Title: Downtown Chicago Vacation Packages & Trips 2025 from CA $505 | Expedia.ca [Downtown Chicago Travel Guide](https://expedia.ca/Chicago-Downtown-Chicago.dx6350699)[Hotels in Downtown Chicago](https://expedia.ca/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Downtown Chicago Car Rentals](https://expedia.ca/Car-Rentals-In-Downtown-Chicago.d6350699.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Downtown Chicago Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place ## Top Holiday Package Deals in Downtown Chicago Price found within the past 48 hours. Click for updated prices. ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $505 per person Jan 16 - Jan 19 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,110 reviews) We loved the Pendry! Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-19/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=vJpposegSqaEF0D5nI1Jfxl8R5zaK6rUQZzuf1acVFmohqG3Bqbru8tDlYZ9t1c7) ![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Michigan Avenue Chicago Downtown Chicago CA $908 per person Dec 21 - Dec 25 found 21 hours ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 8.8/10 Excellent! (1,070 reviews) Excellent staff all around. I will return. Reviewed on Oct 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-21/2025-12-25/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=2iNwDrKkiFnmTHALAc1c6IRZycc4oIxP6NEQ29ajSTZQzS3rnso6kWZo4IhMyo_C) ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $916 per person Dec 29 - Jan 3 found 22 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9/10 Wonderful! (367 reviews) Easy check-in, friendly staff, beautiful building with nice amenities. Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-03/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=2iNwDrKkiFnmTHALAc1c6EwV2EmPK2VnkYwdqOzvuKEUbw5XAWtXsLndzJmjg2MK) ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $525 per person Jan 16 - Jan 19 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,248 reviews) This hotel is amazing. The staff was so friendly and accommodating. The rooms were clean and the bed and pillows were so comfortable. Reviewed on Oct 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-19/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=vJpposegSqaEF0D5nI1Jfxl8R5zaK6rUQZzuf1acVFmObamnmuVqWy4P8mjFwV2C) ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $756 per person Jan 16 - Jan 19 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,761 reviews) The Trump never disappoints, always friendly, clean, and top notch service. We stay several times a year, they make you feel right at home. Reviewed on Oct 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-19/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=vJpposegSqaEF0D5nI1Jf0tHjjG4clxZggkTiDzmygmE6sFIxulEjmqmX-xFez5s) ## Where to stay in Downtown Chicago Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. [Learn more about Downtown Chicago](https://expedia.ca/Chicago-Downtown-Chicago.dx6350699) ![Magnificent Mile - River North](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24577-Magnificent-Mile.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Magnificent Mile Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service. [Find hotel + flight trips in Magnificent Mile](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Magnificent%20Mile&DestID=800025&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![The Loop - Downtown featuring a river or creek](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192013-The-Loop-Downtown.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### The Loop 4.5/5(725 area reviews) Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago. [Find hotel + flight trips in The Loop](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=The%20Loop&DestID=800024&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543369-chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### River North Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building. [Find hotel + flight trips in River North](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=River%20North&DestID=6350695&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Chicago which includes modern architecture and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54398-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Lincoln Park 5/5(20 area reviews) Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads. [Find hotel + flight trips in Lincoln Park](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Lincoln%20Park&DestID=6059328&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Chicago which includes rides](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23717-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Theatre District While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line). [Find hotel + flight trips in Theatre District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Theatre%20District&DestID=651190586167894016&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Downtown Chicago Hotel Deals ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St, Chicago, IL Fully refundableReserve now, pay when you stay CA $177 CA $208 total Nov 16 - Nov 17 includes taxes & fees 8.4/10 Very Good! (5,162 reviews) We enjoyed our stay, great location for walking around downtown. Reviewed on Oct 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=6350699) ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue, Chicago, IL Fully refundableReserve now, pay when you stay CA $131 CA $154 total Nov 24 - Nov 25 includes taxes & fees 7.8/10 Good! (9,592 reviews) From the moment we walked in the security was very friendly and helpful the first front desk attendant was amazing her name was Jasmine she was incredibly sweet helped us the best she could when we came back to do an early check-in the second person who helped us was incredibly rude service was terrible ... Reviewed on Oct 26, 2025 [](https://expedia.ca/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=6350699) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Magnificent Mile Suites 198 E Delaware Pl, Chicago, IL Fully refundableReserve now, pay when you stay CA $153 CA $180 total Nov 16 - Nov 17 includes taxes & fees 8.8/10 Excellent! (3,154 reviews) perfect !!! sad about the pool not being open Reviewed on Oct 26, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=6350699) [See all 1,726 properties in Downtown Chicago](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=29%2F10%2F2025&endDate=30%2F10%2F2025®ionId=6350699) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### How much does a Downtown Chicago vacation package cost? > Go from looking to booking with our Downtown Chicago vacation packages, which start from just CA $505. Handpick the hotels and flights that suit your travel style. Then, add on a couple of tours or activities for an amazing adventure. ### How do I get a cheap travel package to Downtown Chicago? > Bundle your bookings with Expedia to save big on your next trip. With more than 550 partner airlines and 1,000,000 hotels across the world, your Downtown Chicago vacation package can be tailored exactly to suit your budget. With all that extra money, why