Title: Book the Best The Loop WINERY Hotels in 2025 | 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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543387-chicago.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in The Loop, IL ![](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 [Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=800024&startDate=2025-10-28&endDate=2025-10-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=800024&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=800024&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=800024&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top The Loop 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) ![Interior entrance](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/9097f753.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) ![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 Downtown Chicago 8.2/10 Very good (2314) "Amazing stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Triston CA $100 CA $160 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/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) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/b6152ff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 2 Double Beds, Non Smoking, Refrigerator (with Sofabed)](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/aeb6fede.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) ### Best Western River North Hotel Downtown Chicago 7.8/10 Good (1010) "Great stay" ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Bart CA $141 CA $166 total includes taxes & fees Nov 9 - Nov 10 [](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) ![Property entrance](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/6cf646d9.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) ![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 Downtown Chicago 9.8/10 Exceptional (186) "Wonderful staff, beautiful hotel and great breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Veronica CA $281 CA $318 total includes taxes & fees Nov 16 - Nov 17 [](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) ![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) ![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) ![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) ### Renaissance Chicago North Shore Hotel Northbrook 8.2/10 Very good (1008) "Every thing was good " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica CA $165 CA $186 total includes taxes & fees Nov 14 - Nov 15 [](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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/57f153c2.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) ### Hilton Orrington / Evanston Downtown Evanston 7.6/10 Good (1001) "Good stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LiHui CA $201 CA $230 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Orrington-Evanston.h19722.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) ![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) ![Interior](https://images.trvl-media.com/lodging/117000000/116940000/116934400/116934319/d19de994.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) ### 15mins DT | Wicker Park Gem | Sleeps 7 | FreePark East Garfield Park CA $84 CA $345 total includes taxes & fees Nov 4 - Nov 5 [](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) ![Deluxe Studio | Living area](https://images.trvl-media.com/lodging/97000000/96840000/96832200/96832125/6e62c16d.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 )](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 (167) "It was cheap, friendly, and even the other guests were accommodating!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cara CA $50 CA $133 total includes taxes & fees Oct 29 - Oct 30 [](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, Non Smoking | Bathroom](https://images.trvl-media.com/lodging/1000000/560000/558000/557992/a9cb9b76.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) ### Four Points by Sheraton Mt Prospect O'Hare Mount Prospect 8.0/10 Very good (533) "Great place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MOHAMMED CA $154 CA $174 total includes taxes & fees Nov 23 - Nov 24 [](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=2025-11-11&endDate=2025-11-12®ionId=800024&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top The Loop Hotel Reviews ## 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) - [Aparthotels in Chicago](https://www.expedia.ca/Chicago-Apart-Hotels.d178248-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Chicago](https://www.expedia.ca/Chicago-Bed-And-Breakfast.d178248-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hostels in Chicago](https://www.expedia.ca/Chicago-Hostels.d178248-aaHostels.Travel-Guide-Accommodation) - 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