Title: Book the Best Chicago WINERY Hotels in 2026 | 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) ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Chicago, IL from CA $97 - ![](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 [Dec 25 - Dec 26](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2025-12-25&endDate=2025-12-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2025-12-26&endDate=2025-12-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chicago hotels with winery ![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) ![Egyptian cotton sheets, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/279c3768.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 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) Downtown Chicago 8.2/10 Very good (2469) "Decent hotel in a great location with extremely helpful staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aaron CA $95 CA $153 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/6b178ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/f27cae17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds, Non Smoking (Larger Room)](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/ed3eaa7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/w5756h3835x5y5-bfca63cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western River North Hotel [](https://www.expedia.ca/Chicago-Hotels-Best-Western-River-North-Hotel.h17227.Hotel-Information) Downtown Chicago 7.8/10 Good (1023) "Clean,easy check-in." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $112 CA $131 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/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) ![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) ![Snack bar](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/86e1fd36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Publishing House B&B [](https://www.expedia.ca/Chicago-Hotels-The-Publishing-House-Bed-And-Breakfast.h19116049.Hotel-Information) Downtown Chicago 9.8/10 Exceptional (189) "Wonderful staff, beautiful hotel and great breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Veronica CA $308 CA $348 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/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/1000000/10000/5600/5555/9d2f9a0e.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) ![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) ### Renaissance Chicago North Shore Hotel [](https://www.expedia.ca/Chicago-Hotels-Renaissance-Chicago-North-Shore-Hotel.h5555.Hotel-Information) Northbrook 8.4/10 Very good (1000) "Nice staff, clean room " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim CA $161 CA $182 total includes taxes & fees Jan 3 - Jan 4, 2026 [](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) ![Presidential Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/e5a161cc.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 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Orrington-Evanston.h19722.Hotel-Information) Downtown Evanston 7.6/10 Good (1002) "Really nice stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wenhui CA $145 CA $166 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/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) ![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) ![Traditional Room, 2 Queen Beds | Bathroom](https://images.trvl-media.com/lodging/1000000/560000/558000/557992/a9cb9b76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Points by Sheraton Mt Prospect O'Hare [](https://www.expedia.ca/Chicago-Hotels-Four-Points-By-Sheraton-Mt-Prospect-OHare.h557992.Hotel-Information) Mount Prospect 8.0/10 Very good (537) "Great place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MOHAMMED CA $127 CA $144 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Chicago-Hotels-Four-Points-By-Sheraton-Mt-Prospect-OHare.h557992.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/120400/120330/bf81e567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/130000/120400/120330/cf957674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Schaumburg, IL [](https://www.expedia.ca/Chicago-Hotels-Country-Inn-Suites-By-Radisson.h120330.Hotel-Information) Schaumburg 8.8/10 Excellent (1147) "Breakfast was superior to most other stays" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donald CA $149 CA $171 total includes taxes & fees Jan 18 - Jan 19, 2026 [](https://www.expedia.ca/Chicago-Hotels-Country-Inn-Suites-By-Radisson.h120330.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 [](https://www.expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Waukegan.h283122.Hotel-Information) Waukegan 8.8/10 Excellent (1577) "Place was decent " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yesenia CA $129 CA $144 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Waukegan.h283122.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102860000/102855200/102855105/8d4ac94d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/103000000/102860000/102855200/102855105/431a27de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102860000/102855200/102855105/15cc0a72.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 [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Suites-Chicago-Schaumburg.h102855105.Hotel-Information) Schaumburg 9.4/10 Exceptional (197) "Friendly staff, very clean Comfortable room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $168 CA $198 total includes taxes & fees Jan 23 - Jan 24, 2026 [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Suites-Chicago-Schaumburg.h102855105.Hotel-Information) ![Lounge](https://images.trvl-media.com/lodging/1000000/490000/487700/487676/9552ef3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/490000/487700/487676/f2f6bf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/490000/487700/487676/20a2899c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room dining](https://images.trvl-media.com/lodging/1000000/490000/487700/487676/4f727ae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MainStay Suites Northbrook Wheeling [](https://www.expedia.ca/Chicago-Hotels-MainStay-Suites-Northbrook-Wheeling.h487676.Hotel-Information) Wheeling 7.6/10 Good (980) "I would say this hotel is amazing from the front staff to the room. The room is super clean. I’m happy with it. Definitely would recommend staying here." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyssa Marie CA $86 CA $97 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Chicago-Hotels-MainStay-Suites-Northbrook-Wheeling.h487676.