Title: The 10 Best 4 Star Hotels in Southwest Side - 2025 Updated Prices | Expedia.co.uk [Southwest Side Travel Guide](https://expedia.co.uk/Southwest-Side.dx553248635976475403)[Hotels in Southwest Side](https://expedia.co.uk/Southwest-Side-Hotels.d553248635976475403.Travel-Guide-Hotels)[Holiday Rentals in Southwest Side](https://expedia.co.uk/Southwest-Side-Holiday-Rentals.d553248635976475403.Travel-Guide-HolidayRentals)[Flights to Southwest Side](https://expedia.co.uk/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights)[Southwest Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Southwest-Side.d553248635976475403.Car-Hire-Guide)[Southwest Side Holidays](https://expedia.co.uk/Southwest-Side.d553248635976475403.Holidays-City-Breaks) ![](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) # Compare and book 4 Star hotels in Southwest Side, Chicago ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.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 Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![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 [20 Sept - 21 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-09-20&endDate=2025-09-21&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [21 Sept - 22 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-09-21&endDate=2025-09-22&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [26 Sept - 28 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-09-26&endDate=2025-09-28&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [3 Oct - 5 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-10-03&endDate=2025-10-05&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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/9b9a583c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast ](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/0a522c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, pillow-top 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) ### Embassy Suites by Hilton Chicago Downtown River North Downtown Chicago 8.6/10 Excellent (4971) "Really enjoyed our stay!!" £161 includes taxes & fees 22 Sept - 23 Sept [](https://www.expedia.co.uk/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 duvets, pillow-top 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) ![2 restaurants, breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/417e48d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago O'Hare Airport O'Hare 8.2/10 Very good (2141) "Very easy check-in and attractive room and restaurant options." £187 includes taxes & fees 18 Oct - 19 Oct [](https://www.expedia.co.uk/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 | Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/aa7843d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite Premier Tower | Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/87025041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/d075b709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency O'Hare Chicago O'Hare 8.6/10 Excellent (1995) "Beautiful hotel. " £144 includes taxes & fees 27 Sept - 28 Sept [](https://www.expedia.co.uk/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 lounge](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/d91ad5fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/67428c96.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) ### The Chicago Hotel Collection - Magnificent Mile Downtown Chicago 7.2/10 Good (1324) "Great location for restaurants, shopping and seeing the city" £127 includes taxes & fees 22 Sept - 23 Sept [](https://www.expedia.co.uk/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) ![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) ![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) ### citizenM Chicago Downtown Downtown Chicago 9.4/10 Exceptional (3822) "Great place to stay for a quick trip!" £136 includes taxes & fees 22 Sept - 23 Sept [](https://www.expedia.co.uk/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) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/ccacdd84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room | 1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/22cb8b3e.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) ### Warwick Allerton - Chicago Downtown Chicago 8.4/10 Very good (2930) "Great spot with friendly staff and an incredible location" £124 includes taxes & fees 22 Sept - 23 Sept [](https://www.expedia.co.uk/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/1000000/30000/20300/20205/6aceeeea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, Egyptian cotton sheets, premium bedding, down duvets](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/42397db2.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) ### InterContinental Chicago Magnificent Mile by IHG Downtown Chicago 9.0/10 Wonderful (2400) "Great stay " £267 includes taxes & fees 22 Sept - 23 Sept [](https://www.expedia.co.uk/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 | 1 bedroom, premium bedding, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2561x3y0-ec3252d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/fb110cc2.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) ### Hyatt Regency Chicago Downtown Chicago 9.2/10 Wonderful (3370) "Beautiful hotel and very convenient to shopping " £270 includes taxes & fees 3 Oct - 4 Oct [](https://www.expedia.co.uk/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) ![Standard Room, 2 Single Beds | Premium bedding, desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/6d4883c6.