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Hawaii Vacation Packages from $545

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Chicago Departures to Oahu and Maui
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®

3 nights from $565


3 nights from $545


3 nights from $669

More Great Deals
  Hawaii Island

Hawaii Island

3 nights from $689

Un-Cruise Adventures Hawaiian Seascapes

7 nights, cruise
only, from $3,605

More Hawaii Destinations

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Rates are based on roundtrip air travel from Oakland (OAK) to Oahu, Sacramento (SMF) to Maui, San Diego (SAN) to Kauai and Big Island based on double occupancy. Advertised vacation rate(s) valid for departure 8/17 for Hawaii Island, Kauai; 8/24/15 for Oahu and Maui; 9/14/15 to Kauai and Oahu; 11/7/15 for Un-Cruise Adventures Hawaiian Seascapes. 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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