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.ca/Hotel-Search?startDate=2026-01-08&endDate=2026-01-09®ionId=178248&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Chicago Hotel Reviews ## Frequently asked questions ### Which Chicago hotels are near the best wineries? > This charming 3.5-star bed and breakfast boasts an impressive guest rating of 9.8, making it a beloved choice among travellers. It features an on-site winery, allowing you to indulge in delightful wine tastings without having to venture far. Guests rave about the amazing breakfast, the great location, and the friendly staff, ensuring a relaxing and enjoyable stay. ### How much does a winery hotel in Chicago cost? ### Which winery hotels in Chicago offer wine tastings? > This 4-star hotel boasts an excellent guest rating of 9.4, making it a popular choice among travellers. It features an on-site tasting room where you can enjoy unique wine experiences and participate in exclusive release events. The hotel's location at Navy Pier adds to the allure, offering stunning views and easy access to Chicago's vibrant dining scene. > > > Guests rave about the clean and comfortable rooms, as well as the friendly and helpful staff. ### Which are the top Chicago winery hotels for couples? > Sable at Navy Pier Chicago, a 4-star hotel with a fantastic review rating of 9.4, offers an on-site tasting room and is great for couples looking to enjoy quality dining experiences. With its stunning views of Lake Michigan and the Chicago skyline, it provides a romantic atmosphere complemented by excellent service and great food. > > > The 3-star Country Inn & Suites by Radisson in Schaumburg, rated 8.8, is known for its convenient location near winery tours. It also features complimentary breakfast and free parking, making it an affordable choice for couples looking to explore the nearby wineries without breaking the bank. > > > Another great option is the Holiday Inn Express & Suites Chicago Schaumburg, which boasts a rating of 9.0\. This hotel is not only near winery tours but also offers spacious rooms and a delicious complimentary breakfast, making it a comfortable and convenient base for your wine country adventures. ### Which area of Chicago is best to stay in for vineyards and wineries? > For couples eager for a romantic escape, the intimate wine bars in Andersonville, such as the acclaimed "The Wine Cellar," offer a ideal setting to enjoy a selection of fine wines over candlelight. The neighbourhood's welcoming atmosphere and quaint boutiques make it an ideal backdrop for leisurely strolls hand-in-hand, creating cherished memories together. > > > Families will appreciate the family-friendly vibe of Andersonville, where spacious parks and community events provide entertainment for all ages. With activities like seasonal farmers' markets and outdoor concerts, there's always something fun happening, ensuring that everyone has an enjoyable time. ### Are there hotels in Chicago near winery tours? > The 3-star [Sonesta ES Suites Chicago Waukegan Gurnee](https://www.expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Waukegan.h283122.Hotel-Information) boasts a review rating of 9.0 and offers a great base for wine enthusiasts, with winery tours just a stone's throw away. Guests appreciate the friendly and helpful staff, as well as the clean and comfortable rooms. Plus, you can enjoy a complimentary breakfast on weekends to fuel your adventures. > > > Another excellent option is the [Country Inn & Suites by Radisson, Schaumburg, IL](https://www.expedia.ca/Chicago-Hotels-Country-Inn-Suites-By-Radisson.h120330.Hotel-Information), also rated 3 stars with a review score of 8.8\. This hotel features free breakfast and is known for its convenient location, making it easy to access nearby wineries. Guests have praised the friendly staff and spacious rooms, ensuring a pleasant stay. > > > The [Holiday Inn Express & Suites Chicago Schaumburg by IHG](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Suites-Chicago-Schaumburg.h102855105.Hotel-Information) is another 3-star choice with a rating of 9.0\. It offers a buffet breakfast and spacious, clean rooms, along with easy access to winery tours. The pool area is a lovely spot to unwind after a day of tasting, and guests appreciate the great service from the staff. > > > For those seeking a more upscale experience, the 4-star [Hotel Felix River North/Magnificent Mile](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) has a review rating of 8.2\. While it provides a stylish design, it's also close to winery tours, and guests have enjoyed its comfortable rooms and perfectly located setting. The fitness facilities are an added bonus for those wanting to stay active during their trip. > > > Lastly, the 3-star [TownePlace Suites by Marriott Chicago Waukegan/Gurnee](https://www.expedia.ca/Chicago-Hotels-TownePlace-Suites-By-Marriott-Chicago-WaukeganGurnee.h61203021.Hotel-Information), rated 9.0, is a comfortable and affordable option. It offers a complimentary breakfast and is well-reviewed for its helpful staff and nice amenities, all while being conveniently located near winery tours. ### What winery activities should we do in Chicago? > For couples seeking a romantic day out, consider the charming City Winery located right in downtown Chicago. This unique venue combines a working winery with a restaurant and live music, providing a superb atmosphere for an intimate evening. You can enjoy a glass of wine paired with a delicious meal while listening to local artists perform. > > > Families can also find enjoyment at the nearby wineries that host special events and activities for all ages. Some offer picnic areas and outdoor games, making it a great way to spend a sunny afternoon together. Children are often welcomed, allowing everyone to partake in the experience, from grape stomping to nature walks through the vineyards. > > > Wine enthusiasts will appreciate the educational tours offered at various vineyards, where you can delve deeper into the intricacies of viticulture and oenology. These tours often culminate in tastings, enhancing your understanding of the nuances in flavour and aroma, making it a rewarding outing. ### Does Chicago host any wine festivals or events? > For couples seeking a romantic outing, the Chicago Wine Fest offers a delightful experience in the heart of the city. Held during the summer months, this event invites you to stroll through beautiful gardens while sampling wines from various regions. It's the ideal setting for a leisurely afternoon, complete with live music and gourmet food pairings to enhance the experience. > > > Families can enjoy the array of wine-related events that often include educational components, like the Chicago Wine School's workshops. These classes provide a fun and informative way for families to learn about wine and food pairings, ensuring everyone can participate in the excitement, even if the adults are the primary tasters. > > > In addition, many local wineries and wine bars host seasonal events throughout the year, offering tastings that often include food pairings, live music, and festive atmospheres. These smaller gatherings can be a great way to engage with the local wine community while enjoying the city's diverse offerings. ### How can I save on a winery hotel in Chicago with Expedia? ### Is it cheaper to book flights and a winery hotel in Chicago as a package deal? ### Can I cancel my winery hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [2 Star Hotels in The Loop ](https://www.expedia.ca/2Star-The-Loop-Chicago-Hotels.s20-n800024-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in The Loop ](https://www.expedia.ca/3Star-The-Loop-Chicago-Hotels.s30-n800024-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in The Loop ](https://www.expedia.ca/4Star-The-Loop-Chicago-Hotels.s40-n800024-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in The Loop ](https://www.expedia.ca/5Star-The-Loop-Chicago-Hotels.s50-n800024-0.Travel-Guide-Filter-Hotels) - [Hotels near Adams-Wabash Station ](https://www.expedia.ca/Adams-Wabash-Station-Hotels.d6210258.Travel-Guide-Hotels) - 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