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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191755-Chicago.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Winery Hotels in Downtown Chicago ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [24 Sept - 25 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=6350699&startDate=2025-09-24&endDate=2025-09-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [25 Sept - 26 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=6350699&startDate=2025-09-25&endDate=2025-09-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [26 Sept - 28 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=6350699&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [3 Oct - 5 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6350699&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Downtown Chicago Winery Hotels ## Our top choices for Downtown Chicago hotels with winery ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/19b0236f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/9378ca8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/aaae0504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed, Kitchenette | 1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/a9bc446d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Quarters Hotel, Central Loop, Chicago Downtown Chicago 8.8/10 Excellent (3370) "Very good place to stay" £127 includes taxes & fees 19 Oct - 20 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Club-Quarters-Hotel.h565746.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=2025-10-09&endDate=2025-10-10®ionId=6350699&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Downtown Chicago Hotel Reviews ## 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) - [Apartments in Central Chicago](https://www.expedia.co.uk/Central-Chicago-Apartments.d553248635976475413-aaApartments.Travel-Guide-Accommodation) - [B&B in Central Chicago](https://www.expedia.co.uk/Central-Chicago-Bed-And-Breakfasts.d553248635976475413-aaBedAndBreakfasts.Travel-Guide-Accommodation) - 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