All-inclusive vacation deals from Chicago (Midway) to Mexico and the Caribbean.

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Toggle including or excluding Adults Only experience packages, 6 deals match this criteria. Adults Only (6)

Toggle including or excluding All Inclusive experience packages, 15 deals match this criteria. All Inclusive (15)

Toggle including or excluding Beach experience packages, 13 deals match this criteria. Beach (13)

Toggle including or excluding Culture experience packages, 1 deals match this criteria. Culture (1)

Toggle including or excluding Dining experience packages, 14 deals match this criteria. Dining (14)

Toggle including or excluding Family experience packages, 10 deals match this criteria. Family (10)

Toggle including or excluding Gambling experience packages, 1 deals match this criteria. Gambling (1)

Toggle including or excluding Golfing experience packages, 7 deals match this criteria. Golfing (7)

Toggle including or excluding Mystery Deal experience packages, 4 deals match this criteria. Mystery Deal (4)

Toggle including or excluding Nightlife experience packages, 6 deals match this criteria. Nightlife (6)

Toggle including or excluding Romance experience packages, 10 deals match this criteria. Romance (10)

Toggle including or excluding Shopping experience packages, 2 deals match this criteria. Shopping (2)

Toggle including or excluding Skiing experience packages, 0 deals match this criteria. Skiing (0)

Toggle including or excluding Spa/Relaxation experience packages, 10 deals match this criteria. Spa/Relaxation (10)

Toggle including or excluding Sports experience packages, 0 deals match this criteria. Sports (0)

Toggle including or excluding $0 - $249 price range, 0 deals match this criteria. $0 - $249 (0)

Toggle including or excluding $250 - $499 price range, 0 deals match this criteria. $250 - $499 (0)

Toggle including or excluding $500 - $749 price range, 0 deals match this criteria. $500 - $749 (0)

Toggle including or excluding $750 + price range, 23 deals match this criteria. $750 + (23)

TBD TBD (0)

Toggle including or excluding 1.0 Hotel Rating:, 0 deals match this criteria. (0)

Toggle including or excluding 2.0 Hotel Rating:, 0 deals match this criteria. (0)

Toggle including or excluding 3.0 Hotel Rating:, 0 deals match this criteria. (0)

Toggle including or excluding 4.0 Hotel Rating:, 6 deals match this criteria. (6)

Toggle including or excluding 5.0 Hotel Rating:, 17 deals match this criteria. (17)

1 (0) Toggle including or excluding 1 nights packages, 0 deals match this criteria.

2 (0) Toggle including or excluding 2 nights packages, 0 deals match this criteria.

3 (2) Toggle including or excluding 3 nights packages, 2 deals match this criteria.

4 (3) Toggle including or excluding 4 nights packages, 3 deals match this criteria.

5 (18) Toggle including or excluding 5 nights packages, 18 deals match this criteria.

6 (0) Toggle including or excluding 6 nights packages, 0 deals match this criteria.

7+ (0) Toggle including or excluding 7+ nights packages, 0 deals match this criteria.

Hotel (a to z) Hotel (z to a) Destination (a to z) Destination (z to a) Rating (low to high) Rating (high to low) Our picks (top to bottom) Our picks (bottom to top) Results per page: 25 deals per page, currently set at 999. 25 50 deals per page, currently set at 999. 50 75 deals per page, currently set at 999. 75 Page: [1]

• 23 item(s) found , Page 1, 999 Results per page:
• Results per page: [25] 50 deals per page, currently set at 25. 50 75 deals per page, currently set at 25. 75
  

1. • 

   • Cancun - Riviera Maya Hotels

     Dreams Sands Cancun Resort & Spa Unlimited - Luxury®

     

     Save up to 50% + $200 resort coupons

     Valid departure date(s): 8/25 - 9/30

   • Cancun - Riviera Maya Hotels

     

     Dreams Sands Cancun Resort & Spa Unlimited - Luxury®

     Hotel Rating:

     Save up to 50% + $200 resort coupons

     3 nights hotel + flight - Click select to get price

     Valid departure date(s): 8/25 - 9/30

2. • 

   • Cancun - Cancun Hotels

     Reflect Cancun - Unlimited-Luxury®

     

     Save $250 + up to 50%

     Valid departure date(s): 8/25 - 12/23

   • Cancun - Cancun Hotels

     

     Reflect Cancun - Unlimited-Luxury®

     Hotel Rating:

     Save $250 + up to 50%

     5 nights hotel + flight - Click select to get price

     Valid departure date(s): 8/25 - 12/23

3. • 

   • Cancun - Riviera Maya Hotels

     Secrets Akumal Riviera Maya - Unlimited-Luxury®

     

