Title: All inclusive Vacations in Northwest Side 2026/2026 | Expedia.ca ![](https://images.trvl-media.com/place/829/2253d64b-0974-4770-85a9-32842b88f38f.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Northwest Side All inclusive Vacations ## 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 ## Flight and All inclusive hotel deals in Northwest Side Price found within the past 48 hours. Click for updated prices. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $447 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) great staff...loved our stay. Reviewed on Nov 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=a27Pp9qmgRV6eid2GzNeKavKYWzblV5UCMXRFBoyloeEyJTCvGOfDnfSnqAUS_KG) ![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 $764 per person Feb 19 - Feb 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-22/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=1h-QEUGO7q1FgOFcC__mr3vhIDXWxsZpqf_oh70cEqbYSjFLL5slhNFsya_MqFb4) ![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 $676 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Its room was perfect the only bad part was their was a couple stains in the bathroom wall Reviewed on Dec 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&HotelClass=40&dealMarker=msY5_QYRkz8dm0P8LIGNs0Xt8ZeXWsJ5xl71nKK_P0V8u4KSa2bSEaxfvVVhk9Ca) ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $544 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in. Reviewed on Nov 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=95823687&paandie=true&HotelClass=40&dealMarker=2MaV768TBcz8HM99OhHJ6Nlv_u4Vf0Ni5r6K1-oMr8HpTp2lsdd0vXujlsmdIYiC) ![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 $792 per person Feb 19 - Feb 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful. Reviewed on Dec 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-22/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=1h-QEUGO7q1FgOFcC__mr3vhIDXWxsZpqf_oh70cEqZ9E8gvzBWMbVFuvLEq8X94) Don't see what you're looking for? See all available trips from Columbus to Northwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-02/2026-01-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* All inclusive holidays in Northwest Side Price found within the past 48 hours. Click for updated prices. ![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 $792 per person Feb 19 - Feb 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful. Reviewed on Dec 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-22/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=1h-QEUGO7q1FgOFcC__mr3vhIDXWxsZpqf_oh70cEqZ9E8gvzBWMbVFuvLEq8X94) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $865 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.6/10 Exceptional! (1,000 reviews) It is always an amazing place to stay Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=2MaV768TBcz8HM99OhHJ6Nlv_u4Vf0Ni5r6K1-oMr8FMQeuQsaJzxN1aNmvu-X2c) ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,048 per person Feb 19 - Feb 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) The staff was amazing. Will be making a return stay. Reviewed on Nov 30, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-22/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&HotelClass=50&dealMarker=1h-QEUGO7q1FgOFcC__mr2hOw_zF8H1fD-U9AxwEy57rvG1SsroBEv6A5If8SV5r) Don't see what you're looking for? See all available trips from Columbus to Northwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-02/2026-01-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night All inclusive holidays in Northwest Side Price found within the past 48 hours. Click for updated prices. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $377 per person Feb 19 - Feb 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) great staff...loved our stay. Reviewed on Nov 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-22/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=1h-QEUGO7q1FgOFcC__mryfvuo1wHAcKXLMOn5n0W-7ySHr2-wxAeGTABoxYCPNB) ![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 $764 per person Feb 19 - Feb 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-22/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=1h-QEUGO7q1FgOFcC__mr3vhIDXWxsZpqf_oh70cEqbYSjFLL5slhNFsya_MqFb4) ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $544 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in. Reviewed on Nov 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=95823687&paandie=true&HotelClass=40&dealMarker=2MaV768TBcz8HM99OhHJ6Nlv_u4Vf0Ni5r6K1-oMr8HpTp2lsdd0vXujlsmdIYiC) Don't see what you're looking for? See all available trips from Columbus to Northwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-02/2026-01-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night All inclusive holidays in Northwest Side Price found within the past 48 hours. Click for updated prices. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $447 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) great staff...loved our stay. Reviewed on Nov 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=a27Pp9qmgRV6eid2GzNeKavKYWzblV5UCMXRFBoyloeEyJTCvGOfDnfSnqAUS_KG) ![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 $676 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Its room was perfect the only bad part was their was a couple stains in the bathroom wall Reviewed on Dec 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=msY5_QYRkz8dm0P8LIGNs0Xt8ZeXWsJ5xl71nKK_P0V8u4KSa2bSEaxfvVVhk9Ca) ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago CA $719 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (317 reviews) The room was beautiful and clean and a good city view of the city Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=msY5_QYRkz8dm0P8LIGNsy1XodF78rXIk98U5jM4-6qq8FhhWb84LGypb6DZwhJ8) Don't see what you're looking for? See all available trips from Columbus to Northwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-02/2026-01-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Embark on an unforgettable all-inclusive trip to Northwest Side including airfare with Expedia #### What are some benefits of booking an all-inclusive vacation? When you opt for an all-inclusive vacation to Northwest Side, you can have everything you want to do planned out in advance. That means you get to simply coast through your vacation knowing exactly what's coming next. Plus, this helps you get a final tally on the costs beforehand, so it's much easier on your budget. #### Can I book all-inclusive packages with airfare and meals? Yes, all-inclusive vacation packages are readily available for Northwest Side, and you can search for them simply by using the search filter for all-inclusivity. When you book your flight along with your accommodations, you may even find some savings, with the potential to save up to 43. #### Why should I book Northwest Side vacations that are all inclusive and adults only? Adults-only stays in Northwest Side are good for travellers who are looking to relax in laid-back and easygoing surroundings. Everyone in the area will be looking to do much of the same without any kids to worry about, so you can truly take in some time for yourself in pampered bliss. Plus, you can filter for adults-only stays specifically in your search, so they're easy to find. #### Can I book all-inclusive packages? Yes, all-inclusive packages are fairly standard in Northwest Side. You can easily find all-inclusive options by using the search filters, but that's just the beginning. If you're booking at the last minute, you may even find additional discounts as properties try to fill their last remaining spots for cheap vacations that are all inclusive. #### Can I book cheap all-inclusive trips to Northwest Side? If you're looking to save, you'll find a wide range of prices available, ranging from CA $377. By booking your accommodations and flight together, you may be able to enjoy savings of up to 43. Be sure to sort your search results by price to list the cheapest options first. #### What should I look for when booking a 5-star all-inclusive vacation in Northwest Side? If you've implemented the 5-star filter when searching for your all-inclusive vacation in Northwest Side, there are a few factors to keep an eye out for. Spa access is particularly popular, as it's one of the best features you'll find in luxury accommodation options. Additionally, you should consider opting for an infinity pool and a luxury suite, especially if you're travelling with a relatively large group. #### What should I consider when booking Northwest Side vacation packages that are all inclusive for the family? The most important thing to consider for all-inclusive family vacations to Northwest Side is what your family is interested in. If your kids need access to a pool, you'll want to implement the search filter for that amenity. Kids' clubs can also be perfect for your family, as can babysitting services if the adults in your group plan on enjoying Northwest Side's nightlife. #### How can I find the best deals on all-inclusive vacations in Northwest Side? You can always sort your search results by price to automatically put the cheapest options at the top of your search while still considering all your implemented search filters. #### Can I book an all-inclusive package that is fully refundable? Yes, reservations that are fully refundable are available on some all-inclusive packages in . You can explore each package's cancellation policy in the policy section of their page, where you'll learn exactly how you can qualify. Sometimes, nothing is required to qualify. #### Why should I book an all-inclusive vacation with Expedia? Booking with Expedia makes it easy to find the ultimate all-inclusive vacation package. By offering accommodations and flights together, all-inclusive packages are easy for us to create and for you to enjoy. With benefits like being fully refundable and flexible dates on some packages, you can enjoy a more stree-free booking process. Expedia Rewards members can take that even further with the possibility of additional discounts. ## More vacations you might like ![](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) ### Top All inclusive Vacation Destinations > - 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[All inclusive vacations in Sosúa](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/601998/Sosua) > - [All inclusive vacations in the Dominican Republic](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/50/Dominican-Republic) ## More Vacations Ideas [Flights to Northwest Side](https://expedia.ca/Cheap-Flights-To-Northwest-Side.d553248635976475367.Travel-Guide-Flights)[Northwest Side Hotels](https://expedia.ca/Northwest-Side-Hotels.d553248635976475367.Travel-Guide-Hotels)[Northwest Side Vacation Rentals](https://expedia.ca/Northwest-Side-Vacation-Rentals.d553248635976475367.Travel-Guide-VacationRentals)[Northwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Northwest-Side.d553248635976475367.Car-Rental-Guide)[Northwest Side Vacations](https://expedia.ca/Northwest-Side.d553248635976475367.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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