Chicago to Hawaii deals - Specials travel deals and last minute sale for travel from Chicago.

Chicago to Hawaii deals - Specials travel deals and last minute sale for travel to the Hawaii Hawaii from Chicago.

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Chicago to Hawaii deals

Our company selects the best Chicago Hawaii deals and presents them on our website. The Chicago Hawaii deals are updated every Friday and are different every week. We include Chicago Hawaii vacation packages deals, Hawaii hotel deals, and airfare. Our goal is to save you time and money, it would take you hours of browsing to find these Chicago Hawaii deals on your own.

If you book a vacation package (hotel+airfare), you might save quite a bit of money, but if you have frequent flyer points or are not sure about the package or destination you want to purchase, give us a toll free call at 877 378 2140 during business hours or send us a request and our certified Hawaii experts will provide a few suggestions with pricing.

Below you will find our Chicago Hawaii deals sorted by price, and on the right column, Hawaii deals from major US cities:

Departure Destination Deal Price Nights Hotel Name-Rating Air Valid Day-Dates Description & Inclusions
Chicago Oahu packages deals $962 5 Aqua Continental - 1 UA Daily - 9/1-12/7/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes reduced rate - Check_Availability_3
Chicago Oahu packages deals $1,008 3 The Wyland Waikiki - 3 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes 3rd night FREE, daily continental breakfast, and guaranteed room upgrade. - Check_Availability_3
Chicago Oahu packages deals $1,031 3 Sheraton Princess Kaiulani - 3.5 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes reduced rate - Check_Availability_3
Chicago Oahu packages deals $1,040 3 Waikiki Beach Marriott Resort & Spa - 4 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes Reduced rate - Check_Availability_3
Chicago Kauai vacations deals $1,059 5 ResortQuest Kaua'i Beach Hotel at Makaiwa - 3.5 AS Wed, Thu - 9/10/08, 9/11/08, 10/1/08, 10/8/08, 10/22/08, 10/29/08, 10/30/08, 11/12/08 European Plan (not all inclusive) includes accommodations and hotel taxes. - Basic Gardenview Kids stay, play and eat FREE! Includes FREE Upgrade! - Check_Availability_1
Chicago Oahu packages deals $1,098 3 Outrigger Reef On The Beach - 4 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes reduced rate - Check_Availability_3
Chicago Oahu packages deals $1,128 3 Sheraton Waikiki - 4 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Ocean Front View. Includes reduced rate (Must be booked by 8/22/08) - Check_Availability_3
Chicago Maui vacations deals $1,142 6 ResortQuest Maui Ka'anapali Villas - 3 US Wed - 10/8/08 - 10/22/08 European Plan (not all inclusive) includes accommodations and hotel taxes. - Basic Stu/Gdv Kids stay, play, and eat FREE! - Check_Availability_1
Chicago Maui packages deals $1,145 3 ASTON Maui Lu - 1 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes Reduced rate - Check_Availability_3
Chicago Oahu vacation package deal $1,146 6 Wyland Hotel Waikiki - 3.5 UA Tue/Thu - 9/9 - 12/11 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - TWO FREE NIGHTS, Daily Continental Breakfast for two, Free upgrade to next available category and r/t transfers with lei greeting - Check_Availability_2
Chicago Maui packages deals $1,147 3 Lahaina Shores Beach Resort - 3 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes Reduced rate - Check_Availability_3
Chicago Oahu packages deals $1,149 3 Hyatt Regency Waikiki Resort & Spa - 4 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes 3rd night FREE, daily buffet breakfast for two & guaranteed room upgrade. - Check_Availability_3
Chicago Oahu packages deals $1,190 4 Hyatt Regency Waikiki Resort & Spa - Diamond Level - 4 UA Daily - 9/1-9/27/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - SunMex Vacations' Exclusive Diamond Level - Mountain View: Includes access to the Regency Club lounge with daily Hawaiian breakfast, afternoon snack and beverage service, evening cocktails and hors d'oeuvres, evening cordials, coffee and desserts. Plus, exclusive accommodations on the 24th floor, special check-in area, kids 12 & younger eat FREE, priority luggage handling, special in-room amenities, Hyatt courtesy car transportation service, access to the private sun deck and Jacuzzi, free parking, Regency Club Concierge services, nightly turndown service, daily newspaper and more! - Check_Availability_3
Chicago Molokai packages deals $1,194 3 Marc Hotel Molokai - 1 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - - Check_Availability_3
Chicago Oahu packages deals $1,200 3 ResortQuest Waikiki Beach - 4 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Partial Ocean View. Includes :Daily "Breakfast on the Beach", 2-for-1 luau, Aloha Book value coupons and Kids 12 & younger stay, play and eat FREE - Check_Availability_3