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) ![Meeting facility](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e85c42c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Hotel Downtown Chicago 8.8/10 Excellent (4687) "Friendly staff and great location!" £140 includes taxes & fees 20 Oct - 21 Oct [](https://www.expedia.co.uk/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) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/ec9ee4a6.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) ![Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/16c54b79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Allegro Royal Sonesta Hotel Chicago Loop Downtown Chicago 9.0/10 Wonderful (2038) "Excellent place to stay" £193 includes taxes & fees 2 Oct - 3 Oct [](https://www.expedia.co.uk/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 duvets, pillow-top 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) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/df55aaa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency McCormick Place Chicago Near South Side 9.0/10 Wonderful (1027) "Excellent stay!" £243 includes taxes & fees 25 Sept - 26 Sept [](https://www.expedia.co.uk/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/1000000/10000/4200/4200/1272603a.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) ![Suite, 1 Bedroom, River View | View from room](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/c80457b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L7 Chicago by LOTTE Downtown Chicago 9.6/10 Exceptional (2981) "Excellent location, staff was very friendly" £227 includes taxes & fees 26 Sept - 27 Sept [](https://www.expedia.co.uk/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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/f2c5642d.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) ![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) ### Hilton Chicago Downtown Chicago 8.4/10 Very good (2218) "Amazing stay and great location…" £204 includes taxes & fees 25 Sept - 26 Sept [](https://www.expedia.co.uk/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) ![Interior entrance](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/9097f753.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 (2194) "Loved our stay" £114 includes taxes & fees 22 Sept - 23 Sept [](https://www.expedia.co.uk/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![1 bedroom, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/943262bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](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) ### The Wade Downtown Chicago 8.4/10 Very good (1299) "Overall was a great stay" £166 includes taxes & fees 2 Oct - 3 Oct [](https://www.expedia.co.uk/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 | 1 bedroom, premium bedding, in-room safe, desk](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/1000000/570000/565800/565746/9378ca8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed, Kitchenette | 1 bedroom, premium bedding, in-room safe, desk](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 (3362) "Very good place to stay" £127 includes taxes & fees 5 Oct - 6 Oct [](https://www.expedia.co.uk/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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.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) ### Palmer House a Hilton Hotel Downtown Chicago 8.4/10 Very good (1977) "Wonderful historic property, we loved our stay in this beautiful hotel" £233 includes taxes & fees 2 Oct - 3 Oct [](https://www.expedia.co.uk/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) ![Pillow-top beds, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/10000/9600/9529/06e4d0df.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9529/1ed17318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Lisle Naperville Naperville 7.8/10 Good (1150) "Great stay " £72 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/6600/6545/48bc466d.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 (1013) "It was a very nice hotel ." £80 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/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 duvets, pillow-top beds, minibar](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/2e9bef56.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/1000000/20000/16000/15937/037db98f.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) ### Fairmont Chicago at Millennium Park Downtown Chicago 8.6/10 Excellent (1934) "Great stay " £282 includes taxes & fees 2 Oct - 3 Oct [](https://www.expedia.co.uk/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.co.uk/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.co.uk/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 £402 5 Oct - 6 Oct includes taxes & fees 9.4/10 Exceptional! (1,716 reviews) [](https://expedia.co.uk/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 £529 5 Oct - 6 Oct includes taxes & fees 9.6/10 Exceptional! (1,005 reviews) [](https://expedia.co.uk/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 £545 28 Sept - 29 Sept includes taxes & fees 9.6/10 Exceptional! (1,007 reviews) [](https://expedia.co.uk/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.