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Maui Vacation Packages from $545

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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®
  Kaanapali Ocean Inn
Includes buy one get one FREE activity. Kids 17 and younger stay FREE.


3 nights with air from $545
  Outrigger Aina Nalu
One-Bedroom. Includes buy one get one FREE activity. FREE high-speed in-room and resort-wide internet access. NO Resort Fees. Kids 17 and younger stay FREE.
3 nights with air from $629
  Royal Lahaina Resort
Includes buy one get one FREE activity. Kids 17 and younger stay FREE.


3 nights with air from $729
  Aston Kaanapali Shores
Studio. Includes buy one get one FREE activity. Kids 17 and younger stay FREE.


3 nights with air from $745
  Sheraton Maui Resort & Spa
Includes buy one get one FREE activity. Kids 17 and younger stay FREE.


3 nights with air from $809
  The Westin Maui Resort & Spa
Mountain View. Includes buy one get one FREE activity. Daily continental breakfast for two. $20 resort credit per room per night. 15% spa discount. Kids 17 and younger stay FREE.
3 nights with air from $835
  Hyatt Regency Maui Resort & Spa
Includes buy one get one FREE activity. 1,000 Hyatt Gold Passport® Points per night. FREE Wi-Fi. Kids 18 and younger stay FREE.

3 nights with air from $905
  The Ritz-Carlton, Kapalua
Includes buy one get one FREE activity. Kids 17 and younger stay FREE.


3 nights with air from $1,019
  Andaz Maui-a concept by Hyatt
Includes buy one get one FREE activity. 500 Hyatt Gold Passport® Points per night. FREE Wi-Fi. Daily breakfast at Ka'ana Kitchen for two.


3 nights with air from $1,249
  Montage Kapalua Bay
One-Bedroom. Includes buy one get one FREE activity. 4th night FREE. Kids 12 and younger stay FREE.


4 nights with air from $2,505

More Great Deals

  Oahu
  Maui
  Kauai
  Hawaii Island






Rates are based on roundtrip air travel to/from Sacramento (SMF) to Maui and are per person, based on double occupancy. Advertised vacation rate(s) valid for departure 8/24/15. 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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