Title: The Best 5 Star Hotels in Winnetka, IL from $151 | Expedia.com [Winnetka Travel Guide](https://expedia.com/Winnetka.dx175751)[Hotels in Winnetka](https://expedia.com/Winnetka-Hotels.d175751.Travel-Guide-Hotels)[Vacation Rentals in Winnetka](https://expedia.com/Winnetka-Vacation-Rentals.d175751.Travel-Guide-VacationRentals)[Flights to Winnetka](https://expedia.com/Cheap-Flights-To-Winnetka.d175751.Travel-Guide-Flights)[Things to do in Winnetka](https://expedia.com/Things-To-Do-In-Winnetka.d175751.Travel-Guide-Activities)[Car Rentals in Winnetka](https://expedia.com/Car-Rentals-In-Winnetka.d175751.Car-Rental-Guide)[Winnetka Vacation Packages](https://expedia.com/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__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](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 5 Star Hotels Tonight [Mar 13 - Mar 14](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-03-13&endDate=2026-03-14&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 14 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-03-14&endDate=2026-03-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-03-13&endDate=2026-03-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-03-20&endDate=2026-03-22&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winnetka 5-star hotels ![Lobby](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/a75a4abb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, hot tub, steam room, body treatments](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/af38c666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, Mediterranean cuisine](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/71f6a2f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/0ab012f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Langham, Chicago [](https://www.expedia.com/Chicago-Hotels-The-Langham.h6309326.Hotel-Information) Downtown Chicago 9.8/10 Exceptional (1,000 reviews) "Great Hotel on all levels" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Demetrios $435 nightly $511 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-The-Langham.h6309326.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/e294b3a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/bbac06a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/5616df34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Peninsula Chicago [](https://www.expedia.com/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information) Downtown Chicago 9.8/10 Exceptional (1,001 reviews) "The spa was relaxing and the staff was so kind." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gordon $525 nightly $616 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information) ![Suite, 2 Bedrooms, Terrace (Lakeshore) | Lake view](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/e5b56b9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/f0e0ee26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/1e19db6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/7da48e89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Hotel Chicago [](https://www.expedia.com/Chicago-Hotels-Four-Seasons-Hotel-Chicago.h25748.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1,001 reviews) "Staff is incredible. Bartenders in lobby bar are phenomenal!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim $395 nightly $464 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-Four-Seasons-Hotel-Chicago.h25748.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/c665b589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/c35e7743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trump International Hotel & Tower Chicago [](https://www.expedia.com/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1,847 reviews) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark $371 nightly $436 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information) ![Breakfast, lunch, dinner served; American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c8149674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Terrace (Water Tower) | Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (LAKE MICHIGAN SUITE) | View from room](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/ef2f5d42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/3c600fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Park Hyatt Chicago [](https://www.expedia.com/Chicago-Hotels-Park-Hyatt-Chicago.h20695.Hotel-Information) Downtown Chicago 9.6/10 Exceptional (1,001 reviews) "Everything was great… but the staff was absolutely amazing! Thank you for taking such great care of us. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gaybrielle $412 nightly $484 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-Park-Hyatt-Chicago.h20695.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1ede47da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/c47ab94b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pet-friendly](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/c2c59838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/dfd1e89b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waldorf Astoria Chicago [](https://www.expedia.com/Chicago-Hotels-Waldorf-Astoria-Chicago.h2717582.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1,000 reviews) "Staff, room and accommodations were superb! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William $406 nightly $476 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-Waldorf-Astoria-Chicago.h2717582.Hotel-Information) ![Designer toiletries, hair dryer, bathrobes, towels](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/ccd16d9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/8f021abe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/fbfdc974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/70844348.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nobu Hotel Chicago [](https://www.expedia.com/Chicago-Hotels-Nobu-Hotel-Chicago.h36475533.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (800 reviews) "Close to metro and downtown, good restaurants near by " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Douglas $375 nightly $440 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-Nobu-Hotel-Chicago.h36475533.Hotel-Information) ![Cafe](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/29a217ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/w4000h2662x0y0-6ee2614f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/eab0af51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/w4000h2663x0y0-c4579ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton, Chicago [](https://www.expedia.com/Chicago-Hotels-The-Ritz-Carlton.h14447.