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F09%2F2025&endDate=23%2F09%2F2025®ionId=553248635976475403&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F09%2F2025&endDate=23%2F09%2F2025®ionId=553248635976475403&star=40&star=40&amenities=POOL)[Spa](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F09%2F2025&endDate=23%2F09%2F2025®ionId=553248635976475403&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F09%2F2025&endDate=23%2F09%2F2025®ionId=553248635976475403&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F09%2F2025&endDate=23%2F09%2F2025®ionId=553248635976475403&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F09%2F2025&endDate=23%2F09%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.co.uk/Hotel-Search?startDate=2025-10-05&endDate=2025-10-06&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 ![Palmer House a Hilton Hotel](//images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "This is a beautiful hotel and so conveniently located - easy to walk to museums and the Mag Mile" [](https://expedia.co.uk/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.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 "Liked convenient location. Nearby transportation facility. Very nice place to stay!" [](https://expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Hilton Chicago](//images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "Easy parking and walkable to all the fun stuff in under 10 mins. And bonus my room was really really comfortable!" [](https://expedia.co.uk/Chicago-Hotels-Hilton-Chicago.h12570.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 "Great" [](https://expedia.co.uk/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "I loved the character and asthetic of the interior. It was classy, some areas have seen some heavy traffic but it builds the character of the place. I had a shared room with 3 others mostly just kept to ourselves other than a hello or good morning. Staff were very helpful if i had any questions. My only complaint is the price of the drinks" [](https://expedia.co.uk/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "Great spot with friendly staff and an incredible location" [](https://expedia.co.uk/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.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 "Enjoyed a wonderful stay at Hotel Felix while we were in town for a Lady GaGa concert. Room was clean and comfortable. Staff was very friendly and helpful." [](https://expedia.co.uk/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![citizenM Chicago Downtown](//images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd_y.jpg) ### citizenM Chicago Downtown 10/10 Excellent "Please try to restock luggage tag bands" [](https://expedia.co.uk/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information) ![River Hotel](//images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg) ### River Hotel 10/10 Excellent "Very clean and friendly people working there! They were very helpful " [](https://expedia.co.uk/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ## Find out more about Southwest Side ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - More ways to book - [1 Star Hotels in Chicago](https://www.expedia.co.uk/1Star-Chicago-Hotels.s10-0-d178248.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Chicago](https://www.expedia.co.uk/2Star-Chicago-Hotels.s20-0-d178248.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Northwest Side](https://www.expedia.co.uk/2Star-Northwest-Side-Hotels.s20-0-d553248635976475367.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Chicago](https://www.expedia.co.uk/3Star-Chicago-Hotels.s30-0-d178248.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Elmhurst](https://www.expedia.co.uk/3Star-Elmhurst-Hotels.s30-0-d7836.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Lincoln Park](https://www.expedia.co.uk/3Star-Lincoln-Park-Chicago-Hotels.s30-n6059328-0.Travel-Guide-Filter-Hotels) - 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[Flights from St. Cloud (STC) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/stc/mdw/st-cloud-to-chicago) - [Flights from Fayetteville (XNA) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/xna/mdw/fayetteville-to-chicago) - [Flights from Windsor (YQG) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/yqg/mdw/windsor-to-chicago) - [Visit Brighton Park](https://www.expedia.co.uk/Chicago-Brighton-Park.dx6132396) - [Visit Chicago Lawn](https://www.expedia.co.uk/Chicago-Chicago-Lawn.dx6132188) - [Visit Gage Park](https://www.expedia.co.uk/Chicago-Gage-Park.dx6132375) - [Visit Grand Boulevard](https://www.expedia.co.uk/Chicago-Grand-Boulevard.dx6132310) - [Visit Little Village](https://www.expedia.co.uk/Chicago-Little-Village.dx6132436) - [Visit West Elsdon](https://www.expedia.co.uk/Chicago-West-Elsdon.dx6132410) - [Chicago Holidays](https://www.expedia.co.uk/Chicago.d178248.Holidays-City-Breaks) - [S.s. Peter and Paul Church](https://www.expedia.co.uk/SS-Peter-And-Paul-Church-McKinley-Park.d6247219.Attraction) - [Rental cars Midway Intl. airport](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Midway-Intl.d5719117.Car-Hire-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)