Title: Book the Best Winnetka LUXURY Hotels - Upscale Hotels in Winnetka, IL | 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) ![Stinson Memorial Library Anna Illinois Listed on the National Register Funded by Anna businessman Robert Burns Stinson, designed by Walter Burley Griffin who studied under Frank Lloyd Wright.](https://images.trvl-media.com/place/175751/2aaae0bc-b749-4753-83b9-fc353faec42a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/175751/2aaae0bc-b749-4753-83b9-fc353faec42a.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 availability on Winnetka Luxury Hotels Tonight [Mar 19 - Mar 20](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-03-19&endDate=2026-03-20&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Mar 20 - Mar 21](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-03-20&endDate=2026-03-21&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-03-20&endDate=2026-03-22&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-03-27&endDate=2026-03-29&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Winnetka luxury 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) ![Exterior](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/444bc42d.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 (2,412 reviews) "Great spot and view, would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly CA $200 CA $282 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/b9c16475.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) ![Sports facility](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/f4944277.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) ### The Chicago Hotel Collection Ambassador Gold Coast [](https://www.expedia.ca/Chicago-Hotels-The-Chicago-Hotel-Collection-Ambassador-Gold-Coast.h17809.Hotel-Information) Downtown Chicago 8.2/10 Very good (1,310 reviews) "Very beautiful place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) angie CA $165 CA $194 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Chicago-Hotels-The-Chicago-Hotel-Collection-Ambassador-Gold-Coast.h17809.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) ![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) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/8318473d.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 8.6/10 Excellent (2,336 reviews) "We had a great stay and the staff are very friendly and accommodating. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Krista CA $185 CA $251 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Room service - dining](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6d9bcb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/eea57c7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wade [](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) Downtown Chicago 8.4/10 Very good (1,733 reviews) "Loved this hotel, i will be back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shari CA $177 CA $208 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![55-inch LCD TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/bb12c333.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/bf403e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/325d0c28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch LCD TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/2281badb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L7 Chicago by LOTTE [](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information) Downtown Chicago 9.6/10 Exceptional (3,786 reviews) "Amazing hotel-- Loved staying here." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen CA $210 CA $246 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/20000/19300/19215/1e5dfdc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/20000/19300/19215/w3995h2662x0y0-e8059ef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/19300/19215/82978823.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/20000/19300/19215/a00357b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renaissance Chicago Downtown Hotel [](https://www.expedia.ca/Chicago-Hotels-Renaissance-Chicago-Downtown-Hotel.h19215.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (1,000 reviews) "Everything was great - location, service, room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom CA $251 CA $336 total includes taxes & fees Apr 3 - Apr 4 [](https://www.expedia.ca/Chicago-Hotels-Renaissance-Chicago-Downtown-Hotel.h19215.Hotel-Information) ![Indoor wedding](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/3cb3732b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/32068350.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/1000000/20000/17300/17288/aa950453.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/1000000/20000/17300/17288/bebf91fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Swissotel - Chicago [](https://www.expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (3,221 reviews) "Helpful staff, great location with views, restaurant and bar on-site" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Natalie CA $196 CA $278 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/58291697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ccaab668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/f6d9d5c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ecc0a878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sentral Michigan Avenue [](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (1,107 reviews) "The kitchen was great and check-in was easy." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marshal CA $173 CA $244 total includes taxes & fees Apr 6 - Apr 7 [](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/0ec157ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/af0ef9e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/62385a5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/dc5ac11c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric The Loop Chicago [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-The-Loop-Chicago.h9069667.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (2,415 reviews) "this location is safe and convenient-would book here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) eduardo CA $193 CA $261 total includes taxes & fees Mar 20 - Mar 21 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-The-Loop-Chicago.h9069667.Hotel-Information) ![Lounge](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/b59ebdf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cafe](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/b6033176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/95d420ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pendry Chicago [](https://www.expedia.ca/Chicago-Hotels-Pendry-Chicago.h982552.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1,132 reviews) "Great location, clean and very nice restaurant and bar. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) karina CA $260 CA $362 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Chicago-Hotels-Pendry-Chicago.h982552.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=2026-04-02&endDate=2026-04-03®ionId=175751&adults=2&sort=LUXURY&star=40,50&openPlayBack=true) ## Top Winnetka Hotel Reviews ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 6/10 Okay "Older Hilton that is in need of remodeling. Stayed in a ADA room that is advertised as a regular room. " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Courtyard by Marriott Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/7705f099_y.jpg) ### Courtyard by Marriott Chicago Magnificent Mile 10/10 Excellent "The staff were very friendly and helpful." [](https://expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information) ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "I spent 2 nights and everything was great. I'll be back!" [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.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 8/10 Good "Good room lower floor was a little close to the street and a little loud but it’s Chicago so to be expected. Breakfast was good and the room was clean." [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Beautiful property, great resturant on site, an the pool and spa was amazing." [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156_y.jpg) ### The Wade 10/10 Excellent "very clean , loved it" [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/fa2dd97c_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "Everything was nice and clean , great location to walk to everything . " [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f_y.jpg) ### Fairmont Chicago at Millennium Park 10/10 Excellent "There was no kitchen." [](https://expedia.ca/Chicago-Hotels-Fairmont-Chicago-At-Millennium-Park.h15937.Hotel-Information) ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3840h2559x0y3-c577bf94_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "Clean and large room. Reasonable price for early check in. " [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ## Frequently asked questions ### Are you looking for a luxury hotel for your stay in Winnetka? ### When can I expect good weather in Winnetka? ### What's there to see and do in Winnetka? ### How can I get around Winnetka? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [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) - [Business Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Business-Hotel.0-0-d178248-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Chicago ](https://www.expedia.ca/Chicago-Hotels-Couples-Resorts-Hotels.0-0-d178248-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Green Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Green-Sustainable.0-0-d178248-tGreenSustainable.Travel-Guide-Filter-Hotels) - 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