Title: TOP Historic Hotels in South Side, IL for 2025 | 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) ![](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) # 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 [24 Oct - 25 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-10-24&endDate=2025-10-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [25 Oct - 26 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-10-25&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [24 Oct - 26 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [31 Oct - 2 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side Historic Hotels ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/aaad0ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/8318473d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palmer House a Hilton Hotel Downtown Chicago 8.4/10 Very good (2033) "Great place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ron £112 includes taxes & fees 24 Nov - 25 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, Egyptian cotton sheets, premium bedding, down duvets](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/42397db2.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) ### InterContinental Chicago Magnificent Mile by IHG Downtown Chicago 9.0/10 Wonderful (2519) "Great location, nice rooms and excellent staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberto £182 includes taxes & fees 24 Nov - 25 Nov [](https://www.expedia.co.uk/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.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 (1025) "La Notte is an excellent restaurant on site." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary [](https://www.expedia.co.uk/Chicago-Hotels-Carleton-Of-Oak-Park.h9186.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23400/23314/6a77d719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/30000/23400/23314/f253ae17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/30000/23400/23314/8d1e22e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Lincoln Lincoln Park 7.8/10 Good (1042) "Great location and friendly staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Evan £132 includes taxes & fees 23 Nov - 24 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Hotel-Lincoln.h23314.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/w953h720x163y0-0c76a558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/ed8d4a1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/d1a40a0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/83dc9e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A quiet stay while you are away Oak Park 9.8/10 Exceptional (32) "We stayed a few nights and everything was nice and clean. Thank you!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karigan H. £147 includes taxes & fees 29 Oct - 30 Oct [](https://www.expedia.co.uk/Chicago-Hotels-A-Quiet-Stay-While-You-Are-Away.h49092456.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) ![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) ![Standard Room, 2 Queen Beds, River View | 1 bedroom, in-room safe, individually decorated, desk](https://images.trvl-media.com/lodging/16000000/15670000/15662600/15662531/ccc588cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Indigo Naperville Riverwalk by IHG Naperville 9.4/10 Exceptional (1002) "Outstanding property & stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Walter £146 includes taxes & fees 2 Nov - 3 Nov [](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/db5aefbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory-foam beds](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/66d4fb68.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) ### 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 £827 includes taxes & fees 28 Oct - 29 Oct [](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) ![Living area](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/a0078d7b.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) ### Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms Lakeview 9.0/10 Wonderful (14) "We loved the location and the VRBO itself. Clean, stocked with essentials, and easy to communicate with!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Meaghan M. £827 includes taxes & fees 28 Oct - 29 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Featured-On-The-Travel-Channel.h35179280.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/bbeef356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b5bf3aa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/f2c5642d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago Downtown Chicago 8.4/10 Very good (2264) "Staff was wonderful, property was clean and welcoming. Great amenities for families and great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen £122 includes taxes & fees 24 Nov - 25 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-Chicago.h12570.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=2025-11-07&endDate=2025-11-08®ionId=553248635074842823&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Carlton Inn Midway](//images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg) ### Carlton Inn Midway 10/10 Excellent "Very friendly! With airport shuttle!" [](https://expedia.co.uk/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) ![Hyatt Place Chicago-South/University Medical Center](//images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg) ### Hyatt Place Chicago-South/University Medical Center 10/10 Excellent "I stayed here for the Chicago marathon. It was cheaper than being closer to the start of the marathon. The staff was friendly and helpful. The property was clean. It is close to the 51st/53rd train station to be able to get to the expo at McCormick Place. Public transportation to the start of the marathon was also possible and easy. There was a Whole Foods close by. There were a few restaurants within 1 to 2 minutes outside of the door. I felt very safe walking around this area." [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Chinatown Hotel Chicago](//images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg) ### Chinatown Hotel Chicago 10/10 Excellent "Lots of affordable parking in the area and right by the red line" [](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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[Kenwood Hotels](https://www.expedia.co.uk/Kenwood-Chicago-Hotels.0-n6132343-0.Travel-Guide-Filter-Hotels) - [Hotels near Lake Meadows Park](https://www.expedia.co.uk/Lake-Meadows-Park-Hotels.0-l6132351-0.Travel-Guide-Filter-Hotels) - [Hotels near McCormick Place](https://www.expedia.co.uk/McCormick-Place-Hotels.0-l6069191-0.Travel-Guide-Filter-Hotels) - [Mckinley Park Hotels](https://www.expedia.co.uk/McKinley-Park-Chicago-Hotels.0-n6132389-0.Travel-Guide-Filter-Hotels) - [Casino Hotels in Near South Side](https://www.expedia.co.uk/Near-South-Side-Chicago-Hotels-Casino-Hotel.0-n6132399-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Near South Side Hotels](https://www.expedia.co.uk/Near-South-Side-Chicago-Hotels.0-n6132399-0.Travel-Guide-Filter-Hotels) - [Oakland Hotels](https://www.expedia.co.uk/Oakland-Chicago-Hotels.0-n6132392-0.Travel-Guide-Filter-Hotels) - [Hotels near Robert W Roloson Houses](https://www.expedia.co.uk/Robert-W-Roloson-Houses-Hotels.0-l553248621533116343-0.Travel-Guide-Filter-Hotels) - 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Peter and Paul Church](https://www.expedia.co.uk/SS-Peter-And-Paul-Church-McKinley-Park.d6247219.Attraction) - [Car hire near Lake Meadows Park](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Lake-Meadows-Park.d6132351.Car-Hire-Guide) - [Enterprise Rental Cars in Hyde Park](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Hyde-Park.d117842-c15.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in Southwest Side](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Southwest-Side.d553248635976475403-c15.Car-Rental-Guide-Suppliers) - [Europcar Rental Cars in Hyde Park](https://www.expedia.co.uk/Europcar-Car-Rentals-In-Hyde-Park.d117842-c14.Car-Rental-Guide-Suppliers) - [Book Historic Hotels in South Side on Expedia.com](https://www.expedia.com/South-Side-Hotels-Historic-Hotel.0-0-d553248635074842823-tHistoricHotel.Travel-Guide-Filter-Hotels)