Title: Top Guest Houses in South Side in 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) ![Chicago South Side](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 prices for these dates Next weekend [6 Mar - 8 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [13 Mar - 15 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [27 Mar - 29 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [24 Apr - 26 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side guest houses ![Living area](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/41972c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-sized fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/4185cea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, memory-foam beds, individually decorated](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/c0e1e78d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/0aedd339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mccormick Place Guest House [](https://www.expedia.co.uk/Chicago-Hotels-Mccormick-Place-Guest-House.h22670906.Hotel-Information) Bronzeville 8.8/10 Excellent (46 reviews) "Very good place,nice host " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Qiang £54 includes taxes & fees 25 Feb - 26 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Mccormick-Place-Guest-House.h22670906.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/d0c2eca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/5089d88a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, individually decorated](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/18e8c92a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/994a5eaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Dubois Guest House [](https://www.expedia.co.uk/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) Bronzeville 8.6/10 Excellent (80 reviews) "My stay was very pleasant. The accommodation was comfortable, easily accessible, and well connected to public transport. I highly recommend it to anyone visiting the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lizeth £54 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/3bf4676d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/4cdad07a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/7263f497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/7bc87cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Avenue Inn [](https://www.expedia.co.uk/Chicago-Hotels-Chicago-Avenue-Inn.h107226405.Hotel-Information) Humboldt Park 7.0/10 Good (101 reviews) "It was a great experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph £106 includes taxes & fees 5 Mar - 6 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Chicago-Avenue-Inn.h107226405.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=2026-03-10&endDate=2026-03-11®ionId=553248635074842823&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AA_SPRING_PROMO_553248635074842823) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Guest-Houses.d553248635074842823-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Guest-Houses.d553248635074842823-aaGuestHouses.Travel-Guide-Accommodation) ## Top South Side Hotel Reviews ![Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!](https://images.trvl-media.com/lodging/74000000/73640000/73639200/73639173/c0eeff3c_y.jpg) ### Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown! 10/10 Excellent "I can't recommend it enough! The communication with the host was excellent throughout my stay. They were accommodating and even allowed me to stay an extra hour, which made my departure much easier. The location was perfect, and the amenities were just as described. I will definitely be returning to this rental on my next visit to Chicago!" [](https://expedia.co.uk/Chicago-Hotels-Comfy-4-Bedroom-Apartment-In-The-Center-Of-CHICAGO-15-Mins-From-Downtown.h73639173.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 "The staff is always amazing!" [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Sophy Hyde Park](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f98af4f7_y.jpg) ### Sophy Hyde Park 10/10 Excellent "Clean room. Great location for Hyde park and uchicago. " [](https://expedia.co.uk/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) ![Motel 6 - Chicago, IL](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/55e03c95_y.jpg) ### Motel 6 - Chicago, IL 10/10 Excellent "Mrs Wilson is the best" [](https://expedia.co.uk/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) ![SpringHill Suites by Marriott Chicago Chinatown](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923_y.jpg) ### SpringHill Suites by Marriott Chicago Chinatown 10/10 Excellent "Great breakfast buffet, very friendly staff, comfy beds. My roommate and I were very happy with our 12 nights here. Highly recommend. " [](https://expedia.co.uk/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.Hotel-Information) ![Best Western Inn & Suites - Midway Airport](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/92ee0c20_y.jpg) ### Best Western Inn & Suites - Midway Airport 10/10 Excellent "Clean room very nice and friendly staff member at breakfast" [](https://expedia.co.uk/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/65c30d17_y.jpg) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG 10/10 Excellent "Excellent stay" [](https://expedia.co.uk/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) ![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/w3836h2161x5y0-7f85e9e1_y.jpg) ### Holiday Inn Chicago – Midway Airport S by IHG 10/10 Excellent "Clean" [](https://expedia.co.uk/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information) ![Carlton Inn Midway](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg) ### Carlton Inn Midway 10/10 Excellent "Clean room. Professional and courteous staff" [](https://expedia.co.uk/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) ## Find out more about South Side ## South Side Guest Houses information | Number of reviews | 181 | | ----------------- | -------------- | | Accommodation | 3 Guest Houses | | Lowest Price | £54 | | Highest Price | £106 | ## 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) - [Bridgeport Hotels ](https://www.expedia.co.uk/Bridgeport-Chicago-Hotels.0-n6132075-0.Travel-Guide-Filter-Hotels) - 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