Title: 5 Stars Hotels in Crestwood, Chicago from CA $192 - Find Cheap Crestwood Hotels With 5 Stars | Expedia.ca [Crestwood Travel Guide](https://expedia.ca/Crestwood.dx6960)[Hotels in Crestwood](https://expedia.ca/Crestwood-Hotels.d6960.Travel-Guide-Hotels)[Vacation Rentals in Crestwood](https://expedia.ca/Crestwood-Vacation-Rentals.d6960.Travel-Guide-VacationRentals)[Flights to Crestwood](https://expedia.ca/Cheap-Flights-To-Crestwood.d6960.Travel-Guide-Flights)[Things to do in Crestwood](https://expedia.ca/Things-To-Do-In-Crestwood.d6960.Travel-Guide-Activities)[Crestwood Car Rentals](https://expedia.ca/Car-Rentals-In-Crestwood.d6960.Car-Rental-Guide)[Crestwood Vacation Packages](https://expedia.ca/Crestwood.d6960.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Crestwood, Chicago from CA $192 ![](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 Crestwood 5 Star Hotels Tonight [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6960&startDate=2025-10-25&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=6960&startDate=2025-10-26&endDate=2025-10-27&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6960&startDate=2025-10-31&endDate=2025-11-02&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6960&startDate=2025-11-07&endDate=2025-11-09&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Crestwood 5 Star Hotels ![Lobby](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Club Suite, 1 Bedroom, Lake View](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/9a653c17.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) ![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) ### The Langham, Chicago Downtown Chicago 9.8/10 Exceptional (1016) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shawn CA $700 CA $822 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-The-Langham.h6309326.Hotel-Information) ![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) ![Body treatments, body wraps, body scrubs, facials](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/743bf216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02.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) ### Trump International Hotel & Tower Chicago Downtown Chicago 9.4/10 Exceptional (1762) "Very accommodating and friendly staff, brilliant location" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Aaron CA $604 CA $709 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/7da48e89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, minibar, in-room safe](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/56d62feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/d00895ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/fc796025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Hotel Chicago Downtown Chicago 9.4/10 Exceptional (999) "Amazing hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $686 CA $805 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Four-Seasons-Hotel-Chicago.h25748.Hotel-Information) ![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) ![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) ![Ballroom](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/5616df34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/acbf2aab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Peninsula Chicago Downtown Chicago 9.8/10 Exceptional (1021) "Great weekend get away" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) craig CA $805 CA $945 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a.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) ![Bar (on property)](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/5001f31e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/9baa79de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waldorf Astoria Chicago Downtown Chicago 9.4/10 Exceptional (1001) "Simply love this hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) laura CA $660 CA $775 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Waldorf-Astoria-Chicago.h2717582.Hotel-Information) ![Indoor pool, open 6:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/486e1134.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/37000000/36480000/36475600/36475533/82915bb7.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) ![Designer toiletries, hair dryer, bathrobes, towels](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/ab9e9616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nobu Hotel Chicago Downtown Chicago 9.4/10 Exceptional (739) "Great location, amenities and staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas CA $485 CA $569 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Nobu-Hotel-Chicago.h36475533.Hotel-Information) ![Suite, Terrace (Water Tower)](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) ![Breakfast, lunch, dinner served; American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/6526f50f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Park Hyatt Chicago Downtown Chicago 9.6/10 Exceptional (1000) "beautiful room and hotel great bar!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ravi CA $693 CA $813 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Park-Hyatt-Chicago.h20695.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/30b68b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/4690ab59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/75bfc3f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/bedaec25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton, Chicago Downtown Chicago 9.2/10 Wonderful (1002) "Great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter CA $588 CA $690 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/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) ![Exterior](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/5bfebb1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/bd0f84f5.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 Downtown Chicago 9.2/10 Wonderful (77) "Nice place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $662 CA $777 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-The-St-Regis-Chicago.h91138950.Hotel-Information) ![Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/93a33738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/c0bd1b1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design Townhome, 3 Bedrooms, Kitchen, City View | Living area](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/5df59d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/6cef91d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Art Villa West Town 10/10 Exceptional (2) " " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) tomonobu CA $378 CA $912 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chicago-Hotels-Art-Villa.h115163763.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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Crestwood-Hotels.s50-0-d6960.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Crestwood-Hotels.s50-0-d6960.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 Crestwood. ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St, Chicago, IL CA $177 CA $208 total Nov 16 - Nov 17 includes taxes & fees 8.4/10 Very Good! (5,122 reviews) [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Warwick Allerton - Chicago 701 North Michigan Avenue, Chicago, IL CA $129 CA $192 total Nov 24 - Nov 25 includes taxes & fees 8.4/10 Very Good! (2,911 reviews) [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Pendry Chicago 230 North Michigan Avenue, Chicago, IL CA $252 CA $353 total Nov 23 - Nov 24 includes taxes & fees 9.2/10 Wonderful! (1,116 reviews) [](https://expedia.ca/Chicago-Hotels-Pendry-Chicago.h982552.Hotel-Information) Still don't see what you're looking for? [See all properties in Crestwood.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=6960&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=6960&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=6960&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=6960&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=6960&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=6960&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 Crestwood Explore the sprawling Playfield Park where locals gather for weekend softball tournaments and picnics under shady oak trees. Visit Caesar Park's splash pad in summer, then grab a slice at the family-owned Aurelio's Pizza that's been serving locals since 1959. [See all hotels in Crestwood](https://www.expedia.ca/Hotel-Search?startDate=2025-11-08&endDate=2025-11-09&adults=2®ionId=6960) ![Reflection on Lake at Dusk at Turtlehead Lake Nature Preserve in Orland Park, IL (Suburban Chicago)](https://images.trvl-media.com/place/6960/240c7639-252c-425c-9300-8c5e47f6e396.jpg?impolicy=fcrop&w=900&h=600&p=1&q=high) ## Top Crestwood Hotel Reviews ## Find out more about Crestwood ## Five Star Hotels in Crestwood There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Crestwood so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Crestwood and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Crestwood Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Crestwood The results are in, and Crestwood 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Crestwood! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Crestwood today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Crestwood? > The amount you pay for a 5-star hotel in Crestwood depends on things such as when you plan to go and the length of your escape. A top tip for scoring an awesome deal? Use our pricing filters to check out the available options for your chosen dates. > > > > - Search for the lowest price per night from CA $192 ### What makes a hotel 5 stars in Crestwood? > In Crestwood, a hotel is required to offer a specific level of upscale conveniences to earn a 5-star rating. These can include on-site gyms, saunas and spas, gourmet restaurants, complimentary luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their exceptional standard of service. You'll enjoy things like nightly turn-down services, concierge services and in-room massages. Some may also offer additional touches like welcome gifts. ### Are there any 5-star all-inclusive resorts in Crestwood? > Use our convenient filters to find a high-end retreat in Crestwood where most of what you need is included. Next, refine your results for hotels that have a rating of 5 stars and are described as "All inclusive." The first thing on the itinerary at these stays? 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