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (1,002 reviews) "great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Curtis $396 nightly $465 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-The-Ritz-Carlton.h14447.Hotel-Information) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/0d225744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/1e67e2bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/ff21d1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/w4000h2645x0y22-fdcb2993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The St. Regis Chicago [](https://www.expedia.com/Chicago-Hotels-The-St-Regis-Chicago.h91138950.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (102 reviews) "The staff was exceptional, and the amenities, coupled with the stunning views of the river or city, make this a fantastic choice. The on-site restaurants provide convenient access to food. My only minor complaint is the absence of a mini fridge in the room to keep some drinks cool. I would definitely be booking again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eddie $446 nightly $524 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Chicago-Hotels-The-St-Regis-Chicago.h91138950.Hotel-Information) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Winnetka-Hotels.s50-0-d175751.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Winnetka-Hotels.s50-0-d175751.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winnetka. ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St Chicago IL $129 nightly $151 total Mar 15 - Mar 16 Total with taxes and fees 8.6/10 Excellent! (5,735 reviews) [](https://expedia.com/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/a48bf16b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hilton Chicago O'Hare Airport O'Hare International Airport Chicago IL $196 nightly $230 total Apr 3 - Apr 4 Total with taxes and fees 8.4/10 Very Good! (2,217 reviews) [](https://expedia.com/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.Hotel-Information) ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hotel Riu Plaza Chicago 150 East Ontario Street Chicago IL $156 nightly $183 total Mar 30 - Mar 31 Total with taxes and fees 9.4/10 Exceptional! (3,522 reviews) [](https://expedia.com/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) Still don't see what you're looking for? [See all properties in Winnetka.](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F14%2F2026&endDate=3%2F15%2F2026®ionId=175751&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F14%2F2026&endDate=3%2F15%2F2026®ionId=175751&star=50&star=50&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F14%2F2026&endDate=3%2F15%2F2026®ionId=175751&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F14%2F2026&endDate=3%2F15%2F2026®ionId=175751&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F14%2F2026&endDate=3%2F15%2F2026®ionId=175751&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F14%2F2026&endDate=3%2F15%2F2026®ionId=175751&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Winnetka Elegant North Shore homes line the streets near Lake Michigan beaches where locals picnic during summer festivals. Explore the historic Crow Island School's architecture or catch a show at the Winnetka Community House theater. [See all hotels in Winnetka](https://www.expedia.com/Hotel-Search?startDate=2026-03-27&endDate=2026-03-28&adults=2®ionId=175751) ![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=899&h=599&p=1&q=high) ## Top Winnetka Hotel Reviews ## Find out more about Winnetka There's nothing wrong with enjoying the finer things in life. Indulge your every whim on your impending break. There's no reason to delay a getaway to Winnetka any longer. You'll join the multitudes of vacationers who have made Winnetka so fashionable in the last few seasons. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Reserve one of our 5-star hotels in Winnetka and indulge in the finer things in life for a while. ### Get a Great Deal on 5-Star Hotels in Winnetka You'll have a wonderful time at one of these 5-star hotels. Excellent service, delicious meals, and attentive guest service are all at your fingertips. You're sure to find exactly the accommodation you need. You can also look forward to an outstanding experience and fantastic customer care, so get ready for a wonderful adventure. What creature comforts do you want in your lodging? A concierge to help you suggest the next attraction to visit? A rejuvenating facial treatment to help your cares fall away? Comfortable beds, piping hot coffees, and even spectacular views...these hotels will astonish you. Want to see for yourself? Explore our listings and pick the perfect accommodation for your needs. Can't wait to get outside? We've got you covered. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Winnetka are the perfect place to relax after a busy day. ### Your Getaway Starts Today The results are in, and Winnetka 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. Your great getaway is just a mouse-click away. Select one of our Winnetka 5-star hotels today and relax in luxe surroundings tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Winnetka? > - Search for the lowest price per night from $151 ### What makes a hotel 5 stars in Winnetka? ### Are there any 5-star all-inclusive resorts in Winnetka? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Chicago Hotels ](https://www.expedia.com/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Hotels near Downtown Chicago ](https://www.expedia.com/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Hotels near Home Alone House ](https://www.expedia.com/Home-Alone-House-Hotels.0-l553248635997949865-0.Travel-Guide-Filter-Hotels) - [Hotels near Winnetka Station ](https://www.expedia.com/Winnetka-Station-Hotels.d6214780.Travel-Guide-Hotels) - [Hotels near Chocolate Box ](https://www.expedia.com/Chocolate-Box-Hotels.0-l553248621532658670-0.Travel-Guide-Filter-Hotels) - 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