Title: Book the Best Downtown Chicago WINERY Hotels in 2026 | Expedia.ca [Downtown Chicago Travel Guide](https://expedia.ca/Chicago-Downtown-Chicago.dx6350699)[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)[Downtown Chicago Car Rentals](https://expedia.ca/Car-Rentals-In-Downtown-Chicago.d6350699.Car-Rental-Guide)[Downtown Chicago Vacations](https://expedia.ca/Downtown-Chicago.d6350699.Destination-Travel-Guides) ![Downtown Chicago showing a city](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Downtown Chicago, IL from CA $107 - ![](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 Downtown Chicago Winery Hotels Tonight [Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=6350699&startDate=2025-12-18&endDate=2025-12-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=6350699&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6350699&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6350699&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Downtown Chicago hotels with winery ![Lobby](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/b58d9761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### 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 (2445) "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 $154 total includes taxes & fees Dec 21 - Dec 22 [](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) ![Deluxe Suite, 1 King Bed, Non Smoking, Refrigerator (with Sofabed)](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/w5753h3840x5y0-9df2ab39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/3f32cdcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/0aca209a.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 (1024) "Clean,easy check-in." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $113 CA $132 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Chicago-Hotels-Best-Western-River-North-Hotel.h17227.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) ![Studio, 1 King Bed, Corner](https://images.trvl-media.com/lodging/1000000/10000/5600/5555/a30b8f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/1000000/10000/5600/5555/697017fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5600/5555/213d7224.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 (1001) "Nice staff, clean room " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim CA $152 CA $171 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Chicago-Hotels-Renaissance-Chicago-North-Shore-Hotel.h5555.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/9640f98d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/w3837h2559x3y0-4b7112a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/270c9b1b.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 (1000) "Really nice stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wenhui CA $146 CA $167 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Orrington-Evanston.h19722.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/97000000/96840000/96832200/96832125/16ec13d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/97000000/96840000/96832200/96832125/73c5897e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### STAY [](https://www.expedia.ca/Chicago-Hotels-Studio-424.h96832125.Hotel-Information) West Town 8.0/10 Very good (178) "I enjoyed my "STAY"! The covering for the dormitory bunk bead wa nice for privacy. The bed was clean. The other guest were extremely welcoming and pleasant. I'm reserving again already." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Johnnie CA $31 CA $107 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Chicago-Hotels-Studio-424.h96832125.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) ![Reception](https://images.trvl-media.com/lodging/1000000/560000/558000/557992/a2f5c82b.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) ![Indoor pool, open 6:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/560000/558000/557992/a50f01e2.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 (536) "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 25 - Dec 26 [](https://www.expedia.ca/Chicago-Hotels-Four-Points-By-Sheraton-Mt-Prospect-OHare.h557992.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=2026-01-01&endDate=2026-01-02®ionId=6350699&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Price trends for hotels in Downtown Chicago | Less expensive | More expensive | Next month | | -------------- | -------------- | ---------- | | January | October | CA $159 | | Month | Price | | --------- | ------- | | January | CA $159 | | February | CA $182 | | March | CA $240 | | April | CA $290 | | May | CA $424 | | June | CA $484 | | July | CA $406 | | August | CA $389 | | September | CA $470 | | October | CA $528 | | November | CA $394 | | December | CA $171 | Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Downtown Chicago. 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