Title: Book the Best BOUTIQUE 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 Boutique Hotels Tonight [Jan 27 - Jan 28](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-27&endDate=2026-01-28&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 28 - Jan 29](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-28&endDate=2026-01-29&adults=2&propertyStyle=BOUTIQUE&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&propertyStyle=BOUTIQUE&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&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side boutique hotels ![Reception hall](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539.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/2000000/1890000/1880400/1880320/afa1818a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Magnificent)](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/53a89031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eurostars Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (3,200 reviews) "Hotel staff are nice and the rooms are clean .. This hotel is close to everything , highly recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria Rochelle CA $128 CA $151 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/220cf128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/5e20364f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/ab84c92e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/178af231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ACME Hotel Chicago, Outset Collection by Hilton [](https://www.expedia.ca/Chicago-Hotels-ACME-Hotel-Company.h886306.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (1,946 reviews) "Very convenient place to stay friendly and helpful staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rick CA $100 CA $118 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Chicago-Hotels-ACME-Hotel-Company.h886306.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/11ef5a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/fd235ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/c911ce8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Whitehall Hotel, BW Premier Collection [](https://www.expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) Downtown Chicago 8.2/10 Very good (3,912 reviews) "Location, breakfast was good, room was nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Traci CA $99 CA $116 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/b975595d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/c5557162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/85922bc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/4d55b1d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel [](https://www.expedia.ca/Chicago-Hotels-Hotel-Blake.h21142.Hotel-Information) Downtown Chicago 9.6/10 Exceptional (1,153 reviews) "Wonderful staff, close to number of attractions " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raju CA $120 CA $140 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Blake.h21142.Hotel-Information) ![Nightclub](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/6f853099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/95d7089e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/1893647b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/d0c2944a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Central Loop Hotel [](https://www.expedia.ca/Chicago-Hotels-Central-Loop-Hotel.h2151878.Hotel-Information) Downtown Chicago 8.6/10 Excellent (2,005 reviews) "Clean rooms, very friendly staff, and great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dipayan [](https://www.expedia.ca/Chicago-Hotels-Central-Loop-Hotel.h2151878.Hotel-Information) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/f57ccf79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/fa7d1870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/e1eb307d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/20c3f16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Royal Sonesta Chicago River North [](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (2,425 reviews) "Room was perfect, the staff was so friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $137 CA $205 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.Hotel-Information) ![Dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/87f941d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/48e8b586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/19985e7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/b161c307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Staypineapple, An Iconic Hotel, The Loop [](https://www.expedia.ca/Chicago-Hotels-Staypineapple.h284792.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1,006 reviews) "Location was great, staff was very friendly, and the rooms were clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori CA $122 CA $184 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Chicago-Hotels-Staypineapple.h284792.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/37fa1971.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) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/c476053d.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 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information) Downtown Chicago 7.6/10 Good (1,190 reviews) "Clean, great customer service, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arturo CA $109 CA $128 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information) ![55-inch LCD TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/bb12c333.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/325d0c28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch LCD TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/2281badb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L7 Chicago by LOTTE [](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information) Downtown Chicago 9.6/10 Exceptional (3,596 reviews) "Clean room Nice staff Great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick CA $193 CA $227 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/9c44ca76.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/6000000/5210000/5204900/5204897/612465b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/9833019f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/325381ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ivy Boutique Hotel [](https://www.expedia.ca/Chicago-Hotels-Ivy-Boutique-Hotel.h5204897.Hotel-Information) Downtown Chicago 8.6/10 Excellent (1,088 reviews) "I always stay here when in town. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $104 CA $122 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Chicago-Hotels-Ivy-Boutique-Hotel.h5204897.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=2026-02-11&endDate=2026-02-12®ionId=553248635074842823&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Great service and clean roomd" [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Cheap Hotels in Bronzeville ](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Cheap-Hotels.0-n6132245-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Bronzeville ](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Family-Hotel.0-n6132245-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bronzeville ](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Luxury-Hotel.0-n6132245-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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