     Save $250 + $200 resort coupons

     Valid departure date(s): 8/25 - 12/23

   • Cancun - Riviera Maya Hotels

     

     Secrets Akumal Riviera Maya - Unlimited-Luxury®

     Hotel Rating:

     Save $250 + $200 resort coupons

     4 nights hotel + flight - Click select to get price

     Valid departure date(s): 8/25 - 12/23

4. • 

   • Dominican Republic, Punta Cana

     Dreams Palm Beach Punta Cana - Unlimited Luxury®

     

     Save $250 + up to 50%

     Valid departure date(s): 8/25 - 12/19

   • Dominican Republic, Punta Cana

     

     Dreams Palm Beach Punta Cana - Unlimited Luxury®

     Hotel Rating:

     Save $250 + up to 50%

     5 nights hotel + flight - Click select to get price

     Valid departure date(s): 8/25 - 12/19

5. • 

   • Dominican Republic, Punta Cana

     Now Larimar Punta Cana - Unlimited-Luxury®

     

     Save $250 + up to 50%

     Valid departure date(s): 8/25 - 12/19

   • Dominican Republic, Punta Cana

     

     Now Larimar Punta Cana - Unlimited-Luxury®

     Hotel Rating:

     Save $250 + up to 50%

     5 nights hotel + flight - Click select to get price

     Valid departure date(s): 8/25 - 12/19

6. • 

   • Jamaica, Montego Bay

     Sunscape Splash Montego Bay - Unlimited-Fun®

     

     Save $250 + up to 50%

     Valid departure date(s): 8/25 - 12/19

   • Jamaica, Montego Bay

     

     Sunscape Splash Montego Bay - Unlimited-Fun®

     Hotel Rating:

     Save $250 + up to 50%

     5 nights hotel + flight - Click select to get price

     Valid departure date(s): 8/25 - 12/19

7. • 

   • Jamaica, Montego Bay

     Iberostar Grand Rose Hall - AI

     

     Save $250 + up to 35%

     Valid departure date(s): 8/25 - 12/19

   • Jamaica, Montego Bay

     

     Iberostar Grand Rose Hall - AI

     Hotel Rating:

     Save $250 + up to 35%

     5 nights hotel + flight - Click select to get price

     Valid departure date(s): 8/25 - 12/19

8. • 

   • Cancun - Riviera Maya Hotels

     Secrets The Vine Cancun - Unlimited-Luxury®

     

     Save $250 + $200 resort coupons

     Valid departure date(s): 8/25 - 12/23

   • Cancun - Riviera Maya Hotels

     

     Secrets The Vine Cancun - Unlimited-Luxury®

     Hotel Rating:

     Save $250 + $200 resort coupons

     4 nights hotel + flight - Click select to get price

     Valid departure date(s): 8/25 - 12/23

9. • 

   • Cancun - Riviera Maya Hotels

     Riu Palace Costa Mujeres - All-Inclusive

     

     Save $250 + $300 in instant savings

     Valid departure date(s): 8/25 - 12/23

   • Cancun - Riviera Maya Hotels

     

     Riu Palace Costa Mujeres - All-Inclusive

     Hotel Rating:

     Save $250 + $300 in instant savings

     5 nights hotel + flight - Click select to get price

     Valid departure date(s): 8/25 - 12/23

10. • 

    • Cancun - Cancun Hotels

      Mystery Deal - Adult-Only

      

      Save up to 60%

      Valid departure date(s): 8/25 - 12/23

    • Cancun - Cancun Hotels

      

      Mystery Deal - Adult-Only

      Hotel Rating:

      Save up to 60%

      4 nights hotel + flight - Click select to get price

      Valid departure date(s): 8/25 - 12/23

11. • 

    • Cancun - Riviera Maya Hotels

      Dreams Puerto Aventuras Resort & Spa - Unlimited-Luxury®

      

      Save $250 + up to 50%

      Valid departure date(s): 8/25 - 12/19

    • Cancun - Riviera Maya Hotels

      

      Dreams Puerto Aventuras Resort & Spa - Unlimited-Luxury®

      Hotel Rating:

      Save $250 + up to 50%

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 8/25 - 12/19

12. • 

    • Cancun - Riviera Maya Hotels

      Barcelo Maya Palace - All-Inclusive

      

      Save $250 + up to 30%

      Valid departure date(s): 8/25 - 1/4

    • Cancun - Riviera Maya Hotels

      

