Title: 4 Stars Hotels in Southwest Side, Chicago from CA $147 - Find Cheap Southwest Side Hotels With 4 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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495661-chicago-il-mdw-midway-intl.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 4 Stars Hotels in Southwest Side, Chicago from CA $147 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 4 Star Hotels Tonight [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-01&endDate=2025-10-02&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-02&endDate=2025-10-03&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-03&endDate=2025-10-05&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Southwest Side 4 Star Hotels ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/896a6d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/1faa6c2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/9b9a583c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites by Hilton Chicago Downtown River North Downtown Chicago 8.6/10 Excellent (5022) "Really enjoyed our stay!!" CA $271 CA $318 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4.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/1000000/10000/8100/8058/6402f922.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/3fb360e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/e7e820fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago O'Hare Airport O'Hare 8.2/10 Very good (2160) "Very easy check-in and attractive room and restaurant options." CA $249 CA $293 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.Hotel-Information) ![Daily full breakfast (USD 27.76 per person)](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/46cc150a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 Double Beds Premier Tower](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/aa7843d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/57e178a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite Premier Tower](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/87025041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency O'Hare Chicago O'Hare 8.6/10 Excellent (2035) "Nice place to stay! " CA $211 CA $241 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-OHare-Chicago.h5403.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/ca00b143.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/6c4a5051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/e3571b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/d91ad5fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Chicago Hotel Collection - Magnificent Mile Downtown Chicago 7.2/10 Good (1356) "Location was great!" CA $219 CA $257 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/1792d463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 20.00 per person)](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/8967eebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, City View | View from room](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/c06f4b61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Chicago Downtown Downtown Chicago 9.4/10 Exceptional (3897) "Absolutely loved this hotel and location. " CA $283 CA $332 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/023ff9a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/43039f7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/22cb8b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Warwick Allerton - Chicago Downtown Chicago 8.4/10 Very good (2890) "Great location, friendly staff." CA $173 CA $243 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/89e1318d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/5785af38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/42397db2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### InterContinental Chicago Magnificent Mile by IHG Downtown Chicago 9.0/10 Wonderful (2442) "Great stay " CA $374 CA $484 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Lake View](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2561x3y0-ec3252d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/4df3bcb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2695x3y3-e619dd92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Chicago Downtown Chicago 9.4/10 Exceptional (3412) "Great place to stay " CA $348 CA $449 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e85c42c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/511c43ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e50ef89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Hotel Downtown Chicago 8.8/10 Excellent (4696) "Staff friendly and helpful..and accommodations just right..great location! " CA $223 CA $262 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/16c54b79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/dffcca17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/ec9ee4a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Allegro Royal Sonesta Hotel Chicago Loop Downtown Chicago 9.0/10 Wonderful (2100) "We had an amazing stay for a weekend getaway. " CA $222 CA $305 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![City view](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/64dd2430.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/1000000/90000/84800/84736/2e0ab6dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/d8be0ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; Asian cuisine](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/947219c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency McCormick Place Chicago Near South Side 9.2/10 Wonderful (1040) "Excellent stay!" CA $374 CA $472 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-McCormick-Place.h84736.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/6dfbfa42.