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Oahu Vacation Packages from $585

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Chicago Departures
Ask about $100 discount per person!
On 5-night vacation packages
Book by 5/31/15 for travel through 12/20/15
Buy One Activity, Get One Activity FREE
On 3-night vacation packages
Book by 5/31/15 for travel through 12/20/15
Pleasant Hawaiian Holidays®
   OHANA Waikiki East
Includes buy one get one FREE activity. Shopping and dining discount booklet. FREE direct dial local phone calls, USA & Canada. FREE high-speed in-room and resort-wide internet access. NO Resort Fees. Kids 17 & younger stay FREE.


3 nights with air from $585
   Park Shore Waikiki
Includes buy one get one FREE activity. Kids 17 & younger stay FREE.


3 nights with air from $705
   Pacific Beach Hotel
Includes buy one get one FREE activity. Kids 17 & younger stay FREE.


3 nights with air from $745
  Sheraton Waikiki
Includes buy one get one FREE activity. Reduced rate. Kids 17 & younger stay FREE.


3 nights with air from $769
  Aston Waikiki Sunset
One-Bedroom. Includes buy one get one FREE activity. Kids 17 & younger stay FREE.


3 nights with air from $779
   Outrigger Reef Waikiki Beach Resort
Includes buy one get one FREE activity. Shopping and dining discount booklet. FREE direct dial local phone calls, USA & Canada. FREE high-speed in-room and resort-wide internet access. FREE vow renewal. NO Resort Fees. Kids 17 & younger stay FREE.
3 nights with air from $839
   Moana Surfrider - A Westin Resort & Spa
Banyan City View. Includes buy one get one FREE activity. Daily breakfast for two at Surfrider Café. Two mai tais per day at Beach Bar.15% spa discount. Complimentary lei & tropical punch upon arrival.
3 nights with air from $839
  Hilton Hawaiian Village® Waikiki Beach Resort
Ocean View. Includes buy one get one FREE activity. Reduced rate. Kids 18 & younger stay FREE.


3 nights with air from $875
   The Royal Hawaiian, a Luxury Collection Resort
Historic Room. Includes buy one get one FREE activity. Daily continental breakfast for two. Two mai tais per day. 15% spa discount. Kids 17 & younger stay FREE.

3 nights with air from $889
   Embassy Suites® - Waikiki Beach Walk®
One-Bedroom Suite. Includes buy one get one FREE activity. Shopping and dining discount booklet. Complimentay full breakfast daily and nightly two hour cocktail reception. FREE direct dial local phone calls, USA & Canada. FREE high-speed in-room and resort-wide internet access. FREE vow renewal. NO Resort Fees. Kids 17 & younger stay FREE.
3 nights with air from $999
   The Kahala Hotel & Resort
Includes buy one get one FREE activity. Kids 17 & younger stay FREE.


3 nights with air from $1,019
   Aulani, A Disney Resort & Spa, Hawaii
Partial Ocean View. Includes buy one get one FREE activity. 50.00 spendable room credit per night. Complimentary high speed wireless internet access. Kids 17 & younger stay FREE.

4 nights with air from $1,449

More Great Deals

  Oahu
  Maui
  Kauai
  Hawaii Island






Rates are based on roundtrip air travel to/from San Jose (SJC). Advertised vacation rate(s) valid for departure 9/14/15 for Aulani, A Disney Resort & Spa and 8/24/15 for all other properties. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult.

HAWAII: BOGO Activity Offer: Valid on new bookings made 5/4 – 5/31/15 for travel 5/4 – 12/20/15. Minimum 3-night hotel accommodations at participating property and roundtrip airfare required. Activity must be booked and redeemed through a Pleasant Holidays Activity Center or Breakfast Orientation. When traveler purchases one Hawaii activity through Pleasant Holidays, he/she will receive a second activity of equal or lesser value free of charge for qualified bookings. Maximum value of complimentary activity is $500. Fees and surcharges are excluded and must be paid for both tours. Limit of one complimentary activity per booking. Certain restrictions apply. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]


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