Title: All inclusive Vacations in Far North Side 2026 | Expedia.ca ![](https://images.trvl-media.com/place/553248635074842747/4c830a7f-a9f5-4e29-83f7-dc2e54b474ac.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Far North Side All inclusive Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by W. Ross Wells - ## 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 Far North Side Price found within the past 48 hours. Click for updated prices. ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $762 per person Mar 12 - Mar 15 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,229 reviews) Great experience with no problems Reviewed on Jan 27, 2026 ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $1,000 per person Mar 13 - Mar 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Great stay. Would come again. Reviewed on Jan 19, 2026 ![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 $980 per person Mar 13 - Mar 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Clean room and amenities Reviewed on Jan 8, 2026 ![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 $1,116 per person Mar 12 - Mar 15 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The room was boring thought it would be cleaner updated for the price best part was the view Reviewed on Jan 24, 2026 ![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Virgin Hotels Chicago Downtown Chicago CA $1,088 per person Mar 13 - Mar 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,404 reviews) Staff was super friendly and rooms were clean. Definitely will come back Reviewed on Jan 20, 2026 Don't see what you're looking for? See all available trips from Columbus to Far North Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-28/2026-03-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* All inclusive holidays in Far North 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 $1,116 per person Mar 12 - Mar 15 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The room was boring thought it would be cleaner updated for the price best part was the view Reviewed on Jan 24, 2026 ![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 $1,521 per person Mar 10 - Mar 14 found 16 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. Reviewed on Jan 26, 2026 ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago CA $1,526 per person Mar 10 - Mar 15 found 17 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Staff was wonderful. Reviewed on Jan 25, 2026 Don't see what you're looking for? See all available trips from Columbus to Far North Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-28/2026-03-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night All inclusive holidays in Far North Side Price found within the past 48 hours. Click for updated prices. ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $762 per person Mar 12 - Mar 15 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,229 reviews) Great experience with no problems Reviewed on Jan 27, 2026 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $850 per person Mar 12 - Mar 15 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Room was clean, comfortable and quiet. Reviewed on Jan 30, 2026 ![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 $1,116 per person Mar 12 - Mar 15 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The room was boring thought it would be cleaner updated for the price best part was the view Reviewed on Jan 24, 2026 Don't see what you're looking for? See all available trips from Columbus to Far North Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-28/2026-03-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night All inclusive holidays in Far North Side Price found within the past 48 hours. Click for updated prices. ![Aloft Chicago Downtown River North](https://images.trvl-media.com/lodging/6000000/5470000/5461400/5461400/w4000h2662x0y0-8993d93f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aloft Chicago Downtown River North Downtown Chicago CA $813 per person Mar 2 - Mar 6 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,159 reviews) Room and customer service was great! Reviewed on Jan 20, 2026 ![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 $845 per person Mar 2 - Mar 6 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.2/10 Wonderful! (317 reviews) Service was amazing and the location was perfect. Would definitely stay here again. Reviewed on Jan 28, 2026 ![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 $1,462 per person Mar 2 - Mar 6 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.6/10 Exceptional! (1,000 reviews) Everything was great… but the staff was absolutely amazing! Thank you for taking such great care of us. Reviewed on Jan 24, 2026 Don't see what you're looking for? See all available trips from Columbus to Far North Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-28/2026-03-07/?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 Far North Side including airfare with Expedia #### What are some benefits of booking an all-inclusive vacation? When you opt for an all-inclusive vacation to Far North 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 Far North 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 24\. #### Why should I book Far North Side vacations that are all inclusive and adults only? Adults-only stays in Far North 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 Far North 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 Far North Side? If you're looking to save, you'll find a wide range of prices available, ranging from CA $762\. By booking your accommodations and flight together, you may be able to enjoy savings of up to 24\. 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 Far North Side? If you've implemented the 5-star filter when searching for your all-inclusive vacation in Far North 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 Far North Side vacation packages that are all inclusive for the family? The most important thing to consider for all-inclusive family vacations to Far North 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 Far North Side's nightlife. #### How can I find the best deals on all-inclusive vacations in Far North 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 the Dominican Republic ](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/50/Dominican-Republic) ## More Vacations Ideas [Flights to Far North Side ](https://expedia.ca/Cheap-Flights-To-Far-North-Side.d553248635976475356.Travel-Guide-Flights)[ Far North Side Hotels ](https://expedia.ca/Far-North-Side-Hotels.d553248635976475356.Travel-Guide-Hotels)[ Far North Side Vacation Rentals ](https://expedia.ca/Far-North-Side-Vacation-Rentals.d553248635976475356.Travel-Guide-VacationRentals)[ Far North Side Car Rentals ](https://expedia.ca/Car-Rentals-In-Far-North-Side.d553248635976475356.Car-Rental-Guide)[ Far North Side Vacations ](https://expedia.ca/Far-North-Side.d553248635976475356.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. 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