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://a.travel-assets.com/travel-assets-manager/bex-affinities/bar.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Bar in Westchester, IL from CA $231 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/55a8ba7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a9c979ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago 9.4/10 Exceptional (2159) "Great hotel " CA $266 CA $353 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/2d37be79.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/7744cb58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Claridge House Downtown Chicago 9.0/10 Wonderful (1377) "Wonderful Stay!" CA $168 CA $239 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Chicago-Hotels-Claridge-House.h22684.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/f0cafd98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/54e0cfd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/b9c16475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/4acc297e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Chicago Hotel Collection Ambassador Gold Coast Downtown Chicago 8.2/10 Very good (1151) "Room and breakfast fantastic!" CA $219 CA $257 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Chicago-Hotels-The-Chicago-Hotel-Collection-Ambassador-Gold-Coast.h17809.Hotel-Information) ![3 bars/lounges, piano bar](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/d06b01bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/9752c1a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 1 King Bed](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/36d2e00e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/w1101h1283x0y1-ef09926c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hoxton Chicago Downtown Chicago 9.0/10 Wonderful (1000) "Beautiful hotel in a great location " CA $305 CA $358 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chicago-Hotels-The-Hoxton-Chicago.h34761378.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) ![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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/ac302b90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/f00e51d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Millennium Knickerbocker Chicago Downtown Chicago 8.6/10 Excellent (1967) "Great hotel, perfectly located. " CA $184 CA $249 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Chicago-Hotels-Millennium-Knickerbocker-Chicago.h15087.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/w2559h3837x0y3-191558cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/w2560h3837x0y3-423017d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/95b10764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/bda30653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Thompson Chicago, by Hyatt Downtown Chicago 9.2/10 Wonderful (1245) "Expensive, but comfortable and in a great location " CA $231 CA $313 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Chicago-Hotels-Thompson-Chicago.h26076.Hotel-Information) ![City view from property](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/d1cc0289.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/7b0fa7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/1bc6749f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/1df0c87e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt House Chicago West Loop Downtown Chicago 8.8/10 Excellent (1044) "Great location near lots of restaurants. " CA $272 CA $319 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-House-Chicago-West-Loop.h35834237.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/c5cac7c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/05f95ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves breakfast, lunch, and dinner](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/b0f5bd1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silversmith Hotel Chicago Downtown Downtown Chicago 9.4/10 Exceptional (1992) "Excellent hotel, staff, location. " CA $180 CA $252 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.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) ![Front of property](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/43039f7e.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) ![Standard Room](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/22cb8b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Warwick Allerton - Chicago Downtown Chicago 8.4/10 Very good (2893) "Great location, friendly staff." CA $162 CA $231 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/ab309a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/36960d65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/df696474.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/19390ef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Godfrey Hotel Chicago Downtown Chicago 8.6/10 Excellent (1880) "Great hotel" CA $212 CA $282 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-The-Godfrey-Hotel-Chicago.h7063210.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=2025-10-16&endDate=2025-10-17®ionId=7758&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Westchester Hotel Reviews ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Top Lage, sehr zentral" [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.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 "Staff was excellent. Decor was very elegant and classy. Enjoyed my two nights here." [](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 "Great location to and walking to riverwalk, millennium park. Metro is right outside the front door. " [](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 staff, everything in walking distance from hotel. Would stay here again. " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "someone smoked as the mattress smelled of smoke. luggage rack is broken" [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.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 "Outstanding place to stay in downtown Chicago " [](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "Rooms were clean and staff were always happy to help " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Palmer House a Hilton Hotel](//images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Great property with great staff and amenities. " [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "We had a fantastic stay at the Embassy Suites by Hilton Chicago Downtown River North. Our suite was impressively clean and offered plenty of space to spread out, which made it especially comfortable for a multi-day visit. Everything felt well maintained and tidy, which gave us peace of mind right from the start. The location was another highlight. Being in River North meant we were close to great restaurants, shopping, and attractions, and having the subway nearby made getting around the city easy and convenient. It was the perfect base for exploring Chicago. Breakfast was outstanding and far above the standard hotel fare. There were lots of options to choose from, including fresh fruit, pastries, hot items, and the standout feature—a station for custom-made omelets. It was a great way to start each day, and the variety meant there was something for everyone. Overall, Embassy Suites River North checked all the boxes: clean, spacious, well-located, and with excellent breakfast to top it off. We would happily stay here again on our next trip to Chicago." [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.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 10 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. [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. [Hilton Chicago O'Hare Airport](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and breakfast. [CitizenM Chicago Downtown](https://www.expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and room service. ### 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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