Title: 5 Stars Hotels in Northwest Side, Chicago from CA $151 - Find Cheap Northwest Side Hotels With 5 Stars | Expedia.ca [Northwest Side Travel Guide](https://expedia.ca/Northwest-Side.dx553248635976475367)[Hotels in Northwest Side](https://expedia.ca/Northwest-Side-Hotels.d553248635976475367.Travel-Guide-Hotels)[Vacation Rentals in Northwest Side](https://expedia.ca/Northwest-Side-Vacation-Rentals.d553248635976475367.Travel-Guide-VacationRentals)[Flights to Northwest Side](https://expedia.ca/Cheap-Flights-To-Northwest-Side.d553248635976475367.Travel-Guide-Flights)[Northwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Northwest-Side.d553248635976475367.Car-Rental-Guide)[Northwest Side Vacation Packages](https://expedia.ca/Northwest-Side.d553248635976475367.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/829/2253d64b-0974-4770-85a9-32842b88f38f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Northwest Side, Chicago from CA $151 - ![](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 Northwest Side 5 Star Hotels Tonight [Nov 30 - Dec 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976475367&startDate=2025-11-30&endDate=2025-12-01&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 1 - Dec 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976475367&startDate=2025-12-01&endDate=2025-12-02&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976475367&startDate=2025-12-05&endDate=2025-12-07&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976475367&startDate=2025-12-12&endDate=2025-12-14&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Northwest Side 5 Star Hotels ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/7da48e89.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) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/ee956af2.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 (1005) "Amazing hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $587 CA $689 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Chicago-Hotels-Four-Seasons-Hotel-Chicago.h25748.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/0c7c3240.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 (1007) "Spa ,pool are awesome " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jared CA $638 CA $749 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Chicago-Hotels-The-Langham.h6309326.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) ![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) ![Couples treatment rooms, body treatments, hydrotherapy, aromatherapy](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/6ca152e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Peninsula Chicago Downtown Chicago 9.8/10 Exceptional (1017) "Great rooms, location and top flight service" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew CA $707 CA $830 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Chicago-Hotels-The-Peninsula-Chicago.h581213.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) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gym](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4f5517f6.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 (1788) "Excellent place to stay in Chicago. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom CA $514 CA $603 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.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) ![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) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/cc9f9fd8.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) ### Waldorf Astoria Chicago Downtown Chicago 9.4/10 Exceptional (1007) "Simply love this hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) laura CA $553 CA $650 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Chicago-Hotels-Waldorf-Astoria-Chicago.h2717582.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/ca3d604d.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 (1002) "Stay was amazing!!! The staff was so friendly, kind, and thoughtful! The rooms were soooo beyond perfect and lovely! And the food at the restaurant was amazing.. especially breakfast! You won’t regret staying here!!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Larissa CA $629 CA $738 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Chicago-Hotels-Park-Hyatt-Chicago.h20695.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) ![Terrace/patio](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/37b7786f.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 (752) "Great location, amenities and staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas CA $350 CA $411 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Chicago-Hotels-Nobu-Hotel-Chicago.h36475533.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/4690ab59.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/2fe2113a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton, Chicago Downtown Chicago 9.2/10 Wonderful (1005) "Great breakfast a la carte menu, perfect bar setting, room was spotless, and service in accordance to the Ritz Brand." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alejandro Randolph CA $540 CA $634 total includes taxes & fees Dec 30 - Dec 31 [](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) ![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) ![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) ### The St. Regis Chicago Downtown Chicago 9.2/10 Wonderful (83) "Nice place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $623 CA $732 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Chicago-Hotels-The-St-Regis-Chicago.h91138950.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/00656023.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 | Terrace/patio](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/93a33738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/5d5af9bf.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 [](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-Northwest-Side-Hotels.s50-0-d553248635976475367.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Northwest-Side-Hotels.s50-0-d553248635976475367.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 Northwest Side. ![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 $129 CA $151 total Dec 7 - Dec 8 includes taxes & fees 8.4/10 Very Good! (5,334 reviews) [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Palmer House a Hilton Hotel 17 E Monroe St Chicago IL CA $149 CA $210 total Dec 28 - Dec 29 includes taxes & fees 8.4/10 Very Good! (2,090 reviews) [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hilton Chicago O'Hare Airport O'Hare International Airport Chicago IL CA $274 CA $322 total Dec 20 - Dec 21 includes taxes & fees 8.2/10 Very Good! (2,183 reviews) [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.Hotel-Information) Still don't see what you're looking for? [See all properties in Northwest Side.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F12%2F2025&endDate=02%2F12%2F2025®ionId=553248635976475367&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=01%2F12%2F2025&endDate=02%2F12%2F2025®ionId=553248635976475367&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F12%2F2025&endDate=02%2F12%2F2025®ionId=553248635976475367&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F12%2F2025&endDate=02%2F12%2F2025®ionId=553248635976475367&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F12%2F2025&endDate=02%2F12%2F2025®ionId=553248635976475367&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F12%2F2025&endDate=02%2F12%2F2025®ionId=553248635976475367&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 Northwest Side Check out the local area in Northwest Side—home to attractions like Walt Disney House and Milwaukee Avenue. [See all hotels in Northwest Side](https://www.expedia.ca/Hotel-Search?startDate=2025-12-14&endDate=2025-12-15&adults=2®ionId=553248635976475367) ![](https://images.trvl-media.com/place/829/2253d64b-0974-4770-85a9-32842b88f38f.jpg?impolicy=fcrop&w=400&h=400&p=1&q=high) ## Top Northwest Side Hotel Reviews ## Find out more about Northwest Side Luxury is the name of the game at the best 5 Stars hotels in Northwest Side. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Northwest Side 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them. Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Northwest Side hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Northwest Side without giving up even an inch of quality. 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