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/1272603a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/12c82a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L7 Chicago by LOTTE Downtown Chicago 9.6/10 Exceptional (3026) "Amazing hotel and perfectly located" CA $306 CA $360 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b5bf3aa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b812d0f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/bbeef356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago Downtown Chicago 8.4/10 Very good (2232) "Very nice hotel " CA $256 CA $341 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/279c3768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![City view from property](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/2b1c0fd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d2b26aad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Felix River North/Magnificent Mile Downtown Chicago 8.2/10 Very good (2232) "Hotel was nice, staff were friendly, and near attractions and restaurants " CA $169 CA $240 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![1 bedroom, premium bedding, down comforters, pillowtop beds](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/1000000/10000/1400/1346/6d9bcb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/e47956bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/943262bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wade Downtown Chicago 8.4/10 Very good (1335) "Great place to stay" CA $266 CA $312 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/19b0236f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed, Kitchenette](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/01e59f66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/aaae0504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed, Kitchenette](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/a9bc446d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Quarters Hotel, Central Loop, Chicago Downtown Chicago 8.8/10 Excellent (3389) "Very good place to stay" CA $182 CA $214 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h565746.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/aaad0ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/01c93cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palmer House a Hilton Hotel Downtown Chicago 8.4/10 Very good (2001) "Great property with great staff and amenities. " CA $264 CA $345 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/9600/9529/8f0b88a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9529/1ed17318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/9600/9529/5db910fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/9600/9529/5ac21fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Lisle Naperville Naperville 7.8/10 Good (1175) "Great stay " CA $133 CA $147 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Lisle-Naperville.h9529.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6600/6545/8dd24dc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/6600/6545/585e65d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/6600/6545/0b02dca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/6600/6545/b44ba019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove Wood Dale 8.2/10 Very good (1041) "Pretty decent place." CA $136 CA $151 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Wood-Dale-Elk-Grove.h6545.Hotel-Information) ![Executive lounge](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/2e9bef56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/84fcc5bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Steam room, body treatments, facials, 2 treatment rooms, massages](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/b376d4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairmont Chicago at Millennium Park Downtown Chicago 8.6/10 Excellent (1967) "Perfect location!" CA $354 CA $456 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Chicago-Hotels-Fairmont-Chicago-At-Millennium-Park.h15937.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%2F4Star-Southwest-Side-Hotels.s40-0-d553248635976475403.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Southwest-Side-Hotels.s40-0-d553248635976475403.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Southwest Side. ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Trump International Hotel & Tower Chicago 401 N Wabash Ave, Chicago, IL CA $642 CA $754 total Oct 19 - Oct 20 includes taxes & fees 9.4/10 Exceptional! (1,745 reviews) [](https://expedia.ca/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information) ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Langham, Chicago 330 North Wabash Avenue, Chicago, IL CA $793 CA $931 total Oct 26 - Oct 27 includes taxes & fees 9.6/10 Exceptional! (1,012 reviews) [](https://expedia.ca/Chicago-Hotels-The-Langham.h6309326.Hotel-Information) ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Peninsula Chicago 108 East Superior Street, Chicago, IL CA $940 CA $1,103 total Oct 5 - Oct 6 includes taxes & fees 9.6/10 Exceptional! (1,013 reviews) [](https://expedia.ca/Chicago-Hotels-The-Peninsula-Chicago.h581213.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=02%2F10%2F2025&endDate=03%2F10%2F2025®ionId=553248635976475403&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=02%2F10%2F2025&endDate=03%2F10%2F2025®ionId=553248635976475403&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=02%2F10%2F2025&endDate=03%2F10%2F2025®ionId=553248635976475403&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=02%2F10%2F2025&endDate=03%2F10%2F2025®ionId=553248635976475403&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=02%2F10%2F2025&endDate=03%2F10%2F2025®ionId=553248635976475403&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=02%2F10%2F2025&endDate=03%2F10%2F2025®ionId=553248635976475403&star=40&star=40&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=2025-10-15&endDate=2025-10-16&adults=2®ionId=553248635976475403) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495661-chicago-il-mdw-midway-intl.