Title: Book the Best Oakland FAMILY FRIENDLY Hotels from CA $115 - Kid-Friendly Hotels in Oakland, Chicago | Expedia.ca [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)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d6132392.Car-Rental-Guide)[Oakland Vacations](https://expedia.ca/Oakland.d6132392.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 Oakland, Chicago from CA $115 - ![](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 Oakland Family Hotels Tonight [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-12-11&endDate=2025-12-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Our top choices for Oakland family-friendly hotels ![Premium Private Quadruple Room, 4 Twin Beds](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/95c55eda.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/10000000/9420000/9418300/9418281/2aaf07f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/32b602ff.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 (2637) "The room was spotless and the staff where great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $81 CA $119 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/5bec7925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/d37889fe.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e7ca688f.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 (4846) "Great location, comfortable room, and nice staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claudia CA $101 CA $118 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/34f4da65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/a9fdeea6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/6f539c86.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 (3005) "Enjoyed this hotel stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly CA $87 CA $143 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![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) ![Hypo-allergenic bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a68260d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; Latin American cuisine](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/cadeb422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sable at Navy Pier Chicago, Curio Collection by Hilton [](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (2257) "This place was amazing !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jayla Danyell CA $132 CA $202 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/2435ca6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/ec33d4f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/0ea4e737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites by Hilton Chicago Downtown Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information) Downtown Chicago 8.4/10 Very good (2739) "Great food clean room friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARINA CA $108 CA $167 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information) ![Reception hall](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/a08df61e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Magnificent)](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/53a89031.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/2000000/1890000/1880400/1880320/afa1818a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eurostars Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (3144) "Amazing and will be staying again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angie CA $119 CA $140 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/01c93cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/1c7b677d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/832f7b8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palmer House a Hilton Hotel [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) Downtown Chicago 8.4/10 Very good (2135) "Loved and enjoyed our stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luis CA $153 CA $213 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/d5b5d773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/0f103d66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/3b2677cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/5bee96cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown South Loop [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information) Downtown Chicago 8.8/10 Excellent (1753) "Clean and staff was courteous. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) HANNAH CA $98 CA $115 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/7744cb58.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/d34c171a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Suite, 1 King Bed (2 Room)](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/w3837h2561x3y0-7e662cc9.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 (1478) "I really liked this location - we will stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynnsey CA $95 CA $152 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Chicago-Hotels-Claridge-House-Chicago.h22684.Hotel-Information) ![Nightclub](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/0120c0e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/9378ca8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed | View from room](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/3ef6d343.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/db1e81f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Quarters Hotel, Central Loop, Chicago [](https://www.expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h565746.Hotel-Information) Downtown Chicago 8.8/10 Excellent (3298) "Great staff, good location, close to transport and attractions" ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Paul CA $100 CA $117 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h565746.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=2025-12-26&endDate=2025-12-27®ionId=6132392&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Oakland 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 "Great location" [](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.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 hotel in a great city" [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.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 "We loved the hotel, parking was a bit of a ways off." [](https://expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Great room with double bathroom. Executive level with private elevator." [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg) ### LondonHouse Chicago, Curio Collection by Hilton 10/10 Excellent "The hotel was beautiful and staff was friendly. It was close and walking distance to a lot of things. Thank you LondonHouse we enjoyed our stay and hope to return in the near future!" [](https://expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.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 "My 2nd time coming to Chicago from miami love it in Chicago my favorite hotel " [](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 "Overall stay was great! The staff and valet were very polite. My only complaint is there was hair in the shower when we checked in. Cleanliness there could be improved. I just washed it down the drain but it wasn’t pleasant to see. Otherwise, the hotel was very nice, close to many things & valet was quick to return our car to us. I’d stay here again. " [](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "Love this hotel! Friendly and helpful staff, large clean rooms, and great location! " [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.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 "The front desk staff are WONDERFUL !!! the rooms are super comfortable!" 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