Title: TOP Boutique Hotels in South Side, IL for 2026 | Expedia.co.uk [South Side Travel Guide](https://expedia.co.uk/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.co.uk/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Holiday Rentals in South Side](https://expedia.co.uk/South-Side-Holiday-Rentals.d553248635074842823.Travel-Guide-HolidayRentals)[Flights to South Side](https://expedia.co.uk/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.co.uk/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-South-Side.d553248635074842823.Car-Hire-Guide)[South Side Holidays](https://expedia.co.uk/South-Side.d553248635074842823.Holidays-City-Breaks) ![I thought Wood Ducks were the most amazingly colorful and photogenic ducks until I spotted this incredible bird on the lakefront. What a handsome beautiful duck. ](https://images.trvl-media.com/place/829/3b8962fc-94e7-486b-84ab-96e09a77459b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Richard Remington # Search Boutique Hotels in South Side - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [11 Dec - 12 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-12-11&endDate=2025-12-12&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [12 Dec - 13 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-12-12&endDate=2025-12-13&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [12 Dec - 14 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-12-12&endDate=2025-12-14&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [19 Dec - 21 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-12-19&endDate=2025-12-21&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) ![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/a08df61e.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) ![Suite (Magnificent) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/53a89031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eurostars Magnificent Mile [](https://www.expedia.co.uk/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (3144) "Great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christian £76 includes taxes & fees 11 Jan - 12 Jan 2026 [](https://www.expedia.co.uk/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![American cuisine](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/87f941d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/bbf9e380.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) ![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) ### Staypineapple, An Iconic Hotel, The Loop [](https://www.expedia.co.uk/Chicago-Hotels-Staypineapple.h284792.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1005) "Great hotel location and friendly staff! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen £103 includes taxes & fees 12 Jan - 13 Jan 2026 [](https://www.expedia.co.uk/Chicago-Hotels-Staypineapple.h284792.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/c64a9a0d.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) ### The Whitehall Hotel, BW Premier Collection [](https://www.expedia.co.uk/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) Downtown Chicago 8.2/10 Very good (3790) "Comfortable Room, great location and Excellent Staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles £67 includes taxes & fees 24 Dec - 25 Dec [](https://www.expedia.co.uk/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![55-inch LCD TV with cable channels, TV, pay films](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/bb12c333.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch LCD TV with cable channels, TV, pay films](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/2281badb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/0e6690c6.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) ### L7 Chicago by LOTTE [](https://www.expedia.co.uk/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information) Downtown Chicago 9.6/10 Exceptional (3356) "I loved the location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura £124 includes taxes & fees 3 Jan - 4 Jan 2026 [](https://www.expedia.co.uk/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/5f625b2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar, al fresco dining, open daily](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/ef1dc69e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/613c66b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/5261f576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Virgin Hotels Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Virgin-Hotels-Chicago.h9119528.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (1419) "Staff was wonderful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamie £153 includes taxes & fees 4 Jan - 5 Jan 2026 [](https://www.expedia.co.uk/Chicago-Hotels-Virgin-Hotels-Chicago.h9119528.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) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/20c3f16a.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) ![Indoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/fa7d1870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Royal Sonesta Chicago River North [](https://www.expedia.co.uk/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (2309) "Wonderful customer service, great location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle £111 includes taxes & fees 7 Jan - 8 Jan 2026 [](https://www.expedia.co.uk/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.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) ![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) ![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.co.uk/Chicago-Hotels-Hotel-Blake.h21142.Hotel-Information) Downtown Chicago 9.6/10 Exceptional (1115) "Great hotel for price and location Everything clean and a huge room " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James £83 includes taxes & fees 7 Jan - 8 Jan 2026 [](https://www.expedia.co.uk/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) ![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) ![Standard Room, 1 King Bed | Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/1893647b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Central Loop Hotel [](https://www.expedia.co.uk/Chicago-Hotels-Central-Loop-Hotel.h2151878.Hotel-Information) Downtown Chicago 8.6/10 Excellent (1928) "Great and comfortable place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olu £65 includes taxes & fees 29 Dec - 30 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Central-Loop-Hotel.h2151878.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/c6696bbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/cbdcad7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/879d69b2.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) ### The Talbott, Autograph Collection [](https://www.expedia.co.uk/Chicago-Hotels-The-Talbott-Hotel.h23963.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (59) "The location is great, always outstanding service." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yazmin £133 includes taxes & fees 28 Dec - 29 Dec [](https://www.expedia.co.uk/Chicago-Hotels-The-Talbott-Hotel.h23963.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/c35e7743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/c665b589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trump International Hotel & Tower Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1780) "Amazing hotel, location, staff, and food!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy £242 includes taxes & fees 4 Jan - 5 Jan 2026 [](https://www.expedia.co.uk/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.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.co.uk/Hotel-Search?startDate=2025-12-26&endDate=2025-12-27®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 "Excellent service, clean room, great location" [](https://expedia.co.uk/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - More ways to book - [4 Star Hotels in McKinley Park ](https://www.expedia.co.uk/4Star-McKinley-Park-Chicago-Hotels.s40-n6132389-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in New City ](https://www.expedia.co.uk/5Star-New-City-Chicago-Hotels.s50-n6132388-0.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Armour Square ](https://www.expedia.co.uk/Armour-Square-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132365-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - 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