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) ![Chicago, IL featuring interior views and an airport as well as a couple](https://images.trvl-media.com/place/5719117/eadab43c-a88e-4198-bdcd-703715c2ebbd.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by by Midway Intl Airport # 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 [Nov 18 - Nov 19](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-11-18&endDate=2025-11-19&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 19 - Nov 20](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-11-19&endDate=2025-11-20&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-11-21&endDate=2025-11-23&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-11-28&endDate=2025-11-30&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side Boutique Hotels ![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) ![Suite (Magnificent)](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/53a89031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/e69bed89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eurostars Magnificent Mile Downtown Chicago 8.8/10 Excellent (3104) "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 $146 CA $172 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![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) ![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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/a23482f9.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 (3717) "Great stay" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jeremy CA $110 CA $129 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.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) ![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) ![Meeting facility](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/d3f07aef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Royal Sonesta Chicago River North Downtown Chicago 9.2/10 Wonderful (2255) "My favorite place to stay when I go to Chicago! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sara CA $144 CA $214 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/8c8ec4bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/49502cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Virgin Hotels Chicago Downtown Chicago 9.2/10 Wonderful (1409) "Excellent hotel the rooms are awesome " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Devita CA $171 CA $249 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Chicago-Hotels-Virgin-Hotels-Chicago.h9119528.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/1000000/10000/4200/4200/12c82a23.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) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/4d5fc313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L7 Chicago by LOTTE Downtown Chicago 9.6/10 Exceptional (3242) "Great location, comfortable hotel " ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Mark CA $215 CA $252 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.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) ![Suite, 1 Bedroom, Kitchenette (One Room)](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/d1710471.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 (1895) "Nice place with comfortable room. We enjoyed pur time there!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret CA $103 CA $121 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Chicago-Hotels-Central-Loop-Hotel.h2151878.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/c5557162.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) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/3f21eaa8.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 (1071) "Great location - perfect walking distance to main tourist areas." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexa CA $156 CA $183 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Blake.h21142.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/0ae99f9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/36bc94a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; Mediterranean cuisine, alfresco dining ](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/c8d0f7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; Mediterranean cuisine, alfresco dining ](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/1145f7d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Talbott, Autograph Collection Downtown Chicago 9.2/10 Wonderful (48) "We were there for a Bachelorette party and the hotel was at a great location for it! We could walk to so many nice restaurants and shops! The hotel staff was super friendly as well! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Baruni CA $190 CA $258 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Chicago-Hotels-The-Talbott-Hotel.h23963.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/eac2e31f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/d7b084d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch LCD TV with cable channels, iPod dock, streaming services](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/17d930ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/bfc1b4b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Staypineapple, An Iconic Hotel, The Loop Downtown Chicago 9.4/10 Exceptional (1007) "Super friendly staff and great central location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $176 CA $248 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Chicago-Hotels-Staypineapple.h284792.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/w5790h3840x5y0-fb97f2ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/w5758h3840x4y0-ff87c260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/w5109h3836x4y4-f37abf30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/w5745h3835x5y5-8bade56d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ACME Hotel Company Downtown Chicago 9.0/10 Wonderful (1880) "Love, love this hotel. Highly recommend. Excellent location, exceptional staff, room very clean. Will definitely stay here when visiting again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) stephanie CA $127 CA $149 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=2025-12-02&endDate=2025-12-03®ionId=553248635074842823&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ### Jaslin Hotel 10/10 Excellent "Clean room, walkable to restaurants and Chinatown." 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[Cheap Hotels in Kenwood](https://www.expedia.ca/Kenwood-Chicago-Hotels-Cheap-Hotels.0-n6132343-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Kenwood](https://www.expedia.ca/Kenwood-Chicago-Hotels-Luxury-Hotel.0-n6132343-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Kenwood](https://www.expedia.ca/Kenwood-Chicago-Hotels-Spa-Hotel.0-n6132343-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Kenwood Hotels](https://www.expedia.ca/Kenwood-Chicago-Hotels.0-n6132343-0.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Couples-Resorts-Hotels.0-n800025-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Romantic-Hotel.0-n800025-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Waterpark-Hotels.0-n800025-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - 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[Hotels near University of Chicago](https://www.expedia.ca/University-Of-Chicago-Hotels.0-l6064081-0.Travel-Guide-Filter-Hotels) - [Hotels near University of Chicago Medicine](https://www.expedia.ca/University-Of-Chicago-Medicine-Hotels.0-l553248635389801569-0.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-All-Inclusive-Hotel.0-n171466-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-Boutique-Hotel.0-n171466-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-Cheap-Hotels.0-n171466-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-Luxury-Hotel.0-n171466-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Washington Park Hotels](https://www.expedia.ca/Washington-Park-Chicago-Hotels.0-n171466-0.Travel-Guide-Filter-Hotels) - [Washington Park Court Hotels](https://www.expedia.ca/Washington-Park-Court-Chicago-Hotels.0-n6132200-0.Travel-Guide-Filter-Hotels) - [Hotels near Washington Park](https://www.expedia.ca/Washington-Park-Hotels.0-l507383-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Woodlawn](https://www.expedia.ca/Woodlawn-Chicago-Hotels-Cheap-Hotels.0-n6132422-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Woodlawn](https://www.expedia.ca/Woodlawn-Chicago-Hotels-Hotels-With-Indoor-Pool.0-n6132422-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Woodlawn](https://www.expedia.ca/Woodlawn-Chicago-Hotels-Luxury-Hotel.0-n6132422-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Visit Fuller Park](https://www.expedia.ca/Chicago-Fuller-Park.dx6132374) - [Visit Indian Village](https://www.expedia.ca/Chicago-Indian-Village.dx553248635976382922) - [Chicago Museum of Science and Industry](https://www.expedia.ca/Chicago-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction) - [Obama's House](https://www.expedia.ca/Obamas-House-Kenwood.d553248621533116333.Vacation-Attraction) - [Robie House](https://www.expedia.ca/Robie-House-Hyde-Park.d6064059.Vacation-Attraction) - [Car rentals near Hyde Park](https://www.expedia.ca/Car-Rentals-In-Hyde-Park.d117842.Car-Rental-Guide) - [Hertz Rental Cars in Hyde Park](https://www.expedia.ca/Hertz-Car-Rentals-In-Hyde-Park.d117842-c40.Car-Rental-Guide-Suppliers) - [Book Boutique Hotels in South Side on Expedia.com](https://www.expedia.com/South-Side-Hotels-Boutique-Hotel.0-0-d553248635074842823-tBoutiqueHotel.Travel-Guide-Filter-Hotels)