not include one or two fun tours and activities? It's an easy way to unlock even more savings. The vacation you've always dreamed of in Downtown Chicago is much closer than you thought! ### How far in advance should I book my Downtown Chicago vacation? > While not all airlines advertise tickets early, you can normally look up international airfares on Expedia up to 12 months in advance. This is the time you'll score some incredible deals. If you've left things to the last minute, you could still be in luck. Discounted prices occasionally emerge a few weeks before departure. ### What does an Expedia Downtown Chicago travel package include? > Packages include flights, hotels and rental cars, but you can mix and match them to create your ideal Downtown Chicago trip. You can also add on fun things like activities and tours once you've made your booking. You're in charge! When you combine your bookings with Expedia, you'll score discounts you won't find elsewhere. ### What should I know before booking a Downtown Chicago travel package? > Our prices are always low. However, you'll pick up even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and tons of choice. ### Can I choose my airline with a Downtown Chicago Expedia vacation package? > Yes — that's the beauty of an Expedia vacation package. You're in charge! We have more than 550 partner airlines throughout the world, so you have lots of choice when arranging your Downtown Chicago trip. ### If I'm not able to travel, can I cancel my Downtown Chicago vacation package? > You can. We understand that even the best-laid plans can go awry, so we're happy to help if you have to make changes to your Downtown Chicago vacation package. You may be able to change or cancel your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105) for further information. Also, be sure to check your itinerary for the finer details on change fees. ### Discover the most popular places to visit in Downtown Chicago ![Magnificent Mile - River North which includes signage, a city and night scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23728-Magnificent-Mile.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Michigan Avenue 4.5/5(19 reviews) You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. [](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) ![Navy Pier](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54738-Navy-Pier-Chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier 4.5/5(459 reviews) A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district. [](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction) ![Millennium Park featuring autumn colours, street scenes and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26436-Millennium-Park.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Millennium Park 4.5/5(722 reviews) A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape. [](https://expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction) ### Things to do ![River tour boat in Chicago](https://mediaim.expedia.com/localexpert/170432/2ab44ef1-1211-4f4f-9436-ce9a14d4241f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Architecture River Tour CA $68 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/architecture-river-tour.a170432.activity-details) ![Relax and enjoy the view](https://mediaim.expedia.com/localexpert/46106377/6686561e-a3aa-4cbf-9e71-f553bde2fa06.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Architecture Center River Cruise aboard First Lady CA $78 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/chicago-architecture-center-river-cruise-aboard-first-lady.a46106377.activity-details) ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/1b6e1be3-a6ba-4b3d-8e57-4d0336c3fd23.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket CA $47 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) [See all activities in Chicago](https://expedia.ca/things-to-do/search?rid=6350699) ## Explore a world of travel with Expedia - 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[Flights to Central Chicago](https://www.expedia.ca/Cheap-Flights-To-Central-Chicago.d553248635976475413.Travel-Guide-Flights) - [Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [900 North Michigan Shops](https://www.expedia.ca/900-North-Michigan-Shops-Downtown-Chicago.d6199347.Vacation-Attraction) - [Ann and Robert H. Lurie Children's Hospital](https://www.expedia.ca/Ann-And-Robert-H-Lurie-Childrens-Hospital-Downtown-Chicago.d553248624898453771.Vacation-Attraction) - [Aon Center](https://www.expedia.ca/Aon-Center-Downtown-Chicago.d6064015.Vacation-Attraction) - [Art Institute of Chicago](https://www.expedia.ca/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Vacation-Attraction) - [Buckingham Fountain](https://www.expedia.ca/Buckingham-Fountain-Downtown-Chicago.d6064027.Vacation-Attraction) - [Cibc Theatre](https://www.expedia.ca/CIBC-Theatre-Downtown-Chicago.d553248621563220853.Vacation-Attraction) - [Carbide and Carbon Building](https://www.expedia.ca/Carbide-And-Carbon-Building-Downtown-Chicago.d553248621555594910.Vacation-Attraction) - [Central Chicago Vacations](https://www.expedia.ca/Central-Chicago.d553248635976475413.Destination-Travel-Guides) - [Chicago Harbor Lighthouse](https://www.expedia.ca/Chicago-Harbor-Lighthouse-Chicago.d6064039.Vacation-Attraction) - [Chicago History Museum](https://www.expedia.ca/Chicago-History-Museum-Lincoln-Park.d6064041.Vacation-Attraction) - [Visit Magnificent Mile](https://www.expedia.ca/Chicago-Magnificent-Mile.dx800025) - [Chicago Riverwalk](https://www.expedia.ca/Chicago-Riverwalk-Downtown-Chicago.d553248621533116610.Vacation-Attraction) - [Visit Streeterville](https://www.expedia.ca/Chicago-Streeterville.dx6130109) - [Visit The Loop](https://www.expedia.ca/Chicago-The-Loop.dx800024) - [Chicago Theatre](https://www.expedia.ca/Chicago-Theatre-Downtown-Chicago.d6064049.Vacation-Attraction) - [Chicago Vacations](https://www.expedia.ca/Chicago.d178248.Destination-Travel-Guides) - [Visit Chicago](https://www.expedia.ca/Chicago.dx178248) - [Cloud Gate](https://www.expedia.ca/Cloud-Gate-Downtown-Chicago.d6182888.Vacation-Attraction) - [Grant Park](https://www.expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction) - [House of Blues Chicago](https://www.expedia.ca/House-Of-Blues-Chicago-Downtown-Chicago.d6227753.Vacation-Attraction) - [International Museum of Surgical Science](https://www.expedia.ca/International-Museum-Of-Surgical-Science-Downtown-Chicago.d6065139.Vacation-Attraction) - [John Hancock Center](https://www.expedia.ca/John-Hancock-Center-Downtown-Chicago.d6065131.Vacation-Attraction) - [Magnificent Mile Vacations](https://www.expedia.ca/Magnificent-Mile.d800025.Destination-Travel-Guides) - [Marina City](https://www.expedia.ca/Marina-City-Downtown-Chicago.d553248621533116577.Vacation-Attraction) - [Michigan Avenue](https://www.expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) - [Millennium Park](https://www.expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction) - [Navy Pier](https://www.expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction) - [Richard J. 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Savings not available on all packages.