Title: Book the Best BOUTIQUE Hotels in Near South Side in 2025 | Expedia.ca [Near South Side Travel Guide](https://expedia.ca/Chicago-Near-South-Side.dx6132399)[Vacation Rentals in Chicago](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Near South Side Car Rentals](https://expedia.ca/Car-Rentals-In-Near-South-Side.d6132399.Car-Rental-Guide)[Near South Side Vacations](https://expedia.ca/Near-South-Side.d6132399.Destination-Travel-Guides) ![South Loop showing night scenes and street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191954-South-Loop.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Boutique Hotels in Near South Side, IL from CA $140 - ![](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 Near South Side Boutique Hotels Tonight [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-10-31&endDate=2025-11-01&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-11-01&endDate=2025-11-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Near 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) ![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) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/8750140b.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) ### The Whitehall Hotel, BW Premier Collection Downtown Chicago 8.2/10 Very good (3669) "Loved the hotel and customer service." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Whitney CA $119 CA $140 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.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) ![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) ![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 (1400) "Excellent hotel the rooms are awesome " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Devita CA $194 CA $276 total includes taxes & fees Nov 25 - Nov 26 [](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) ![Indoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/fa7d1870.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) ![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 (2212) "Great location and great staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $154 CA $225 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.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) ![1 bedroom, Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/06b28362.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 hall](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eurostars Magnificent Mile Downtown Chicago 9.0/10 Wonderful (3086) "Awesome location and excellent service, the staff was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Salvador CA $162 CA $190 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.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) ![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) ![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 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 (2327) "We had a great stay at the Felix. Kind attentive staff and excellent facilities. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Heidi CA $98 CA $158 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.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) ![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) ![Nightclub](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/0a805224.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Central Loop Hotel Downtown Chicago 8.6/10 Excellent (1876) "Friendly and helpful staff. Perfect location!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $124 CA $145 total includes taxes & fees Nov 24 - Nov 25 [](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) ![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) ![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/1000000/30000/21200/21142/0b4236d8.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 (1051) "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) ![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/bf403e2d.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) ![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 (3170) "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 $261 CA $306 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.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) ![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) ![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) ### The Chicago Hotel Collection - Magnificent Mile Downtown Chicago 7.4/10 Good (1127) "Very pleasant and helpful staff. Location was wonderful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joan CA $208 CA $244 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/a4ba0d2c.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/1000000/890000/886400/886306/884d35b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ACME Hotel Company Downtown Chicago 9.0/10 Wonderful (1878) "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=2025-11-14&endDate=2025-11-15®ionId=6132399&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Near South Side Hotel Reviews ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "i have been visiting chicago frequently over the last few months and this hotel thus far has exceeded any hotel stay that ive had. the staff was amazing and the location and room was great for the money spent. i will return " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Staff was very nice and the hotel is near everything " [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "Computers need updates. Staff great." [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![The Royal Sonesta Chicago Downtown](//images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "The only negative experience was seeing the Disgraceful Trump Tower across the street. " [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Pendry Chicago](//images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg) ### Pendry Chicago 10/10 Excellent "We loved the Pendry!" [](https://expedia.ca/Chicago-Hotels-Pendry-Chicago.h982552.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 "Staff and location" [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.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 "Staff was great, very kind and helpful. The room was great. It was clean and tidy and I enjoyed the unique decor!" [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](//images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile 10/10 Excellent "Staff is very pleasant ans friendly. Our room was on the top floor and a view that was breathtaking. " [](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ![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 "Everything was very good. Just as my previous stays have been " [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ## Frequently asked questions ### What's the best boutique accommodation in Near South Side? > [The Wheeler Mansion](https://www.expedia.ca/Chicago-Hotels-The-Wheeler-Mansion.h7818107.Hotel-Information) is a favorite hotel with our travelers looking for a stylish accommodation, and features 10 guestrooms, free breakfast, and free parking. ### What's there to see and do in Near South Side? > The scenery, lakefront, and restaurants are just some of the things to enjoy while you're in the area. Top activities and sights around Near South Side include Michigan Avenue, Navy Pier, and Wrigley Field. You might also want to see places like Soldier Field, United Center, and Arie Crown Theater during your trip. ### What's the best way to get to my boutique hotel in Near South Side? > You have a few options for transportation to and around Near South Side. The closest major airport is Chicago Midway Airport (MDW), which is located 7.9 mi (12.7 km) away, but Chicago O'Hare Intl. Airport (ORD) may also be an option. 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