Chicago Oahu packages deals $1,226 3 Moana Surfrider, A Westin Resort - 4 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes Reduced rate - Check_Availability_3
Chicago Oahu vacations deals $1,245 5 ResortQuest Waikiki Beach Hotel - 3.5 UA Wed, Thu - 9/4/08 - 11/13/08, 12/3/08 European Plan (not all inclusive) includes accommodations and hotel taxes. - Htl Rm Partial OcnVw Nonstop service on United Airlines. Includes one night FREE, 2-for-1 luau and daily Breakfast on the Beach! Save over $300 per couple! - Check_Availability_1
Chicago Oahu packages deals $1,250 4 Hotel Renew an Aqua Elite - 3 UA Daily - 9/1-12/7/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes 4th night FREE - Check_Availability_3
Chicago Maui packages deals $1,251 3 ResortQuest at Papakea Resort - 3 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - One-Bedroom Ocean View. Includes reduced rate, Aloha Book value coupons and Kids 12 & younger stay, play and eat FREE - Check_Availability_3
Chicago Big Island packages deals $1,264 5 Uncle Billy's Kona Bay Hotel - 1 DL Daily - 9/1-12/7/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes daily continental breakfast Economy Car included - Check_Availability_3
Chicago Maui packages deals $1,288 3 ResortQuest Ka‘anapali Shores - 4 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes Aloha Book value coupons and Kids 12 & younger stay, play and eat FREE - Check_Availability_3
Chicago Maui packages deals $1,292 3 Outrigger Royal Kahana - 3 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Ocean View Studio. Includes reduced rate - Check_Availability_3
Chicago Kauai packages deals $1,306 5 ResortQuest Aloha Beach Hotel - 3 DL Daily - 9/1-12/7/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes reduced rate, Aloha Book value coupons and Kids 12 & younger stay, play and eat FREE Economy Car included - Check_Availability_3
Chicago Big Island packages deals $1,334 3 Sheraton Keauhou Bay Resort & Spa - 4.5 DL Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes reduced rate - Check_Availability_3
Chicago Kauai packages deals $1,351 3 Sheraton Kauai Resort - 4 DL Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes reduced rate - Check_Availability_3
Chicago Big Island vacations deals $1,387 5 Outrigger Fairway Villas - 4 UA Wed, Thu - 9/17/08-9/18/08, 9/24/08, 10/15/08-10/16/08, 10/22/08-10/23/08 European Plan (not all inclusive) includes accommodations and hotel taxes. - 2bdrm/2bath Golfview One night FREE, Postcards From Paradise and complimentary shopping tote! - Check_Availability_1
Chicago Oahu vacation package deal $1,401 6 Sheraton Waikiki - 4.5 UA Tue/Thu - 9/9 - 12/11 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - GREAT SAVINGS! Deluxe Ocean View and r/t transfers with lei greeting - Check_Availability_2
Chicago Oahu packages deals $1,406 3 The Kahala Hotel & Resort - 5 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes daily buffet breakfast for two - Check_Availability_3
Chicago Maui packages deals $1,441 3 Hyatt Regency Maui Resort & Spa - 5 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes 3rd night FREE, daily buffet breakfast for two & guaranteed room upgrade. - Check_Availability_3
Chicago Kauai vacations deals $1,446 5 The Westin Princeville Ocean Resort Villas - 4.5 AS Wed, Thu - 9/10/08, 9/11/08, 10/1/08, 10/8/08, 10/22/08, 10/29/08, 10/30/08, 11/12/08 European Plan (not all inclusive) includes accommodations and hotel taxes. - Islandvw Dlx Studio - Check_Availability_1
Chicago Maui vacation package deal $1,450 6 Maui Coast Hotel - 2.5 UA Tue/Thu - 9/9 - 12/11 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Two Free Nights and Hertz car rental with unlimited mileage - Check_Availability_2
Chicago Maui packages deals $1,461 3 Sheraton Maui Resort - 5 UA Daily - 9/16-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes reduced rate - Check_Availability_3
Chicago Oahu vacations deals $1,471 5 Hilton Hawaiian Village Resort & Spa, Ali'i Tower - 5 UA Wed, Thu - 9/4/08 - 10/30/08, 12/3/08 European Plan (not all inclusive) includes accommodations and hotel taxes. - Ali'i Gardenview Nonstop service on United Airlines. Includes one night FREE, $50 dining category and FREE one category room upgrade! - Check_Availability_1
Chicago Maui packages deals $1,481 3 Kaanapali Beach Club - 3 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - One-Bedroom Suite. Includes reduced rate and daily buffet breakfast for two adults and children 5 years & younger - Check_Availability_3
Chicago Kauai packages deals $1,490 3 The Westin Princeville Ocean Resort Villas - 4 DL Daily - 9/3-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes reduced rate - Check_Availability_3
Chicago Maui packages deals $1,490 3 The Westin Maui Resort & Spa - 5 UA Daily - 9/16-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes reduced rate - Check_Availability_3
Chicago Big Island packages deals $1,520 5 ResortQuest Kona by the Sea - 3 DL Daily - 9/1-12/7/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - One-Bedroom Suite. Includes 5th night FREE, Aloha Book value coupons and Kids 12 & younger stay, play and eat FREE Economy Car included - Check_Availability_3
