Title: TOP Winery Hotels in Downtown Chicago, IL for 2025 | Expedia.co.uk [Downtown Chicago Travel Guide](https://expedia.co.uk/Chicago-Downtown-Chicago.dx6350699)[Holiday Rentals in Chicago](https://expedia.co.uk/Chicago-Holiday-Rentals.d178248.Travel-Guide-HolidayRentals)[Flights to Chicago](https://expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.co.uk/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Downtown Chicago Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Downtown-Chicago.d6350699.Car-Hire-Guide)[Downtown Chicago Holidays](https://expedia.co.uk/Downtown-Chicago.d6350699.Holidays-City-Breaks) ![Downtown Chicago featuring a city](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Winery Hotels in Downtown Chicago - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Downtown Chicago Winery Hotels Tonight [27 Nov - 28 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6350699&startDate=2025-11-27&endDate=2025-11-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [28 Nov - 29 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6350699&startDate=2025-11-28&endDate=2025-11-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [28 Nov - 30 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6350699&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6350699&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Downtown Chicago Winery Hotels ![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 (2398) "Amazing stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Triston £86 includes taxes & fees 23 Dec - 24 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/f7f78ace.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) ![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) ![Premium Suite, 2 Double Beds, Non Smoking, Refrigerator (with Sofabed) | Pillow-top beds, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/aeb6fede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western River North Hotel Downtown Chicago 7.8/10 Good (1019) "Staff was very friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) david £77 includes taxes & fees 7 Dec - 8 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Best-Western-River-North-Hotel.h17227.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) ![Snack bar](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/86e1fd36.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) ### The Publishing House B&B Downtown Chicago 9.8/10 Exceptional (188) "Wonderful staff, beautiful hotel and great breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Veronica £154 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Chicago-Hotels-The-Publishing-House-Bed-And-Breakfast.h19116049.Hotel-Information) ![Courtyard](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/1000000/10000/5600/5555/1f90e38f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/5600/5555/cdfb97a7.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) ### Renaissance Chicago North Shore Hotel Northbrook 8.2/10 Very good (1008) "Breakfast was better than any surrounding hotels for sure." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LeeAnn £93 includes taxes & fees 19 Dec - 20 Dec [](https://www.expedia.co.uk/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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/9640f98d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 King Bed | Living area | 50-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/e5a161cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Orrington / Evanston Downtown Evanston 7.6/10 Good (1002) "Nice staff and easy access to the Northwestern campus. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia £91 includes taxes & fees 17 Dec - 18 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-Orrington-Evanston.h19722.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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/560000/558000/557992/d41e753f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional Room, 2 Queen Beds | Bathroom | Free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/560000/558000/557992/a9cb9b76.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) ### Four Points by Sheraton Mt Prospect O'Hare Mount Prospect 8.0/10 Very good (535) "Great place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MOHAMMED £79 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Four-Points-By-Sheraton-Mt-Prospect-OHare.h557992.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/918c1b0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/ea8d48e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/94fd527d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/fbb710a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 15mins DT | Wicker Park Gem | Sleeps 7 | FreePark East Garfield Park £252 includes taxes & fees 14 Dec - 15 Dec [](https://www.expedia.co.uk/Chicago-Hotels-15mins-DT-Wicker-Park-Gem-Sleeps-7-FreePark.h116934319.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/97000000/96840000/96832200/96832125/8f556219.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/97000000/96840000/96832200/96832125/a01fff59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/97000000/96840000/96832200/96832125/431b2916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Shared Dormitory (TOP BUNK TWIN FOR 1 GUEST ) | 1 bedroom, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/97000000/96840000/96832200/96832125/eedf1e0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### STAY West Town 8.0/10 Very good (174) "So incredibly clean, comfy bed, great shower and facilities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Braden £59 includes taxes & fees 11 Dec - 12 Dec [](https://www.expedia.co.uk/Chicago-Hotels-1415-Ashland-Ave.h96832125.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. [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2025-12-11&endDate=2025-12-12®ionId=6350699&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Downtown Chicago Hotel Reviews ![Club Quarters Hotel, Central Loop, Chicago](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/19b0236f_y.jpg) ### Club Quarters Hotel, Central Loop, Chicago 10/10 Excellent "Great stay, close to to cta , bus stop right in downtown " [](https://expedia.co.uk/Chicago-Hotels-Club-Quarters-Hotel.h565746.Hotel-Information) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - More ways to book - [Hotels near Aon Center](https://www.expedia.co.uk/Aon-Center-Hotels.0-l6064015-0.Travel-Guide-Filter-Hotels) - [Hotels near Carbide and Carbon Building](https://www.expedia.co.uk/Carbide-And-Carbon-Building-Hotels.0-l553248621555594910-0.Travel-Guide-Filter-Hotels) - [Serviced Apartments in Central Chicago](https://www.expedia.co.uk/Central-Chicago-Apart-Hotels.d553248635976475413-aaApartHotels.Travel-Guide-Accommodation) - 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[Car hire near Chicago](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Chicago.d178248.Car-Hire-Guide) - [Car hire near Cloud Gate](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Cloud-Gate.d6182888.Car-Hire-Guide) - [Car hire near Millennium Park](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Millennium-Park.d6069201.Car-Hire-Guide) - [Dollar Rent A Car Rental Cars in Central Chicago](https://www.expedia.co.uk/Dollar-Rent-A-Car-Car-Rentals-In-Central-Chicago.d553248635976475413-c43.Car-Rental-Guide-Suppliers) - [Europcar Rental Cars in Central Chicago](https://www.expedia.co.uk/Europcar-Car-Rentals-In-Central-Chicago.d553248635976475413-c14.Car-Rental-Guide-Suppliers) - [Full-Size Car Hire in Central Chicago](https://www.expedia.co.uk/Fullsize-Car-Rentals-In-Central-Chicago.d553248635976475413-tFullsize.Car-Rental-Guide-Class) - [Hertz Rental Cars in Central Chicago](https://www.expedia.co.uk/Hertz-Car-Rentals-In-Central-Chicago.d553248635976475413-c40.Car-Rental-Guide-Suppliers) - 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[Sports Car Car Hire near Millennium Park](https://www.expedia.co.uk/Sportscar-Car-Rentals-In-Millennium-Park.d6069201-tSportscar.Car-Rental-Guide-Class) - [Standard Car Hire in Central Chicago](https://www.expedia.co.uk/Standard-Car-Rentals-In-Central-Chicago.d553248635976475413-tStandard.Car-Rental-Guide-Class) - [Thrifty Car Rental Rental Cars in Central Chicago](https://www.expedia.co.uk/Thrifty-Car-Rental-Car-Rentals-In-Central-Chicago.d553248635976475413-c45.Car-Rental-Guide-Suppliers) - [People Carrier Car Hire near Cloud Gate](https://www.expedia.co.uk/Van-Car-Rentals-In-Cloud-Gate.d6182888-tVan.Car-Rental-Guide-Class) - [Central Chicago Holiday Rentals](https://www.expedia.co.uk/Central-Chicago-Holiday-Rentals.d553248635976475413.Travel-Guide-HolidayRentals) - [Things to do in Central Chicago](https://www.expedia.co.uk/Things-To-Do-In-Central-Chicago.d553248635976475413.Travel-Guide-Activities) - [Things to do in Chicago](https://www.expedia.co.uk/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities) - [Book Hotels in Downtown Chicago on Expedia.com](https://www.expedia.com/Downtown-Chicago-Chicago-Hotels-Winery-Hotel.0-n6350699-0-tWineryHotel.Travel-Guide-Filter-Hotels)