Title: Book the Best Westchester FAMILY FRIENDLY Hotels from CA $140 - Kid-Friendly Hotels in Westchester, IL | 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/family_friendly.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Family Hotels in Westchester, IL from CA $140 ![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 Family Hotels Tonight [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2025-10-02&endDate=2025-10-03&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2025-10-03&endDate=2025-10-04&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2025-10-03&endDate=2025-10-05&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2025-10-10&endDate=2025-10-12&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Westchester Family Hotels ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.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) ![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) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.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 (2185) "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) ![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 (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/d35b9e24.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 (1150) "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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/20000/16800/16741/90bd9308.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional Room, 1 King Bed, Non Smoking | Reception](https://images.trvl-media.com/lodging/1000000/20000/16800/16741/abc6bdc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/16800/16741/ffc69bef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/20000/16800/16741/2f64979b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Points by Sheraton Chicago Westchester/Oak Brook Westchester 8.6/10 Excellent (1000) "Clean room, friendly staff" CA $125 CA $140 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Chicago-Hotels-Four-Points-By-Sheraton-Chicago-WestchesterOak-Brook.h16741.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/b80be72b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w905h683x59y0-8cb3eda8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w905h683x60y0-4a286511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w906h683x59y0-ad8ac03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago! Westchester 9.8/10 Exceptional (19) "Great place Great location " CA $241 CA $589 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-PROMO-10WEEKLY-12-MONTHLY-DISCJacuzzi.h95134539.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) ![Exterior](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/w1101h1283x0y1-ef09926c.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) ### 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) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/7000000/6440000/6435600/6435554/a8543b27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/7000000/6440000/6435600/6435554/66e1ac0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed | View from room](https://images.trvl-media.com/lodging/7000000/6440000/6435600/6435554/cd8ce5ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/7000000/6440000/6435600/6435554/48ddc204.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ohio House Motel Downtown Chicago 9.0/10 Wonderful (1031) "Awesome place to stay. " CA $168 CA $197 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Chicago-Hotels-Ohio-House-Motel.h6435554.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/w3837h2557x3y3-ef0f356b.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/w2560h3837x0y3-423017d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Thompson Chicago, by Hyatt Downtown Chicago 9.2/10 Wonderful (1244) "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) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/197000/196959/b675990c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, laptop workspace, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/200000/197000/196959/1daf4199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/200000/197000/196959/9b08c1bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, laptop workspace, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/200000/197000/196959/0bc5a1e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Downtown Chicago Downtown Chicago 7.2/10 Good (2367) "Comfortable bed, bright room, good shower, very accessible location." CA $165 CA $193 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Travelodge-By-Wyndham-Downtown-Chicago.h196959.Hotel-Information) ![Premium Private Quadruple Room, 4 Twin Beds](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/8684edc8.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) ![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/2aaf07f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freehand Chicago Downtown Chicago 8.0/10 Very good (2422) "Great walkable location to all the sights! " CA $138 CA $227 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.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&travelerType=family_friendly&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 ### What's Westchester like for family-friendly vacations? > You might want to consider the welcoming destination of Westchester if you've been thinking about a trip for the whole family. The golfing, basketball games, and restaurants are just some of the things that make this an attractive family vacation spot. Arrange a flight into Chicago Midway Airport (MDW), which is the closest airport, or Chicago O'Hare Intl. Airport (ORD), which is located 8.9 mi (14.3 km) from the city center. ### When's the best time to book a family-friendly vacation in Westchester? > 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. ### What's there to see and do with your family in Westchester? > While you and your family are visiting Westchester, you might want to check out some kid-friendly attractions such as Wrigley Field, Michigan Avenue, and Navy Pier. 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