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Vacation Package Deals from Chicago, IL

*Please note, our featured "hot deals" are seasonal from all departure cities and are based on the destination as well as flight and hotel availability. Not all cities may be available yearround. Please use our search tool to the left for search all three of our featured vacation partners!

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Terms & Conditions: Vacation inclusions: Round trip air and hotel accommodations for specified number of nights. Select packages may be at All-Inclusive resorts and may include free transfers. See individual packages for details. Prices quoted are per person based on double occupancy, are not retroactive, and are subject to limited availability. All prices were current as of date posted. Fares are subject to change. Seats are limited and may not be available for all flights or dates of departure. Fuel surcharge of $95 - $120 is included in the price. Prices do not include additional baggage charges. Prices may vary and may be higher depending on actual day/date traveled and hotel selected. Valid only for new bookings made on VacationSuperSearch.com or with a VacationSuperSearch.com specialist. Hotel charges such as energy surcharge, baggage handling, crib, and rollaway costs may apply and are payable directly to hotel. The following per person charges are not included and are due with final payment: international fees and taxes up to $130.80, passenger facility charges up to $18, segment fees of $3.40 per domestic segment, a Hawaii arrival/departure tax of $15.00 (when applicable) and September 11th Security Fee up to $10. Various cancellation penalties, payment requirements and holiday/weekend/special event surcharges may apply, please contact a VacationSuperSearch.com specialist for details. All rates are subject to change with or without notice. Miles accrued on United Airlines flights are subject to the rules of the United Mileage Plus program. United and Mileage Plus are registered service marks.