Chicago Maui packages deals $1,537 3 The Westin Kaanapali Ocean Resort Villas - 5 UA Daily - 9/3-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes reduced rate - Check_Availability_3
Chicago Kauai packages deals $1,540 5 Hilton Kauai Beach Resort - 4 DL Daily - 9/1-12/7/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes 5th night FREE Economy Car included - Check_Availability_3
Chicago Lanai packages deals $1,546 3 Four Seasons Resort Lanai, The Lodge at Koele - 5 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Ask about a 4th night FREE - Check_Availability_3
Chicago Kauai packages deals $1,563 5 Outrigger Kiahuna Plantation - 4 DL Daily - 9/1-12/7/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - One-Bedroom Suite. Includes 5th night FREE Economy Car included - Check_Availability_3
Chicago Oahu vacations deals $1,569 6 Moana Surfrider, a Westin Resort - 4.5 UA Wed, Thu - 9/11/08 - 9/18/08, 10/8/08 - 11/13/08 European Plan (not all inclusive) includes accommodations and hotel taxes. - Cityview Nonstop service on United Airlines. Includes two nights FREE and $75 dining credit! Save $900 per couple! - Check_Availability_1
Chicago Kauai vacation package deal $1,607 6 Resortquest Kauai Beach - 3.5 CO Tue/Thu - 9/9 - 12/11 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Two Free Nights, $50 Food & Beverage Credit per room per stay. Aloha book, presented at check-in, containing hundreds of dollars in savings on meals, shopping and golf. Includes 2-for-1 Luau (one certificate per room) Hertz car rental with unlimited mileage - Check_Availability_2
Chicago Big Island packages deals $1,699 5 Hilton Waikoloa Village - 4.5 DL Daily - 9/1-12/7/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes Reduced rate & guaranteed upgrade to Deluxe Ocean View & free car rental Economy Car included - Check_Availability_3
Chicago Maui vacations deals $1,706 6 The Westin Maui Resort & Spa - 4.5 US Wed - 10/8/08 - 10/22/08 European Plan (not all inclusive) includes accommodations and hotel taxes. - Gardenview Includes 2 nights FREE, daily breakfast for two and a guaranteed one room category upgrade! - Check_Availability_1
Chicago Lanai packages deals $1,710 3 Four Seasons Resort Lanai at Manele Bay - 5 UA Daily - 9/1-12/9/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Ask about a 4th night FREE - Check_Availability_3
Chicago Big Island vacation package deal $1,891 6 Sheraton Keauhou Bay Resort & Spa - 4 AA Tue/Thu - 9/9 - 12/11 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - TWO FREE NIGHTS, Daily Buffet Breakfast and Hertz car rental with unlimited mileage - Check_Availability_2
Chicago Maui vacation package deal $1,999 6 Hyatt Regency Maui Resort & Spa - 5 UA Tue/Thu - 9/9 - 12/11 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - TWO FREE NIGHTS, Daily Buffet Breakfast, Free upgrade to Partial Ocean View, and Hertz car rental with unlimited mileage - Check_Availability_2
Chicago Kauai packages deals $2,035 5 Grand Hyatt Kauai Resort & Spa - 5 DL Daily - 9/1-12/7/08 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Includes 5th night FREE, daily buffet breakfast for two, guaranteed room upgrade. - Check_Availability_3
Chicago Kauai vacation package deal $2,068 6 Kauai Marriott Resort & Beach Club - 4.5 CO Tue/Thu - 9/9 - 12/11 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Free Night, upgade to Pool View, Daily Buffet Breakfast for two and Hertz car rental with unlimited mileage - Check_Availability_2
Chicago Maui vacation package deal $2,117 6 The Westin Maui Resort & Spa - 5 UA Tue/Thu - 9/9 - 12/11 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - Two Free Nights, Daily Breakfast Buffet for Two, DOUBLE upgrade to Ocean View and Hertz car rental with unlimited mileage - Check_Availability_2
Chicago Big Island vacation package deal $2,313 6 The Fairmont Orchid, Hawaii - 5 AA Tue/Thu - 9/9 - 12/11 European Plan (not all inclusive) includes accommodations, hotel taxes and round trip airport transfers. - TWO FREE NIGHTS, $200 Resort Credit, Daily Buffet Breakfast and Hertz car rental with unlimited mileage - Check_Availability_2
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Prices are per person, based on double occupancy and include: Air Only=round trip airfare; Hotel only=accommodations; European plan=accommodations plus round trip airfare and ground transportation, if all inclusive add meals, beverages, activities and tips. Services vary at each hotel, please view hotel description or call our reservation center for details. International airport taxes not included. These rates are subject to availability.

Our price guarantee: If any tour operator or vacation company has a lower price, we will match it and offer you a discount!

Chicago to Hawaii deals - Specials travel deals and last minute sale for travel from Chicago.
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