Title: Book the Best SHOPPING Hotels in South Side in 2026 | Expedia.ca [South Side Travel Guide](https://expedia.ca/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.ca/South-Side.d553248635074842823.Destination-Travel-Guides) ![Chicago South Side](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.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 South Side Shopping Hotels Tonight [Jan 26 - Jan 27](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-26&endDate=2026-01-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 27 - Jan 28](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-27&endDate=2026-01-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side hotels with shopping nearby ![Smart TV, video games](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1350h899x0y1-166f73c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1350h899x0y1-43718ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/2b5be5e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1350h899x0y1-09740a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6 [](https://www.expedia.ca/Chicago-Hotels-Sunflower-Apt-10-Min-From-Downtown-Chicago-Sleeps-Up-To-6.h91086437.Hotel-Information) Brighton Park 8.6/10 Excellent (20 reviews) "Clean and nice. My son loved the arcade game. Would stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nichole S. CA $75 CA $272 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Chicago-Hotels-Sunflower-Apt-10-Min-From-Downtown-Chicago-Sleeps-Up-To-6.h91086437.Hotel-Information) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/494ee0d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/78f90795.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/f6f934a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/c3e19322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Contemporary 2BR Apartment in Vibrant Hyde Park [](https://www.expedia.ca/Chicago-Hotels-Contemporary-2BR-Apartment-In-Vibrant-Hyde-Park.h116792547.Hotel-Information) Hyde Park 10/10 Exceptional (1 review) "We stayed in this comfortable, quiet apartment for four weeks when my husband was undergoing radiation treatments for cancer at the University of Chicago Medical Center. It was just what we needed. The location—a block from Lake Michigan with its endless miles of parks and green spaces—was spectacular, and we spent long hours walking our dogs and biking along the lake on the beautifully landscaped walking and biking trails. The apartment itself is well appointed, clean, and blessedly quiet... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heidi H. CA $79 CA $245 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Chicago-Hotels-Contemporary-2BR-Apartment-In-Vibrant-Hyde-Park.h116792547.Hotel-Information) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792638/262ae72d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792638/c2f1c810.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792638/5a5871f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792638/29086b5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright & Spacious 2BR– Prime Hyde Park Location [](https://www.expedia.ca/Chicago-Hotels-Bright-Spacious-2BR-Prime-Hyde-Park-Location.h116792638.Hotel-Information) Hyde Park 7.0/10 Good (2 reviews) "Great stay! The owners were easy to communicate with and were accompanying! The property was clean and close to stores, restaurants, and shops! Would stay again in the future! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeremy M. CA $79 CA $252 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Chicago-Hotels-Bright-Spacious-2BR-Prime-Hyde-Park-Location.h116792638.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/1c7b677d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/8318473d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/832f7b8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palmer House a Hilton Hotel [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) Downtown Chicago 8.6/10 Excellent (2,272 reviews) "Excellent stay, we loved it " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melani CA $184 CA $251 total includes taxes & fees Feb 21 - Feb 22 [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e43f096f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/086ff612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, City View | City view](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/3e0e58e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Congress Plaza Hotel [](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) Downtown Chicago 8.0/10 Very good (9,828 reviews) "Staff was nice, clean room, nice location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zyanya CA $121 CA $142 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/4bc08adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/5e323fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/72004781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/64fc97f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Godfrey Hotel Chicago [](https://www.expedia.ca/Chicago-Hotels-The-Godfrey-Hotel-Chicago.h7063210.Hotel-Information) Downtown Chicago 8.6/10 Excellent (2,013 reviews) "Clean rooms, great staff, and great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Romel CA $98 CA $147 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Chicago-Hotels-The-Godfrey-Hotel-Chicago.h7063210.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/461957e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/6234383e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/b90174ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/3a5d3e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Chicago Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (1,070 reviews) "Amazing location, excellent service and great pool and hot tub. