Title: All inclusive Vacations in Central Chicago 2026 | Expedia.ca ![](https://images.trvl-media.com/place/829/bd91735e-0c7e-4d0c-8152-a9d6fd38ff30.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Central Chicago All inclusive Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Phil Ostroff - ## 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 Central Chicago Price found within the past 48 hours. Click for updated prices. ![The Talbott, Autograph Collection](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/c6696bbf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Talbott, Autograph Collection Downtown Chicago CA $882 per person Apr 23 - Apr 26 found 14 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (85 reviews) Great location comfortable bed/pillows Reviewed on Mar 8, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $1,207 per person May 18 - May 22 found 12 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) Beautiful room. Property upgraded to 2-bedroom. Facilities are great with huge gym. Great stay in Chicago. Reviewed on Mar 14, 2026 ![JW Marriott Chicago](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/83e4c147_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### JW Marriott Chicago Downtown Chicago CA $928 per person Apr 23 - Apr 26 found 14 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.2/10 Wonderful! (1,007 reviews) The spa was wonderful, the room was clean and comfortable, and the staff was friendly. I only wish they had more food options. I have allergies and it was difficult to find items Reviewed on Mar 9, 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 $952 per person May 25 - May 28 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) The room was so clean, the staff were very kind and polite, helpful and made the hotel very welcoming!! The area was also safe and had lots of shopping areas and restaurants! 10/10 would recommend for everyone! Made my friend’s birthday wonderful! Thank you RIU! Reviewed on Mar 15, 2026 ![Kimpton Gray Hotel by IHG](https://images.trvl-media.com/lodging/14000000/13360000/13351500/13351499/9bf8883a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Gray Hotel by IHG Downtown Chicago CA $965 per person Apr 23 - Apr 26 found 14 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.2/10 Wonderful! (1,000 reviews) Everything was excellent, beautiful ! Reviewed on Mar 15, 2026 Don't see what you're looking for? See all available trips from Columbus to Central Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-15/2026-04-22/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* All inclusive holidays in Central Chicago Price found within the past 48 hours. Click for updated prices. ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $996 per person Apr 24 - Apr 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,844 reviews) Room was perfect/staff was great Reviewed on Mar 12, 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1ede47da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,680 per person Apr 23 - Apr 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,004 reviews) Nice bellmen, nice front staff, rooms were cozy and well kept. Everyone was very friendly and helpful. We would stay again. Reviewed on Mar 1, 2026 ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c8149674_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,254 per person Apr 24 - Apr 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,003 reviews) The room was a little dated. I was surprised that you didn’t have CNBC as a TV choice, I thought the gym was dated and the WiFi was inadequate Reviewed on Feb 28, 2026 Don't see what you're looking for? See all available trips from Columbus to Central Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-15/2026-04-22/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night All inclusive holidays in Central Chicago 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 $874 per person Apr 23 - Apr 26 found 14 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Great spot and view, would stay again! Reviewed on Mar 13, 2026 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $879 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,137 reviews) Great location, clean and very nice restaurant and bar. Reviewed on Mar 9, 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 $936 per person Apr 23 - Apr 26 found 14 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) The room was so clean, the staff were very kind and polite, helpful and made the hotel very welcoming!! The area was also safe and had lots of shopping areas and restaurants! 10/10 would recommend for everyone! Made my friend’s birthday wonderful! Thank you RIU! Reviewed on Mar 15, 2026 Don't see what you're looking for? See all available trips from Columbus to Central Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-15/2026-04-22/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night All inclusive holidays in Central Chicago Price found within the past 48 hours. Click for updated prices. ![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 $951 per person Apr 14 - Apr 18 found 15 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) The room was so clean, the staff were very kind and polite, helpful and made the hotel very welcoming!! The area was also safe and had lots of shopping areas and restaurants! 10/10 would recommend for everyone! Made my friend’s birthday wonderful! Thank you RIU! Reviewed on Mar 15, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $1,207 per person May 18 - May 22 found 12 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) Beautiful room. Property upgraded to 2-bedroom. Facilities are great with huge gym. Great stay in Chicago. Reviewed on Mar 14, 2026 ![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 $968 per person Apr 14 - Apr 18 found 15 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Great spot and view, would stay again! Reviewed on Mar 13, 2026 Don't see what you're looking for? See all available trips from Columbus to Central Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-15/2026-04-22/?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 Central Chicago including airfare with Expedia #### What are some benefits of booking an all-inclusive vacation? When you opt for an all-inclusive vacation to Central Chicago, 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 Central Chicago, 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 Central Chicago vacations that are all inclusive and adults only? Adults-only stays in Central Chicago 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 Central Chicago. 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 Central Chicago? If you're looking to save, you'll find a wide range of prices available, ranging from CA $874\. 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 Central Chicago? If you've implemented the 5-star filter when searching for your all-inclusive vacation in Central Chicago, 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 Central Chicago vacation packages that are all inclusive for the family? The most important thing to consider for all-inclusive family vacations to Central Chicago 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 Central Chicago's nightlife. #### How can I find the best deals on all-inclusive vacations in Central Chicago? 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. ## All inclusive Hotels in Central Chicago ![The Wheeler Mansion](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/18dd5e87_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Wheeler Mansion 2020 South Calumet Avenue Chicago IL - 6 min drive from Michigan Avenue Book a stay at this luxury hotel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Soldier Field and Grant Park are located ... [](https://expedia.ca/Chicago-Hotels-The-Wheeler-Mansion.h7818107.Hotel-Information) [See all 1,470 properties in Central Chicago](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248635976475413) 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. ## 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 Central Chicago ](https://expedia.ca/Cheap-Flights-To-Central-Chicago.d553248635976475413.Travel-Guide-Flights)[ Central Chicago Hotels ](https://expedia.ca/Central-Chicago-Hotels.d553248635976475413.Travel-Guide-Hotels)[ Central Chicago Vacation Rentals ](https://expedia.ca/Central-Chicago-Vacation-Rentals.d553248635976475413.Travel-Guide-VacationRentals)[ Central Chicago Car Rentals ](https://expedia.ca/Car-Rentals-In-Central-Chicago.d553248635976475413.Car-Rental-Guide)[ Central Chicago Vacations ](https://expedia.ca/Central-Chicago.d553248635976475413.Destination-Travel-Guides)[ Things to do in Central Chicago ](https://expedia.ca/Things-To-Do-In-Central-Chicago.d553248635976475413.Travel-Guide-Activities) \* 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. Scan the QR code with your device camera and download our app