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

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Hotel, Air, Car, Feature Hotel, Air, Car, Feature

Toggle including or excluding Adults Only experience packages, 3 deals match this criteria. Adults Only (3)

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

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

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

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

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

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

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

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

Toggle including or excluding Romance experience packages, 8 deals match this criteria. Romance (8)

Toggle including or excluding Shopping experience packages, 3 deals match this criteria. Shopping (3)

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

Toggle including or excluding Spa/Relaxation experience packages, 6 deals match this criteria. Spa/Relaxation (6)

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, 28 deals match this criteria. $750 + (28)

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:, 2 deals match this criteria. (2)

Toggle including or excluding 4.0 Hotel Rating:, 5 deals match this criteria. (5)

Toggle including or excluding 5.0 Hotel Rating:, 21 deals match this criteria. (21)

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 (1) Toggle including or excluding 3 nights packages, 1 deals match this criteria.

4 (1) Toggle including or excluding 4 nights packages, 1 deals match this criteria.

5 (26) Toggle including or excluding 5 nights packages, 26 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]

• 28 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 - Cancun Hotels

     Reflect Krystal Grand Cancun - Unlimited-Luxury®

     

     $200 in resort coupons + children stay free

     Valid departure date(s): 4/20 - 11/1

   • Cancun - Cancun Hotels

     

     Reflect Krystal Grand Cancun - Unlimited-Luxury®

     Hotel Rating:

     $200 in resort coupons + children stay free

     5 nights hotel + flight - Click select to get price

     Valid departure date(s): 4/20 - 11/1

2. • 

   • Cancun - Riviera Maya Hotels

     El Dorado Royale, a Spa Resort by Karisma - AI

     

     Save $150 + an extra 5,000 Rapid Rewards Points

     Valid departure date(s): 5/1 - 9/1

   • Cancun - Riviera Maya Hotels

     

     El Dorado Royale, a Spa Resort by Karisma - AI

     Hotel Rating:

     Save $150 + an extra 5,000 Rapid Rewards Points

     5 nights hotel + flight - Click select to get price

     Valid departure date(s): 5/1 - 9/1

3. • 

   • Cancun - Cancun Hotels

     Riu Dunamar - All Inclusive

     

     Save up to 52% + up to $300 in instant savings

     Valid departure date(s): 4/20 - 11/1

   • Cancun - Cancun Hotels

     

     Riu Dunamar - All Inclusive

     Hotel Rating:

     Save up to 52% + up to $300 in instant savings

     5 nights hotel + flight - Click select to get price

     Valid departure date(s): 4/20 - 11/1

4. • 

   • Cancun - Riviera Maya Hotels

     Secrets Capri Riviera Cancun - Unlimited-Luxury®

     

     Save up to 55% + $200 in resort coupons

     Valid departure date(s): 4/20 - 11/1

   • Cancun - Riviera Maya Hotels

     

     Secrets Capri Riviera Cancun - Unlimited-Luxury®

     Hotel Rating:

     Save up to 55% + $200 in resort coupons

     5 nights hotel + flight - Click select to get price

     Valid departure date(s): 4/20 - 11/1

5. • 

   • Dominican Republic, Punta Cana

     Dreams Palm Beach Punta Cana – All Inclusive

     

     Save up to $150 + up to 50%

     Valid departure date(s): 4/20 - 11/1

   • Dominican Republic, Punta Cana

     

     Dreams Palm Beach Punta Cana – All Inclusive

     Hotel Rating:

     Save up to $150 + up to 50%

     5 nights hotel + flight - Click select to get price

     Valid departure date(s): 4/20 - 11/1

6. • 

   • Cancun - Riviera Maya Hotels

     Iberostar Paraiso Maya - AI

     

     Save up to 35% + up to $800 in resort coupons

     Valid departure date(s): 4/20 - 11/1

   • Cancun - Riviera Maya Hotels

     

     Iberostar Paraiso Maya - AI

     Hotel Rating:

     Save up to 35% + up to $800 in resort coupons

     5 nights hotel + flight - Click select to get price

     Valid departure date(s): 4/20 - 11/1

7. • 

   • Dominican Republic, Punta Cana

     Chic Punta Cana - AI

     

     Save up to $150 + up to 60%

     Valid departure date(s): 4/20 - 11/1

   • Dominican Republic, Punta Cana

     

     Chic Punta Cana - AI

     Hotel Rating:

     Save up to $150 + up to 60%

     5 nights hotel + flight - Click select to get price

     Valid departure date(s): 4/20 - 11/1

8. • 

   • Jamaica, Montego Bay

     Breathless Montego Bay Resort & Spa - Unlimited-Luxury®?