      Barcelo Maya Palace - All-Inclusive

      Hotel Rating:

      Save $250 + up to 30%

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 8/25 - 1/4

13. • 

    • Dominican Republic, Punta Cana

      Barcelo Bavaro Beach - All Inclusive

      

      Save up to 50% + $200 resort credits

      Valid departure date(s): 8/25 - 9/30

    • Dominican Republic, Punta Cana

      

      Barcelo Bavaro Beach - All Inclusive

      Hotel Rating:

      Save up to 50% + $200 resort credits

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 8/25 - 9/30

14. • 

    • Dominican Republic, Punta Cana

      Mystery Deal - Family

      

      A little bit of mystery. A whole lot of luxury.

      Valid departure date(s): 8/25 - 12/22

    • Dominican Republic, Punta Cana

      

      Mystery Deal - Family

      Hotel Rating:

      A little bit of mystery. A whole lot of luxury.

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 8/25 - 12/22

15. • 

    • Dominican Republic, Punta Cana

      TRS Turquesa Hotel - All-Inclusive, Adults Only

      

      Save $250 + exclusive shared transfer

      Valid departure date(s): 8/25 - 12/23

    • Dominican Republic, Punta Cana

      

      TRS Turquesa Hotel - All-Inclusive, Adults Only

      Hotel Rating:

      Save $250 + exclusive shared transfer

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 8/25 - 12/23

16. • 

    • Cancun - Riviera Maya Hotels

      Zoetry Paraiso de la Bonita Riviera Maya

      

      Save up to 50% + $200 resort coupons

      Valid departure date(s): 8/25 - 9/30

    • Cancun - Riviera Maya Hotels

      

      Zoetry Paraiso de la Bonita Riviera Maya

      Hotel Rating:

      Save up to 50% + $200 resort coupons

      3 nights hotel + flight - Click select to get price

      Valid departure date(s): 8/25 - 9/30

17. • 

    • Cancun - Riviera Maya Hotels

      Occidental at Xcaret Destination - AI

      

      Save up to 50% + $500 resort coupons

      Valid departure date(s): 8/25 - 12/22

    • Cancun - Riviera Maya Hotels

      

      Occidental at Xcaret Destination - AI

      Hotel Rating:

      Save up to 50% + $500 resort coupons

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 8/25 - 12/22

18. • 

    • Dominican Republic, Punta Cana

      Mystery Deal - Adult-Only

      

      A little bit of mystery. A whole lot of luxury.

      Valid departure date(s): 8/25 - 12/22

    • Dominican Republic, Punta Cana

      

      Mystery Deal - Adult-Only

      Hotel Rating:

      A little bit of mystery. A whole lot of luxury.

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 8/25 - 12/22

19. • 

    • Jamaica, Montego Bay

      Mystery Deal - Adult-Only

      

      Save up to 56%

      Valid departure date(s): 8/25 - 12/22

    • Jamaica, Montego Bay

      

      Mystery Deal - Adult-Only

      Hotel Rating:

      Save up to 56%

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 8/25 - 12/22

20. • 

    • Jamaica, Montego Bay

      Hideaway at Royalton Negril - AI

      

      Save $250 + up to 58%

      Valid departure date(s): 8/25 - 3/5

    • Jamaica, Montego Bay

      

      Hideaway at Royalton Negril - AI

      Hotel Rating:

      Save $250 + up to 58%

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 8/25 - 3/5

21. • 

    • Jamaica, Montego Bay

      Azul Beach Resort Negril by Karisma - All-Inclusive

      

      Save $250 + up to 54%

      Valid departure date(s): 8/25 - 3/5

    • Jamaica, Montego Bay

      

      Azul Beach Resort Negril by Karisma - All-Inclusive

      Hotel Rating:

      Save $250 + up to 54%

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 8/25 - 3/5

22. • 

    • Jamaica, Montego Bay

      Zoëtry Montego Bay Jamaica - Endless Privileges®

      

      Save up to 68% + $200 resort credits

      Valid departure date(s): 8/25 - 9/30

    • Jamaica, Montego Bay

      

      Zoëtry Montego Bay Jamaica - Endless Privileges®

      Hotel Rating:

      Save up to 68% + $200 resort credits

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 8/25 - 9/30

23. • 

    • Jamaica, Montego Bay

      Mystery Deal - Family

      

      Save up to 51%

      Valid departure date(s): 8/25 - 12/22

    • Jamaica, Montego Bay

      

      Mystery Deal - Family

      Hotel Rating:

      Save up to 51%

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 8/25 - 12/22

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