Title: Book the Best Westchester FAMILY FRIENDLY Hotels from CA $109 - 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) ![Schiller Woods view in Chicago of Illinois](https://images.trvl-media.com/place/7758/5dc6d33e-4d46-4f37-9026-58124815a2a3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Family Hotels in Westchester, IL from CA $109 - ![](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 Family Hotels Tonight [Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Dec 20 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2025-12-20&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Our top choices for Westchester family-friendly hotels ![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) ![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c.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) ![Reception](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/5132819a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freehand Chicago [](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) Downtown Chicago 8.0/10 Very good (2651) "It's an excellent place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose CA $72 CA $109 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.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) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/ccacdd84.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/023ff9a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Warwick Allerton - Chicago [](https://www.expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) Downtown Chicago 8.4/10 Very good (2999) "Enjoyed this hotel stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly CA $86 CA $141 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Kitchenette (One Room)](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/61142942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/c5202ed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/74cf409f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Quarters Hotel Wacker at Michigan, Chicago [](https://www.expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information) Downtown Chicago 8.8/10 Excellent (1996) "A good place for stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julio CA $105 CA $123 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/20000/16800/16741/04763dda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional Room, 1 King Bed | Reception](https://images.trvl-media.com/lodging/1000000/20000/16800/16741/abc6bdc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16800/16741/3923595e.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 [](https://www.expedia.ca/Chicago-Hotels-Four-Points-By-Sheraton-Chicago-WestchesterOak-Brook.h16741.Hotel-Information) Westchester 8.6/10 Excellent (1003) "Thanks, great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $128 CA $143 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Chicago-Hotels-Four-Points-By-Sheraton-Chicago-WestchesterOak-Brook.h16741.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e85c42c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e50ef89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/511c43ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Hotel [](https://www.expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) Downtown Chicago 8.8/10 Excellent (4837) "Great location, comfortable room, and nice staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claudia CA $106 CA $125 total includes taxes & fees Jan 18 - Jan 19, 2026 [](https://www.expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/461957e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/19cc7c07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Corner](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/cc228cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/186b641d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Chicago Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (1053) "Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hannah CA $135 CA $199 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/w3837h2556x3y3-aad44a42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/968cca43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fusion cuisine](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/e4e05f11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch LCD TV with cable channels, TV, tablet](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/bd401f3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Claridge House Chicago, Tapestry Collection by Hilton [](https://www.expedia.ca/Chicago-Hotels-Claridge-House-Chicago.h22684.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (1482) "Nice stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $89 CA $145 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Chicago-Hotels-Claridge-House-Chicago.h22684.Hotel-Information) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e43f096f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, City View | Living area](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/cc919354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Congress Plaza Hotel [](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) Downtown Chicago 8.0/10 Very good (9674) "Wonderful stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zach CA $129 CA $152 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b5bf3aa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b812d0f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/bbeef356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago [](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) Downtown Chicago 8.4/10 Very good (2383) "Great amenities and staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward J CA $157 CA $225 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b1113923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b131add8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/8e39b688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/d7ae47e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Chicago - Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) Downtown Chicago 8.8/10 Excellent (2191) "Very friendly staff, clean rooms, the location is amazing and near of everything " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarwat CA $123 CA $145 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.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=2026-01-02&endDate=2026-01-03®ionId=7758&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Westchester Hotel Reviews ![Crowne Plaza Chicago West Loop by IHG](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg) ### Crowne Plaza Chicago West Loop by IHG 10/10 Excellent "The room was clean, but basic. The restaurant and food was great. The staff were very helpful and most were friendly. The location was excellent, a safe neighborhood with many restaurants and nice stores including Whole Foods in short walking distance. I'd stay here again. Try eating at Meli and Nancy's Pizza." [](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information) ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "From beginning to end it was awesome.....Except for parking it was horrible I got lost for about 30 mins trying to find my rental....BUT the 🏨 employees were all very helpful and we found it in no time after that ❤️.....The 🏨 was awesome, views ❤️ and the vibe was on point everything was at a walking distance 🥰.... Beautiful city day or 🌃 please preserve it as much as you can. I'm from California and greatly appreciate the hospitality ❤️ 🙏" [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg) ### Eurostars Magnificent Mile 10/10 Excellent "Loved this hotel. The only thing I disliked was not having a microwave in my room. I ate out daily but sometimes did not finish my food and would have to throw it out due to not having anything to reheat it. The fridge was so stocked with their items that there was barely room to put your own stuff in there. " [](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "free alc beverages at night, huge breakfast " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg) ### Club Quarters Hotel Wacker at Michigan, Chicago 10/10 Excellent "Easy check in/check out process. Staff was very friendly and helpful. Hotel is conveniently located for walking to shopping, food, and sightseeing " [](https://expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information) ![Holiday Inn Chicago Dwtn - The Mart by IHG](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344_y.jpg) ### Holiday Inn Chicago Dwtn - The Mart by IHG 10/10 Excellent "Excellent room, staff & amenities. Everyone was very helpful." [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Very comfortable quit clean hotel very convenient and the staff was professional and very pleasant I highly recommend this property " [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![InterContinental Chicago Magnificent Mile by IHG](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "Good" [](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Great location! Nice view, good staff " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ## Frequently asked questions ### What's Westchester like for family-friendly vacations? ### When's the best time to book a family-friendly vacation in Westchester? ### What's there to see and do with your family in Westchester? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Farmstay in Bellwood ](https://www.expedia.ca/Bellwood-Agritourism.d6132079-aaAgritourism.Travel-Guide-Accommodation) - [B&B in Bellwood ](https://www.expedia.ca/Bellwood-Bed-And-Breakfast.d6132079-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Golf Hotels in Bellwood ](https://www.expedia.ca/Bellwood-Hotels-Golf-Hotel.0-0-d6132079-tGolfHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Bellwood ](https://www.expedia.ca/Bellwood-Hotels-Spa-Hotel.0-0-d6132079-tSpaHotel.Travel-Guide-Filter-Hotels) - [Bellwood Hotels ](https://www.expedia.ca/Bellwood-Hotels.d6132079.Travel-Guide-Hotels) - 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