-309-4717 to book.
*Ferry transfer from Cancun is included in the above exclusive non-stop flight package prices to Cozumel. 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 or Vacation Express public charter flights operated by Allegiant Air. 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 11/1/24. 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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