Title: Book the Best BOUTIQUE Hotels in South Side in 2025 | 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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26577-Museum-Of-Science-And-Industry.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Boutique Hotels in South Side, IL ![](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 [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-26&endDate=2025-10-27&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 27 - Oct 28](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-27&endDate=2025-10-28&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side Boutique Hotels ![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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/a23482f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/c8177aa6.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) ### The Whitehall Hotel, BW Premier Collection Downtown Chicago 8.2/10 Very good (3654) "Excellent location, old style hotel with an independent feel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose CA $119 CA $140 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception hall](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/a08df61e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/5dc4c553.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eurostars Magnificent Mile Downtown Chicago 9.0/10 Wonderful (3087) "Excellent stay, close to everything and the staff was super nice " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kieata CA $151 CA $177 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/8c8ec4bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 2 Bedrooms, City View | City view](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/b54eb130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/6dd4b8c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Virgin Hotels Chicago Downtown Chicago 9.2/10 Wonderful (1395) "Excellent hotel the rooms are awesome " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Devita CA $195 CA $276 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Virgin-Hotels-Chicago.h9119528.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/20c3f16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/eaff657c.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) ### The Royal Sonesta Chicago River North Downtown Chicago 9.2/10 Wonderful (2202) "Great stay. Great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $165 CA $239 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/886bf093.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/0b4236d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; Regional cuisine ](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/b2a072ca.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) ### Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel Downtown Chicago 9.6/10 Exceptional (1046) "Love this hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $156 CA $183 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Blake.h21142.Hotel-Information) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/43ee742c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/54aa0067.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Nightclub](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/0a805224.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Single Beds](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/cf9be100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Central Loop Hotel Downtown Chicago 8.6/10 Excellent (1876) "Amazing place to stay" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jeffrey CA $136 CA $160 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Central-Loop-Hotel.h2151878.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) ![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) ![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) ![Interior entrance](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/9097f753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Felix River North/Magnificent Mile Downtown Chicago 8.2/10 Very good (2306) "Amazing stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Triston CA $97 CA $157 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.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) ![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 7.4/10 Good (1123) "Great location, spacious rooms" ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Margot CA $190 CA $224 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/12c82a23.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) ### L7 Chicago by LOTTE Downtown Chicago 9.6/10 Exceptional (3150) "This is a great location, and the staff was so friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chantelle CA $269 CA $316 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/fb6e4d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/d4c936b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/57bbec62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/a4ba0d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ACME Hotel Company Downtown Chicago 9.0/10 Wonderful (1863) "Happy with an affordable, well located, clean stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nazneen CA $150 CA $176 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-ACME-Hotel-Company.h886306.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=2025-11-09&endDate=2025-11-10®ionId=553248635074842823&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Jaslin Hotel](//images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Great hotel " [](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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