Title: Book the Best Hotels with BARS in Westchester in 2025 | Expedia.ca [Hotels in Westchester](https://expedia.ca/Westchester-Hotels.d7758.Travel-Guide-Hotels)[Vacation Rentals in Westchester](https://expedia.ca/Westchester-Vacation-Rentals.d7758.Travel-Guide-VacationRentals)[Westchester Car Rentals](https://expedia.ca/Car-Rentals-In-Westchester.d7758.Car-Rental-Guide)[Westchester Vacation Packages](https://expedia.ca/Westchester.d7758.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Bar in Westchester, IL from CA $151 ![](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 Westchester Hotels with Bar ## Top Westchester Hotels with Bar ![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/5132819a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/cb4330d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/c14e1876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freehand Chicago Downtown Chicago 8.0/10 Very good (2472) "Great place" CA $107 CA $151 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/cc779b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/f5c52beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/c0ded825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Riu Plaza Chicago Downtown Chicago 9.4/10 Exceptional (2601) "Great place to stay " CA $199 CA $273 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/023ff9a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/22cb8b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/ccacdd84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Warwick Allerton - Chicago Downtown Chicago 8.4/10 Very good (2926) "The lodging was super nice." CA $129 CA $193 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/eac67ea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![City view](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/340ea126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/3912d77d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/2c655ed8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Millennium Knickerbocker Chicago Downtown Chicago 8.6/10 Excellent (1992) "We have stayed here several times and love the hotel and location." CA $139 CA $196 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Chicago-Hotels-Millennium-Knickerbocker-Chicago.h15087.Hotel-Information) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/fd235ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/c8177aa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/8750140b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Whitehall Hotel, BW Premier Collection Downtown Chicago 8.2/10 Very good (3659) "Great location , good breakfast" CA $138 CA $162 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/5ea33759.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/7744cb58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/880fa2cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/bab7a943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Claridge House Downtown Chicago 9.0/10 Wonderful (1417) "Wonderful Stay!" CA $116 CA $178 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-Claridge-House.h22684.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/6b27f192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/ddbd86a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/dd081548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, free cribs/infant beds](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/64c4029a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### voco Chicago Downtown - Riverwalk by IHG Downtown Chicago 8.8/10 Excellent (3211) "Great stay " CA $224 CA $262 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information) ![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/943262bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/e47956bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/c042bdff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wade Downtown Chicago 8.4/10 Very good (1369) "Great place to stay" CA $190 CA $223 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, City View | View from room](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/c06f4b61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 20.00 per person)](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/8967eebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/bb272e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Chicago Downtown Downtown Chicago 9.2/10 Wonderful (3951) "Great place to stay. " CA $184 CA $216 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/56c2d84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/50be090a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chicago Mag Mile Downtown Chicago 8.6/10 Excellent (2867) "Had a great stay!" CA $194 CA $228 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.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=2025-10-29&endDate=2025-10-30®ionId=7758&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Westchester Hotel Reviews ![DoubleTree by Hilton Chicago - Magnificent Mile](//images.trvl-media.com/lodging/1000000/30000/21200/21152/b1113923_y.jpg) ### DoubleTree by Hilton Chicago - Magnificent Mile 10/10 Excellent "This was perfect for Chicago Marathon. Good proximity to start and finish (about a mile) and was excellent location for spectating. " [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "Breakfast was great! " [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](//images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile 10/10 Excellent "Excellent location for visiting Chicago, near major attractions, walking distance to mig mile and Chicago river. Subway station is beside the hotel. Many restaurants are around. Hotel is a little old but condition is good and the price is reasonable. Staffs are very friendly. " [](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Clean rooms, great service." [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![InterContinental Chicago Magnificent Mile by IHG](//images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "The bell hops were awesome!! If i needed to know anything, all i had to do was ask them. " [](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![The Royal Sonesta Chicago Downtown](//images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "This was the best hotel I ever stayed at! I did not want to leave. It was very clean and the cleaning staff was attentive and thorough. The staff at the desk were friendly and knowledgeable, and never acted disgruntled or impatient. The bellhops were excellent and trustworthy and anticipated our needs. The hotel was just beautiful and clean in the lobby with boutique atmosphere and art. The room was spacious with comfortable bed and furnishings. The coffee was excellent and the bathroom felt luxurious. We just loved everything! The restaurant food was great quality and not overpriced. And, our location downtown couldn’t be better, near Riverwalk and Michigan Avenue. We thoroughly enjoyed our stay. Thank you, Sonesta!" [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Clean.Comfortable beds. Great location .Includes a great breakfast." [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "All the staff had great energy and were very helpful. Nice bar/lounge area and cozy space. I had a private room and though it wasn’t huge, it was exactly what we needed for our staycation." [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "Everything was great. It was awesome being back in Chicago again. " [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Westchester? > Though you might not find a hotel in Westchester well-known for its bar, you will find 11 properties to choose from, some of which will have an onsite bar where you can unwind with an evening cocktail after sightseeing. While you're in the area, consider a visit to Wrigley Field and Michigan Avenue. ### What are the best hotels with bars in Westchester? > Here are some favorite hotels with bars in and around Westchester: [Congress Plaza Hotel](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information): Hotel with 2 restaurants. Enjoy the 2 bars, free WiFi, and breakfast. [Freehand Chicago](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and room service. [Embassy Suites by Hilton Chicago Downtown River North](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information): Hotel with restaurant. Enjoy the bar, free breakfast, and WiFi. [Hilton Chicago/Magnificent Mile Suites](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and room service. [Hilton Garden Inn Chicago Downtown/Magnificent Mile](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information): Hotel with 2 restaurants. Enjoy the bar, free WiFi, and breakfast. ### What is there to do in Westchester? > Absorb the local culture by visiting Wrigley Field, United Center, and Soldier Field, then unwind with a refreshing drink. Other places to see in the area include Michigan Avenue and Navy Pier. Westchester is known for its shops and restaurants. ### When is the best time to visit Westchester? > Visiting local bars in Westchester is more fun in good weather. These rainfall averages and temperatures can help you choose the best time for bar hopping. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Westchester are January, November, February, and December, with each month seeing an average of 5 inches of snowfall. ### How can I get to Westchester and around the area? > You might want to make the most of these transportation choices in and around Westchester: Fly into Chicago Midway Airport (MDW), which is located 8.4 mi (13.4 km) from the city center. You can also search for flights into Chicago O'Hare Intl. Airport (ORD), which is 8.9 mi (14.3 km) away. 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