Title: Book the Best Chicago WINERY Hotels in 2025 | Expedia.ca [Chicago Travel Guide](https://expedia.ca/Chicago.dx178248)[Hotels in Chicago](https://expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels)[Vacation Rentals in Chicago](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[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)[Chicago Car Rentals](https://expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)[Chicago Vacation Packages](https://expedia.ca/Chicago.d178248.Destination-Travel-Guides) ![Chicago featuring heritage elements, signage and a high-rise building](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/237000/237257-Chicago.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Chicago, IL from CA $106 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chicago Winery Hotels Tonight [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2025-10-11&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chicago Winery Hotels ![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/f7f78ace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/f9eed5f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/520a670b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/b6152ff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western River North Hotel Downtown Chicago 7.8/10 Good (1021) "Great stay" CA $142 CA $166 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Best-Western-River-North-Hotel.h17227.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![City view from property](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/2b1c0fd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d2b26aad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/9097f753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Felix River North/Magnificent Mile Downtown Chicago 8.2/10 Very good (2265) "Hotel was nice, staff were friendly, and near attractions and restaurants " CA $118 CA $181 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![Staircase](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/5b0f48e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/73e82d38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/a2ea72ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/6cf646d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Publishing House B&B Downtown Chicago 9.8/10 Exceptional (186) "Wonderful staff, beautiful hotel and great breakfast!" CA $286 CA $323 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chicago-Hotels-The-Publishing-House-Bed-And-Breakfast.h19116049.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/5600/5555/ad7e3a92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/5600/5555/9d2f9a0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Down comforters, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/10000/5600/5555/cee1bbea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/5600/5555/1f90e38f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renaissance Chicago North Shore Hotel Northbrook 8.2/10 Very good (1001) "Relaxing, convenient and quiet. The staff are beyond sweet " CA $165 CA $186 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Chicago-Hotels-Renaissance-Chicago-North-Shore-Hotel.h5555.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/w3837h2560x3y0-c6a43ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/57f153c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/9640f98d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Orrington / Evanston Downtown Evanston 7.6/10 Good (1003) "Good stay" CA $201 CA $230 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Orrington-Evanston.h19722.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/120400/120330/41e5f2c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/130000/120400/120330/05bb993e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/120400/120330/bf81e567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/130000/120400/120330/d13d3b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Schaumburg, IL Schaumburg 8.8/10 Excellent (1081) "Awesome hotel." CA $139 CA $159 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Country-Inn-Suites-By-Radisson.h120330.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/560000/558000/557992/c763bdbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/560000/558000/557992/8308baeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/560000/558000/557992/a2f5c82b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/560000/558000/557992/d41e753f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Points by Sheraton Mt Prospect O'Hare Mount Prospect 8.0/10 Very good (532) "Great place to stay." CA $154 CA $174 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Chicago-Hotels-Four-Points-By-Sheraton-Mt-Prospect-OHare.h557992.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/290000/283200/283122/bfa6f6a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/290000/283200/283122/59446025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/290000/283200/283122/d109c830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/283200/283122/f0653ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta ES Suites Chicago Waukegan Gurnee Waukegan 9.0/10 Wonderful (1447) "Great hotel with everything you need. " CA $154 CA $173 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Waukegan.h283122.