Title: Book the Best The Loop WINERY Hotels in 2026 | Expedia.ca [The Loop Travel Guide](https://expedia.ca/Chicago-The-Loop.dx800024)[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)[The Loop Car Rentals](https://expedia.ca/Car-Rentals-In-The-Loop.d800024.Car-Rental-Guide)[The Loop Vacations](https://expedia.ca/The-Loop.d800024.Destination-Travel-Guides) ![The Loop - Downtown featuring a river or creek](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in The Loop, 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 The Loop Winery Hotels Tonight [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=800024&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=800024&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=800024&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=800024&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for The Loop hotels with winery ![Business centre](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/0aca209a.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) ![Suite, 1 King Bed, Non Smoking, Refrigerator](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/ec554f43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/b9a3a586.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 (1027) "Loved it will be back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Antonio CA $113 CA $132 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Chicago-Hotels-Best-Western-River-North-Hotel.h17227.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039.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) ![Lobby](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/cbe9b050.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) ### 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 (2435) "Staff was amazing! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica CA $95 CA $154 total includes taxes & fees Dec 14 - Dec 15 [](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) ![Restaurant](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/fbec7123.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) ![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 [](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 $261 CA $295 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Chicago-Hotels-The-Publishing-House-Bed-And-Breakfast.h19116049.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) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/w3837h2557x3y3-ae185e7a.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 24 - Dec 25 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Orrington-Evanston.h19722.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5600/5555/213d7224.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) ### 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) "Amazing stay felt right at home staff was very accommodating " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tisha CA $151 CA $170 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Chicago-Hotels-Renaissance-Chicago-North-Shore-Hotel.h5555.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/33cebf5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/1e81a9f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/1f607bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/a16e8e9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 15mins DT | Wicker Park Gem | Sleeps 7 | FreePark [](https://www.expedia.ca/Chicago-Hotels-15mins-DT-Wicker-Park-Gem-Sleeps-7-FreePark.h116934319.Hotel-Information) East Garfield Park CA $66 CA $307 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/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) ![Reception](https://images.trvl-media.com/lodging/97000000/96840000/96832200/96832125/16ec13d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Apartment | Shared kitchen facilities](https://images.trvl-media.com/lodging/97000000/96840000/96832200/96832125/056d59c8.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 (177) "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 Dec 28 - Dec 29 [](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) ![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) ![Reception](https://images.trvl-media.com/lodging/1000000/560000/558000/557992/a2f5c82b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/560000/558000/557992/e25c0e7b.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 $128 CA $145 total includes taxes & fees Dec 18 - Dec 19 [](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=2025-12-27&endDate=2025-12-28®ionId=800024&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top The Loop 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 "Easy and fast " [](https://expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h565746.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in Chicago ](https://www.expedia.ca/5Star-Chicago-Hotels.s50-0-d178248.Travel-Guide-Filter-Hotels) - [Hotels near Art Institute of Chicago ](https://www.expedia.ca/Art-Institute-Of-Chicago-Hotels.0-l6064021-0.Travel-Guide-Filter-Hotels) - [Hotels near Chase Tower ](https://www.expedia.ca/Chase-Tower-Hotels.0-l553248621555594882-0.Travel-Guide-Filter-Hotels) - 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