Title: TOP Historic 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 Historic 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 Historic Hotels Tonight [9 Dec - 10 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-12-09&endDate=2025-12-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [10 Dec - 11 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-12-10&endDate=2025-12-11&adults=2&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&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&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side historic hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/5785af38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/fcdb86cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/89e1318d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### InterContinental Chicago Magnificent Mile by IHG Downtown Chicago 9.0/10 Wonderful (2610) "Great hotel, best location, nice and very helpful staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carlos £154 includes taxes & fees 4 Jan - 5 Jan 2026 [](https://www.expedia.co.uk/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![City view from property](https://images.trvl-media.com/lodging/1000000/30000/23400/23314/48b7272b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23400/23314/9001240a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/23400/23314/8d1e22e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23400/23314/6a77d719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Lincoln Lincoln Park 7.8/10 Good (1061) "Great " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lillian £108 includes taxes & fees 17 Dec - 18 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Hotel-Lincoln.h23314.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/10000/9200/9186/c3e40006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LCD TV](https://images.trvl-media.com/lodging/1000000/10000/9200/9186/2875d29f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 2 Double Beds | Hypo-allergenic bedding, pillow-top beds, desk, blackout curtains](https://images.trvl-media.com/lodging/1000000/10000/9200/9186/b910c9d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room | Courtyard view](https://images.trvl-media.com/lodging/1000000/10000/9200/9186/5ad45e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Carleton of Oak Park Oak Park 9.2/10 Wonderful (1005) "Spacious room, quiet night's sleep in a very pleasant historic hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward [](https://www.expedia.co.uk/Chicago-Hotels-Carleton-Of-Oak-Park.h9186.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/16000000/15670000/15662600/15662531/36353a6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15670000/15662600/15662531/a5b981a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/16000000/15670000/15662600/15662531/8ea7678b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/15670000/15662600/15662531/7b6786ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Indigo Naperville Riverwalk by IHG Naperville 9.4/10 Exceptional (1000) "Beautiful place to stay and great staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly £160 includes taxes & fees 6 Jan - 7 Jan 2026 [](https://www.expedia.co.uk/Chicago-Hotels-Hotel-Indigo-Naperville-Riverwalk.h15662531.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/59f4093c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/57dfa3ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/db5aefbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory-foam beds](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/w1055h795x5y0-32f5e83c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field Home Run 4 Bedroom, 2 Bathroom Lakeview 9.6/10 Exceptional (19) "Would definitely stay there again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Enrique £828 includes taxes & fees 11 Dec - 12 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Gorgeous-4-Bedroom-With-Pool-Table-Steps-From-Wrigley-Field-Sleeps-9.h34821849.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/3c71ed9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathroom](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/73f8ab11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory-foam beds](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/d3d80bf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/a0078d7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms Lakeview 9.0/10 Wonderful (14) "The apartment is literally across the street from the ballpark. Very clean, easy to check in, big space, everything we needed was there, couldn't have asked for more." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) vince h. £828 includes taxes & fees 11 Dec - 12 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Featured-On-The-Travel-Channel.h35179280.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=2025-12-24&endDate=2025-12-25®ionId=553248635074842823&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Carlton Inn Midway](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg) ### Carlton Inn Midway 10/10 Excellent "Staff is great, clean rooms " [](https://expedia.co.uk/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) ![Hyatt Place Chicago-South/University Medical Center](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg) ### Hyatt Place Chicago-South/University Medical Center 10/10 Excellent "Kim, at the front desk,was welcoming and helpful. She was sooooo kind and considerate!" [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg) ### Chinatown Hotel Chicago 10/10 Excellent "y" [](https://expedia.co.uk/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.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) - [Gay-Friendly Hotels in Avalon Park ](https://www.expedia.co.uk/Avalon-Park-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132379-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - 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