Title: 5 Stars Hotels in Southwest Side, Chicago from CA $175 - Find Cheap Southwest Side Hotels With 5 Stars | Expedia.ca [Southwest Side Travel Guide](https://expedia.ca/Southwest-Side.dx553248635976475403)[Hotels in Southwest Side](https://expedia.ca/Southwest-Side-Hotels.d553248635976475403.Travel-Guide-Hotels)[Vacation Rentals in Southwest Side](https://expedia.ca/Southwest-Side-Vacation-Rentals.d553248635976475403.Travel-Guide-VacationRentals)[Flights to Southwest Side](https://expedia.ca/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights)[Southwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Southwest-Side.d553248635976475403.Car-Rental-Guide)[Southwest Side Vacation Packages](https://expedia.ca/Southwest-Side.d553248635976475403.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 availability on Southwest Side 5 Star Hotels Tonight [Jan 16 - Jan 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-01-16&endDate=2026-01-17&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 17 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-01-17&endDate=2026-01-18&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-01-16&endDate=2026-01-18&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-01-23&endDate=2026-01-25&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Southwest Side 5-star hotels ![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) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/7da48e89.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) ### Four Seasons Hotel Chicago [](https://www.expedia.ca/Chicago-Hotels-Four-Seasons-Hotel-Chicago.h25748.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (999 reviews) "Excellent customer service and we loved the room and accommodations." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean [](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) ![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) ![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) ### The Langham, Chicago [](https://www.expedia.ca/Chicago-Hotels-The-Langham.h6309326.Hotel-Information) Downtown Chicago 9.8/10 Exceptional (1,000 reviews) "Love the langham!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Clayton [](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) ![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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/acbf2aab.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) ### The Peninsula Chicago [](https://www.expedia.ca/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information) Downtown Chicago 9.8/10 Exceptional (1,000 reviews) "Loved the location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark [](https://www.expedia.ca/Chicago-Hotels-The-Peninsula-Chicago.h581213.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) ![Body treatments, body wraps, body scrubs, facials](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/838eb9bb.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) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/c665b589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trump International Hotel & Tower Chicago [](https://www.expedia.ca/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1,817 reviews) "The location was more than perfect!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CHRISTOPHER [](https://www.expedia.ca/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.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) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/dfd1e89b.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/d1b25ed0.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 [](https://www.expedia.ca/Chicago-Hotels-Waldorf-Astoria-Chicago.h2717582.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1,000 reviews) "Super comfortable bed, and the deep bathtub alone is worth the stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacqueline [](https://www.expedia.ca/Chicago-Hotels-Waldorf-Astoria-Chicago.h2717582.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 (Gold Coast) | View from room](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/aa0a7cb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Park Hyatt Chicago [](https://www.expedia.ca/Chicago-Hotels-Park-Hyatt-Chicago.h20695.Hotel-Information) Downtown Chicago 9.6/10 Exceptional (1,000 reviews) "Room was excellent. Everything was clean and the amenities were fantastic. Staff was very warm and helpful. Will go back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](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) ![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) ### Nobu Hotel Chicago [](https://www.expedia.ca/Chicago-Hotels-Nobu-Hotel-Chicago.h36475533.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (777 reviews) "Room was great and spacious. Service was great. The pool and sauna were nice also. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria [](https://www.expedia.ca/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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/4690ab59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton, Chicago [](https://www.expedia.ca/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 [](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) ![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) ![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) ### The St. Regis Chicago [](https://www.expedia.ca/Chicago-Hotels-The-St-Regis-Chicago.h91138950.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (90 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 [](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) ![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) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/57a475a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Art Villa [](https://www.expedia.ca/Chicago-Hotels-Art-Villa.h115163763.Hotel-Information) West Town 10/10 Exceptional (2 reviews) [](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-Southwest-Side-Hotels.s50-0-d553248635976475403.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Southwest-Side-Hotels.s50-0-d553248635976475403.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 Southwest 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 $149 CA $175 total Jan 19 - Jan 20 includes taxes & fees 8.4/10 Very Good! (5,538 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 $198 CA $267 total Jan 22 - Jan 23 includes taxes & fees 8.4/10 Very Good! (2,239 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 $272 CA $319 total Feb 7 - Feb 8 includes taxes & fees 8.2/10 Very Good! (2,182 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 Southwest Side.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F01%2F2026&endDate=18%2F01%2F2026®ionId=553248635976475403&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=17%2F01%2F2026&endDate=18%2F01%2F2026®ionId=553248635976475403&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F01%2F2026&endDate=18%2F01%2F2026®ionId=553248635976475403&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F01%2F2026&endDate=18%2F01%2F2026®ionId=553248635976475403&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F01%2F2026&endDate=18%2F01%2F2026®ionId=553248635976475403&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F01%2F2026&endDate=18%2F01%2F2026®ionId=553248635976475403&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 Southwest Side Explore attractions like Balzekas Museum of Lithuanian Culture and Union Stock Yard Gate as you discover things to see and do in Southwest Side. [See all hotels in Southwest Side](https://www.expedia.ca/Hotel-Search?startDate=2026-01-30&endDate=2026-01-31&adults=2®ionId=553248635976475403) ![Chicago, IL showing interior views, heritage elements and an airport](https://images.trvl-media.com/place/5719117/ef1b962b-07e6-469b-abf5-73ab99ceb6ee.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) Photo by by Midway Intl Airport ## Top Southwest Side Hotel Reviews ## Find out more about Southwest Side Luxury is the name of the game at the best 5 Stars hotels in Southwest 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 Southwest 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 Southwest 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 Southwest Side without giving up even an inch of quality. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in Southwest Side. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [1 Star Hotels in Chicago ](https://www.expedia.ca/1Star-Chicago-Hotels.s10-0-d178248.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Far Southwest Side ](https://www.expedia.ca/1Star-Far-Southwest-Side-Hotels.s10-0-d553248635976475353.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Gano ](https://www.expedia.ca/1Star-Gano-Chicago-Hotels.s10-n6132380-0.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Grace Abbott Homes ](https://www.expedia.ca/1Star-Grace-Abbott-Homes-Chicago-Hotels.s10-n6132393-0.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Sheffield and DePaul ](https://www.expedia.ca/1Star-Sheffield-And-DePaul-Chicago-Hotels.s10-n553248635976474890-0.Travel-Guide-Filter-Hotels) - [1 Star Hotels in South Englewood ](https://www.expedia.ca/1Star-South-Englewood-Chicago-Hotels.s10-n6132433-0.Travel-Guide-Filter-Hotels) - 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