     

     Save up to $150 + up to 50%

     Valid departure date(s): 4/20 - 11/1

   • Jamaica, Montego Bay

     

     Breathless Montego Bay Resort & Spa - Unlimited-Luxury®?

     Hotel Rating:

     Save up to $150 + up to 50%

     5 nights hotel + flight - Click select to get price

     Valid departure date(s): 4/20 - 11/1

9. • 

   • Jamaica, Montego Bay

     Azul Beach Resort Negril by Karisma - All-Inclusive

     

     Save $150 + 5,000 extra Rapid Rewards Points

     Valid departure date(s): 5/1 - 9/1

   • Jamaica, Montego Bay

     

     Azul Beach Resort Negril by Karisma - All-Inclusive

     Hotel Rating:

     Save $150 + 5,000 extra Rapid Rewards Points

     5 nights hotel + flight - Click select to get price

     Valid departure date(s): 5/1 - 9/1

10. • 

    • Jamaica, Montego Bay

      Riu Palace Tropical Bay - AI

      

      Save up to $150 + up to 32%

      Valid departure date(s): 4/20 - 11/1

    • Jamaica, Montego Bay

      

      Riu Palace Tropical Bay - AI

      Hotel Rating:

      Save up to $150 + up to 32%

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 4/20 - 11/1

11. • 

    • Cancun - Riviera Maya Hotels

      Azul Beach Resort Riviera Cancun By Karisma - All Inclusive

      

      Save $150 + an extra 5,000 Rapid Rewards Points

      Valid departure date(s): 5/1 - 9/1

    • Cancun - Riviera Maya Hotels

      

      Azul Beach Resort Riviera Cancun By Karisma - All Inclusive

      Hotel Rating:

      Save $150 + an extra 5,000 Rapid Rewards Points

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 5/1 - 9/1

12. • 

    • Cancun - Riviera Maya Hotels

      The Fives Azul Beach Resort Playa Del Carmen By Karisma - AI

      

      Save $150 + an extra 5,000 Rapid Rewards Points

      Valid departure date(s): 5/1 - 9/1

    • Cancun - Riviera Maya Hotels

      

      The Fives Azul Beach Resort Playa Del Carmen By Karisma - AI

      Hotel Rating:

      Save $150 + an extra 5,000 Rapid Rewards Points

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 5/1 - 9/1

13. • 

    • Cancun - Riviera Maya Hotels

      El Dorado Casitas Royale Spa Resort by Karisma -AI

      

      Save $150 + an extra 5,000 Rapid Rewards Points

      Valid departure date(s): 5/1 - 9/1

    • Cancun - Riviera Maya Hotels

      

      El Dorado Casitas Royale Spa Resort by Karisma -AI

      Hotel Rating:

      Save $150 + an extra 5,000 Rapid Rewards Points

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 5/1 - 9/1

14. • 

    • Cancun - Riviera Maya Hotels

      El Dorado Maroma, a Spa Resort by Karisma - AI

      

      Save $150 + an extra 5,000 Rapid Rewards Points

      Valid departure date(s): 5/1 - 9/1

    • Cancun - Riviera Maya Hotels

      

      El Dorado Maroma, a Spa Resort by Karisma - AI

      Hotel Rating:

      Save $150 + an extra 5,000 Rapid Rewards Points

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 5/1 - 9/1

15. • 

    • Cancun - Riviera Maya Hotels

      El Dorado Seaside Suites Spa Resort by Karisma-AI

      

      Save $150 + an extra 5,000 Rapid Rewards Points

      Valid departure date(s): 5/1 - 9/1

    • Cancun - Riviera Maya Hotels

      

      El Dorado Seaside Suites Spa Resort by Karisma-AI

      Hotel Rating:

      Save $150 + an extra 5,000 Rapid Rewards Points

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 5/1 - 9/1

16. • 

    • Cancun - Riviera Maya Hotels

      Generations Riviera Maya Spa Resort by Karisma -AI

      

      Save $150 + an extra 5,000 Rapid Rewards Points

      Valid departure date(s): 5/1 - 9/1

    • Cancun - Riviera Maya Hotels

      

      Generations Riviera Maya Spa Resort by Karisma -AI

      Hotel Rating:

      Save $150 + an extra 5,000 Rapid Rewards Points

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 5/1 - 9/1

17. • 

    • Cancun - Riviera Maya Hotels

      Barcelo Maya Beach & Caribe - AI

      

      Save up to 60% + up to $1000 in resort discounts

      Valid departure date(s): 4/20 - 6/23

    • Cancun - Riviera Maya Hotels

      

      Barcelo Maya Beach & Caribe - AI

      Hotel Rating:

      Save up to 60% + up to $1000 in resort discounts

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 4/20 - 6/23

18. • 

    • Cancun - Riviera Maya Hotels

      Barcelo Maya Colonial and Tropical Beach - AI

      

      Save up to 60% + up to $1000 in resort discounts

      Valid departure date(s): 4/20 - 6/23

    • Cancun - Riviera Maya Hotels

      

      Barcelo Maya Colonial and Tropical Beach - AI

      Hotel Rating:

      Save up to 60% + up to $1000 in resort discounts

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 4/20 - 6/23

19. • 

    • Dominican Republic, Punta Cana

      Grand Palladium Bavaro Suites Resort & Spa - AI

      

      Save up to $150 + up to 40%

      Valid departure date(s): 4/20 - 11/1

    • Dominican Republic, Punta Cana

      

      Grand Palladium Bavaro Suites Resort & Spa - AI

      Hotel Rating:

      Save up to $150 + up to 40%

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 4/20 - 11/1

20. • 

    • Dominican Republic, Punta Cana

      Nickelodeon Hotels & Resorts Punta Cana - AI

      

      Save $150 + up to 63%

      Valid departure date(s): 4/20 - 9/1

    • Dominican Republic, Punta Cana

      

      Nickelodeon Hotels & Resorts Punta Cana - AI

      Hotel Rating:

      Save $150 + up to 63%

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 4/20 - 9/1

21. • 

    • Dominican Republic, Punta Cana

      Now Onyx Punta Cana

      

      Save up to $150 + up to 50%

      Valid departure date(s): 4/20 - 11/1

    • Dominican Republic, Punta Cana

      

      Now Onyx Punta Cana

      Hotel Rating:

      Save up to $150 + up to 50%

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 4/20 - 11/1

22. • 

    • Dominican Republic, Punta Cana

      Riu Bambu - All Inclusive

      

      Save up to $150 + up to $200 in instant savings

      Valid departure date(s): 4/20 - 11/1

    • Dominican Republic, Punta Cana

      

      Riu Bambu - All Inclusive

      Hotel Rating:

      Save up to $150 + up to $200 in instant savings

      4 nights hotel + flight - Click select to get price

      Valid departure date(s): 4/20 - 11/1

23. • 

    • Dominican Republic, Punta Cana

      Secrets Cap Cana Resort & Spa - Unlimited-Luxury®

      

      Save up to $150 + up to 55%

      Valid departure date(s): 4/20 - 11/1

    • Dominican Republic, Punta Cana

      

      Secrets Cap Cana Resort & Spa - Unlimited-Luxury®

      Hotel Rating:

      Save up to $150 + up to 55%

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 4/20 - 11/1

24. • 

    • Dominican Republic, Punta Cana

      Zoëtry Agua Punta Cana – All Inclusive

      

      Save up to $150 + $200 in resort coupons

      Valid departure date(s): 4/20 - 11/1

    • Dominican Republic, Punta Cana

      

      Zoëtry Agua Punta Cana – All Inclusive

      Hotel Rating:

      Save up to $150 + $200 in resort coupons

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 4/20 - 11/1

25. • 

    • Jamaica, Montego Bay

      Zoëtry Montego Bay Jamaica - Endless Privileges®

      

      Save up to $150 + up to 50%

      Valid departure date(s): 4/20 - 11/1

    • Jamaica, Montego Bay

      

      Zoëtry Montego Bay Jamaica - Endless Privileges®

      Hotel Rating:

      Save up to $150 + up to 50%

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 4/20 - 11/1

26. • 

    • Jamaica, Montego Bay

      Royalton Blue Waters - AI

      

      Save up to $150 + up to 58%

      Valid departure date(s): 4/20 - 11/1

    • Jamaica, Montego Bay

      

      Royalton Blue Waters - AI

      Hotel Rating:

      Save up to $150 + up to 58%

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 4/20 - 11/1

27. • 

    • Jamaica, Montego Bay

      Royalton White Sands - AI

      

      Save up to $150 + up to 62%

      Valid departure date(s): 4/20 - 11/1

    • Jamaica, Montego Bay

      

      Royalton White Sands - AI

      Hotel Rating:

      Save up to $150 + up to 62%

      5 nights hotel + flight - Click select to get price

      Valid departure date(s): 4/20 - 11/1

28. • 

    • Jamaica, Montego Bay

      Holiday Inn Resort Montego Bay - AI

      

      Save up to $150 + up to 68%

      Valid departure date(s): 4/20 - 11/1

    • Jamaica, Montego Bay

      

      Holiday Inn Resort Montego Bay - AI

      Hotel Rating:

      Save up to $150 + up to 68%

      3 nights hotel + flight - Click select to get price

      Valid departure date(s): 4/20 - 11/1

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