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tim CA $151 CA $217 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121360000/121358700/121358639/66c2b5bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/122000000/121360000/121358700/121358639/cafdea3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/122000000/121360000/121358700/121358639/f0c5f788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/122000000/121360000/121358700/121358639/b026571f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Prime Location! Indoor Pool, Near Millenium Park, Shedd Aquarium, Willis Tower [](https://www.expedia.ca/Chicago-Hotels-Prime-Location-Indoor-Pool.h121358639.Hotel-Information) Downtown Chicago 10/10 Exceptional (1 review) "It was good " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ganiah J. CA $132 CA $188 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Chicago-Hotels-Prime-Location-Indoor-Pool.h121358639.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/118000000/117300000/117295000/117294952/186f3445.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/118000000/117300000/117295000/117294952/832ddfd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117300000/117295000/117294952/49c541b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117300000/117295000/117294952/ff0f80e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Room with Rooftop Lounge & City Views in River North [](https://www.expedia.ca/Chicago-Hotels-Cozy-Room-With-Rooftop-Lounge-City-Views-In-River-North.h117294952.Hotel-Information) Downtown Chicago 10/10 Exceptional (1 review) "The hotel was very nice and the location was excellent. Was able to walk to many locations. Noise wasn't bad for a city experience. Hotel restaurant was very good." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cathy L. CA $141 CA $232 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Chicago-Hotels-Cozy-Room-With-Rooftop-Lounge-City-Views-In-River-North.h117294952.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/118000000/117300000/117295000/117294947/5acb8650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117300000/117295000/117294947/e77ae66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117300000/117295000/117294947/5950d1c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117300000/117295000/117294947/fed8d0a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Unit with Rooftop Lounge & Spectacular City Views [](https://www.expedia.ca/Chicago-Hotels-Luxury-Unit-With-Rooftop-Lounge-Spectacular-City-Views.h117294947.Hotel-Information) Downtown Chicago 10/10 Exceptional (1 review) "Great Chicago location. Close to everything. Check in was a breeze. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debbie F. CA $118 CA $204 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Chicago-Hotels-Luxury-Unit-With-Rooftop-Lounge-Spectacular-City-Views.h117294947.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-09&endDate=2026-02-10®ionId=553248635074842823&adults=2&location_highlights_explore=shopping&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/65c30d17_y.jpg) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG 10/10 Excellent "Room was spotless, staff was great. Would definitely stay here again " [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Clean room. Friendly & helpful staff. Convenient location. " [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Hyatt Place Chicago-South/University Medical Center](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg) ### Hyatt Place Chicago-South/University Medical Center 10/10 Excellent "All great!" [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/w3836h2161x5y0-7f85e9e1_y.jpg) ### Holiday Inn Chicago – Midway Airport S by IHG 10/10 Excellent "I was greeted with a smile we checking our room and we were late. They were very accommodating. They have a bar which we went over to eat from. I don’t know the bartender’s real name we were cold to call her TT. She was the very best ever very kind very sociable and friendly. I will be returning to this property the next time I’m in Chicago. I really had a great experience at this hotel with the staff is also includes the manager the hotel clerk, as well as the security guard. I will give my experience at this hotel five stars." [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information) ![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg) ### Chinatown Hotel Chicago 10/10 Excellent "Get what you pay for! " [](https://expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) ![Chicago Marriott Midway](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg) ### Chicago Marriott Midway 10/10 Excellent "Spent a night! Wish I could have stayed longer. The space was clean and beautifully designed, and the hotel staff were extremely accommodating to my needs. Wish I had gotten to enjoy the menu items, but I had to get back to the airport. The shuttle was also great; it came every 20 minutes, and I loved saving money on ride-sharing back to the airport in the morning. Overall great! " [](https://expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) ![Best Western Inn & Suites - Midway Airport](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/92ee0c20_y.jpg) ### Best Western Inn & Suites - Midway Airport 10/10 Excellent "Courteous staff. Clean rooms." [](https://expedia.ca/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information) ![Carlton Inn Midway](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg) ### Carlton Inn Midway 10/10 Excellent "It is a good place to stay." 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