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/62000000/61210000/61203100/61203021/3ebe1c51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/62000000/61210000/61203100/61203021/799cdc10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/62000000/61210000/61203100/61203021/6b5965bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/62000000/61210000/61203100/61203021/672e6b0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TownePlace Suites by Marriott Chicago Waukegan/Gurnee Waukegan 9.2/10 Wonderful (139) "Very friendly staff, good breakfast, clean and spacious room." CA $178 CA $199 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chicago-Hotels-TownePlace-Suites-By-Marriott-Chicago-WaukeganGurnee.h61203021.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/103000000/102860000/102855200/102855105/24d9b89b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/103000000/102860000/102855200/102855105/42b35509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/103000000/102860000/102855200/102855105/091dd5fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102860000/102855200/102855105/d4d5fd7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Chicago Schaumburg by IHG Schaumburg 9.0/10 Wonderful (203) "clean, quiet, accessible, nice hotel." CA $167 CA $196 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Suites-Chicago-Schaumburg.h102855105.Hotel-Information) 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. 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[Kimpton Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Kimpton-Hotels.0-n800024-0--bKimptonHotels.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-LGBT-Friendly-Hotel.0-n800024-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Lake Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Lake-Hotels.0-n800024-0-tLakeHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Luxury-Hotel.0-n800024-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Marriott-Hotels-Resorts.0-n800024-0--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Oceanfront-Hotels.0-n800024-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Pet-Friendly-Hotel.0-n800024-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Romantic-Hotel.0-n800024-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Shopping Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Shopping-Hotel.0-n800024-0-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Ski-Hotel.0-n800024-0-tSkiHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Spa-Hotel.0-n800024-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [The Loop Hotels](https://www.expedia.ca/The-Loop-Chicago-Hotels.0-n800024-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Theatre District](https://www.expedia.ca/Theatre-District-Chicago-Hotels-Cheap-Hotels.0-n651190586167894016-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Theatre District](https://www.expedia.ca/Theatre-District-Chicago-Hotels-Luxury-Hotel.0-n651190586167894016-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Theatre District Hotels](https://www.expedia.ca/Theatre-District-Chicago-Hotels.0-n651190586167894016-0.Travel-Guide-Filter-Hotels) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Cibc Theatre](https://www.expedia.ca/CIBC-Theatre-Downtown-Chicago.d553248621563220853.Vacation-Attraction) - [Visit Downtown Chicago](https://www.expedia.ca/Chicago-Downtown-Chicago.dx6350699) - [Visit The Loop](https://www.expedia.ca/Chicago-The-Loop.dx800024) - [Millennium Park](https://www.expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction) - [Richard J. Daley Center](https://www.expedia.ca/Richard-J-Daley-Center-Downtown-Chicago.d6175173.Vacation-Attraction) - [The Loop Vacations](https://www.expedia.ca/The-Loop.d800024.Destination-Travel-Guides) - [Alamo Rent A Car Rental Cars in The Loop](https://www.expedia.ca/Alamo-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c6.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in The Loop](https://www.expedia.ca/Avis-Car-Rentals-In-The-Loop.d800024-c41.Car-Rental-Guide-Suppliers) - [Car rentals near Richard J. Daley Center](https://www.expedia.ca/Car-Rentals-In-Richard-J-Daley-Center.d6175173.Car-Rental-Guide) - [Car rentals near The Loop](https://www.expedia.ca/Car-Rentals-In-The-Loop.d800024.Car-Rental-Guide) - [Dollar Rent A Car Rental Cars in The Loop](https://www.expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c43.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in The Loop](https://www.expedia.ca/Enterprise-Car-Rentals-In-The-Loop.d800024-c15.Car-Rental-Guide-Suppliers) - [Fox Rental Cars Rental Cars in The Loop](https://www.expedia.ca/Fox-Rental-Cars-Car-Rentals-In-The-Loop.d800024-c19.Car-Rental-Guide-Suppliers) - [Oryx Rent A Car Rental Cars in The Loop](https://www.expedia.ca/ORYX-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c1059.Car-Rental-Guide-Suppliers) - [Payless Rental Cars in The Loop](https://www.expedia.ca/Payless-Car-Rentals-In-The-Loop.d800024-c38.Car-Rental-Guide-Suppliers) - [Rent A Wreck Rental Cars in The Loop](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-The-Loop.d800024-c33.Car-Rental-Guide-Suppliers) - [Routes Rental Cars in The Loop](https://www.expedia.ca/Routes-Car-Rentals-In-The-Loop.d800024-c1101.Car-Rental-Guide-Suppliers) - [Sixt Rental Cars in The Loop](https://www.expedia.ca/Sixt-Car-Rentals-In-The-Loop.d800024-c35.Car-Rental-Guide-Suppliers) - [Thrifty Car Rental Rental Cars in The Loop](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-The-Loop.d800024-c45.Car-Rental-Guide-Suppliers) - [Book Winery Hotels in Chicago on Expedia.com](https://www.expedia.com/Chicago-Hotels-Winery-Hotel.0-0-d178248-tWineryHotel.Travel-Guide-Filter-Hotels)