Title: Winnetka Guest Houses from CA $125 | Expedia.ca [Winnetka Travel Guide](https://expedia.ca/Winnetka.dx175751)[Hotels in Winnetka](https://expedia.ca/Winnetka-Hotels.d175751.Travel-Guide-Hotels)[Vacation Rentals in Winnetka](https://expedia.ca/Winnetka-Vacation-Rentals.d175751.Travel-Guide-VacationRentals)[Flights to Winnetka](https://expedia.ca/Cheap-Flights-To-Winnetka.d175751.Travel-Guide-Flights)[Winnetka Car Rentals](https://expedia.ca/Car-Rentals-In-Winnetka.d175751.Car-Rental-Guide)[Winnetka Vacation Packages](https://expedia.ca/Winnetka.d175751.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 prices for these dates Next weekend [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-05-01&endDate=2026-05-03&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-05-29&endDate=2026-05-31&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinnetka-Guest-Houses.d175751-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinnetka-Guest-Houses.d175751-aaGuestHouses.Travel-Guide-Accommodation) ## Top Winnetka Hotel Reviews ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg) ### Hotel Riu Plaza Chicago 8/10 Good "Comfortable Room" [](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![Aloft Chicago Mag Mile](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a_y.jpg) ### Aloft Chicago Mag Mile 8/10 Good "Very live hotel, nice staff and clean. " [](https://expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg) ### Hotel Felix River North/Magnificent Mile 8/10 Good "A quiet and comfortable place" [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Location was great. Valet parking was very accommodating-- extremely helpful" [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/5bec7925_y.jpg) ### River Hotel 10/10 Excellent "Clean room as always Accessible to all main spots in Chicago " [](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/a48bf16b_y.jpg) ### Hilton Chicago O'Hare Airport 10/10 Excellent "I think you took advantage of people needing a place to stay when their flight was cancelled. The price was very inflated but we had very little choice about where we could stay. " [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Great experience " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg) ### DoubleTree by Hilton Chicago - Magnificent Mile 10/10 Excellent "Goods " [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![The Chicago Hotel Collection Ambassador Gold Coast](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/b9c16475_y.jpg) ### The Chicago Hotel Collection Ambassador Gold Coast 4/10 Poor "This was such a disappointing and underwhelming stay. There is zero soundproofing in the rooms, (constant door closing can be heard even over my white noise), housekeeping knocked at 8:20am to assess whether we were still in the room and my daughter was still sleeping, poor internet (WiFi was temperamental and TV was constantly losing signal), the terrace was closed/doors locked, pillows are thin and useless, beds are low to the ground, the carpet is stained and dingy, and I had to ask the front desk twice to review my profile bc I had been charged twice (was resolved). The food is such a loss here. If you’ve ever had food at a bowling alley, this is exactly what the line of food tastes like: I ordered beef empanadas and the margheritia pizza. The pizza tasted previously frozen and the empanadas give me Dollar General frozen food. Thank goodness I paid for “room only” and not the food/beverage package. The strong wins: location, and the bar scene/bartender. Valet was also exceptional. Only reason I didn’t give it 1 star. Do not recommend. The pictures do it way more justice than it deserves. If you’re seeking luxury, this is not it. And perhaps I was booked in a “cheap”/non-upgraded room, but this is not worth it." [](https://expedia.ca/Chicago-Hotels-The-Chicago-Hotel-Collection-Ambassador-Gold-Coast.h17809.Hotel-Information) ## Find out more about Winnetka ## Winnetka Guest Houses information | Number of reviews | 148 | | ----------------- | -------------- | | Accommodation | 6 Guest Houses | | Lowest Price | CA $125 | | Highest Price | CA $194 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [5 Star Hotels in Glenview ](https://www.expedia.ca/5Star-Glenview-Hotels.s50-0-d8006.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Gross Point ](https://www.expedia.ca/5Star-Gross-Point-Chicago-Hotels.s50-n6132100-0.Travel-Guide-Filter-Hotels) - [Hotels near Baha'i House of Worship ](https://www.expedia.ca/Bahai-House-Of-Worship-Hotels.0-l6152644-0.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Botanic Garden ](https://www.expedia.ca/Chicago-Botanic-Garden-Hotels.0-l6064029-0.Travel-Guide-Filter-Hotels) - [Chicago Hotels ](https://www.expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels) - 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