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) Photo by by Midway Intl Airport ## Top Southwest Side Hotel Reviews ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "Rooms were clean and staff were always happy to help " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "We had a fantastic stay at the Embassy Suites by Hilton Chicago Downtown River North. Our suite was impressively clean and offered plenty of space to spread out, which made it especially comfortable for a multi-day visit. Everything felt well maintained and tidy, which gave us peace of mind right from the start. The location was another highlight. Being in River North meant we were close to great restaurants, shopping, and attractions, and having the subway nearby made getting around the city easy and convenient. It was the perfect base for exploring Chicago. Breakfast was outstanding and far above the standard hotel fare. There were lots of options to choose from, including fresh fruit, pastries, hot items, and the standout feature—a station for custom-made omelets. It was a great way to start each day, and the variety meant there was something for everyone. Overall, Embassy Suites River North checked all the boxes: clean, spacious, well-located, and with excellent breakfast to top it off. We would happily stay here again on our next trip to Chicago." [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![The Chicago Hotel Collection - Magnificent Mile](//images.trvl-media.com/lodging/1000000/30000/21700/21619/ca00b143_y.jpg) ### The Chicago Hotel Collection - Magnificent Mile 10/10 Excellent "Room was a little run down, but everything was amazing!" [](https://expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information) ![Hyatt Regency Chicago](//images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "Everything was on point" [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![DoubleTree by Hilton Chicago - Magnificent Mile](//images.trvl-media.com/lodging/1000000/30000/21200/21152/b1113923_y.jpg) ### DoubleTree by Hilton Chicago - Magnificent Mile 10/10 Excellent "Great" [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "Clean room, free wine bottle and water bottles were provided daily. Great location! Everything within 15-20 minute walk. Omar, the bartender was excellent and super friendly! Had great suggestions on where to go to eat and entertainment and made great drinks! I would stay there again and great price too! " [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![Hotel Felix River North/Magnificent Mile](//images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg) ### Hotel Felix River North/Magnificent Mile 10/10 Excellent "Great location to walk to everything " [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![Sable at Navy Pier Chicago, Curio Collection by Hilton](//images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg) ### Sable at Navy Pier Chicago, Curio Collection by Hilton 10/10 Excellent "Great hotel " [](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "Excellent location. The hotel was clean and the staff were friendly. The room was very small, but we knew that when we booked. " [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ## Find out more about Southwest Side If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Southwest Side are calling your name. Known for providing first-rate service in amazing locations, each of the Southwest Side 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Southwest Side. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Southwest Side, Chicago, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Southwest Side hotels with 4 Stars provide everything you need to unwind in style. ## 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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[Hotels near Midway Intl.](https://www.expedia.ca/Midway-Intl-Airport-Hotels.0-aMDW-0.Travel-Guide-Filter-Hotels) - [B&B in Midway Station](https://www.expedia.ca/Midway-Station-Bed-And-Breakfast.d6211025-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Midway Station](https://www.expedia.ca/Midway-Station-Hotels.d6211025.Travel-Guide-Hotels) - [Motels in Midway Station](https://www.expedia.ca/Midway-Station-Motels.d6211025-aaMotels.Travel-Guide-Accommodation) - [Beach Hotel Hotels in New City](https://www.expedia.ca/New-City-Chicago-Hotels-Beach-Hotel.0-n6132388-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in New City](https://www.expedia.ca/New-City-Chicago-Hotels-Boutique-Hotel.0-n6132388-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in New City](https://www.expedia.ca/New-City-Chicago-Hotels-Hotel-With-Pool.0-n6132388-0-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in New City](https://www.expedia.ca/New-City-Chicago-Hotels-LGBT-Friendly-Hotel.0-n6132388-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - 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[West Lawn Hotels](https://www.expedia.ca/West-Lawn-Chicago-Hotels.0-n6132413-0.Travel-Guide-Filter-Hotels) - [Hotels near Zhou B Art Center](https://www.expedia.ca/Zhou-B-Art-Center-Hotels.0-l553248621533116323-0.Travel-Guide-Filter-Hotels) - [Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights from Midway Intl.](https://www.expedia.ca/lp/airports/mdw/flights-from-midway-intl-airport) - [Porter Airlines Toronto (YTZ) to Chicago (MDW) flights](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-billy-bishop-toronto-city-to-midway-intl/pd/ytz/mdw) - [Flights from Toronto (YTZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago) - [Flights from Toronto (YYZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Visit Back of the Yards](https://www.expedia.ca/Chicago-Back-Of-The-Yards.dx553248635976382392) - [Visit Brighton Park](https://www.expedia.ca/Chicago-Brighton-Park.dx6132396) - [Visit Canaryville](https://www.expedia.ca/Chicago-Canaryville.dx6132307) - [Visit Chicago Lawn](https://www.expedia.ca/Chicago-Chicago-Lawn.dx6132188) - [Visit Englewood](https://www.expedia.ca/Chicago-Englewood.dx101911) - [Visit Gage Park](https://www.expedia.ca/Chicago-Gage-Park.dx6132375) - [Car rentals near McKinley Park](https://www.expedia.ca/Car-Rentals-In-McKinley-Park.d6132389.Car-Rental-Guide) - [Rental cars Midway Intl. airport](https://www.expedia.ca/Car-Rentals-In-Midway-Intl.d5719117.Car-Rental-Guide) - [Book 4 Star Hotels in Southwest Side on Expedia.com](https://www.expedia.com/4Star-Southwest-Side-Hotels.s40-0-d553248635976475403.Travel-Guide-Filter-Hotels)