Title: Best Bed and Breakfast South Side - £56 B&Bs in South Side | 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 [13 Feb - 15 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [6 Mar - 8 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [3 Apr - 5 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side bed & breakfast ![Private kitchen](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/662a1d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/8d057531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/4c515ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo | Balcony](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/21ce57c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sono Chicago [](https://www.expedia.co.uk/Chicago-Hotels-The-Sono-Chicago.h12913775.Hotel-Information) Near North Side 10/10 Exceptional (492 reviews) "Fantastic place! Very clean, kind and welcoming staff, great breakfast, and great location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catie £100 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/Chicago-Hotels-The-Sono-Chicago.h12913775.Hotel-Information) ![Staircase](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/5b0f48e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/86e1fd36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/fb4aa20c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/fbec7123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Publishing House B&B [](https://www.expedia.co.uk/Chicago-Hotels-The-Publishing-House-Bed-And-Breakfast.h19116049.Hotel-Information) Downtown Chicago 9.8/10 Exceptional (196 reviews) "Very clean room, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) STEVEN £137 includes taxes & fees 8 Feb - 9 Feb [](https://www.expedia.co.uk/Chicago-Hotels-The-Publishing-House-Bed-And-Breakfast.h19116049.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/cc909706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast ](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/82b0e4a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/1be0a5f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/5a018673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dorothy's [](https://www.expedia.co.uk/Chicago-Hotels-Dorothys.h108573352.Hotel-Information) Lakeview 8.4/10 Very good (105 reviews) "cozy and close to cool places" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Winter Fox £56 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Dorothys.h108573352.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/28d738d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 Bedroom (1st Floor) | Living area | 51-inch flat-screen TV with cable channels, TV, Netflix](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/f5474d0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down duvets](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/7986cc5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/e7b04404.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House 5863 - Chicago Bed and Breakfast [](https://www.expedia.co.uk/Chicago-Hotels-House-5863-Chicagos-Premier-Bed-And-Breakfast.h2792418.Hotel-Information) Edgewater 9.2/10 Wonderful (497 reviews) "Wonderful room, very good breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James £136 includes taxes & fees 8 Feb - 9 Feb [](https://www.expedia.co.uk/Chicago-Hotels-House-5863-Chicagos-Premier-Bed-And-Breakfast.h2792418.Hotel-Information) ![Double Room, Private Bathroom (Venetian) | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/8cf3a2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/bfcbb141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/7dbf8d2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/18420f50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Villa Toscana [](https://www.expedia.co.uk/Chicago-Hotels-The-Villa-Toscana.h1153874.Hotel-Information) Lakeview 7.8/10 Good (629 reviews) "Good location. Nice room. Shared bath. Excellent value. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel £57 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/Chicago-Hotels-The-Villa-Toscana.h1153874.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/2fdab583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/dd4d353d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/fe13bf55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/bfebe08d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa D' Citta [](https://www.expedia.co.uk/Chicago-Hotels-Villa-D-Citta.h22299604.Hotel-Information) Lincoln Park 9.4/10 Exceptional (114 reviews) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey £178 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Villa-D-Citta.h22299604.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/7000000/6360000/6356600/6356562/b288c54a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden Suite | Individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/7000000/6360000/6356600/6356562/79fbc793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily breakfast ](https://images.trvl-media.com/lodging/7000000/6360000/6356600/6356562/f76917c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oak Park Suite | Individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/7000000/6360000/6356600/6356562/05ff5c7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harvey House Bed & Breakfast [](https://www.expedia.co.uk/Chicago-Hotels-Harvey-House-Bed-Breakfast.h6356562.Hotel-Information) Oak Park 9.8/10 Exceptional (122 reviews) "Great hospitality. The suites have a lot of space and amenities. Beautiful location in the heart of Oak Park " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth £188 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Harvey-House-Bed-Breakfast.h6356562.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/530000/529200/529114/fd77852c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Balcony, City View (Paulina)(Facing Train – Not for Light Sleepers) | Balcony](https://images.trvl-media.com/lodging/1000000/530000/529200/529114/2b0abb94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/530000/529200/529114/4d62e2e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed | Premium bedding, desk, laptop workspace, soundproofing](https://images.trvl-media.com/lodging/1000000/530000/529200/529114/8c2ae649.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wicker Park Inn [](https://www.expedia.co.uk/Chicago-Hotels-Wicker-Park-Inn.h529114.Hotel-Information) West Town 9.0/10 Wonderful (259 reviews) "Fantastic location, spotlessly clean room, and a very comfortable bed. I have stayed here several times and will continue to do so." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey [](https://www.expedia.co.uk/Chicago-Hotels-Wicker-Park-Inn.h529114.Hotel-Information) ![Spa](https://images.trvl-media.com/lodging/19000000/18280000/18278700/18278617/6c176329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic Area](https://images.trvl-media.com/lodging/19000000/18280000/18278700/18278617/d3d95fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/19000000/18280000/18278700/18278617/67423b1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/19000000/18280000/18278700/18278617/6c529c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ray's Bucktown B&B [](https://www.expedia.co.uk/Chicago-Hotels-Rays-Bucktown-Bed-And-Breakfast.h18278617.Hotel-Information) Bucktown 9.8/10 Exceptional (388 reviews) "We had the best stay at Rays and will definitely be back! Everything about this place is fantastic, its hard to know where to begin, but the care and love put into their B&B can be felt for real. And had an unbelievably comfy and restful sleep. Woke up feeling refreshed, and had the best made to order breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristin £126 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Rays-Bucktown-Bed-And-Breakfast.h18278617.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=2026-02-21&endDate=2026-02-22®ionId=553248635074842823&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](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-Bed-And-Breakfasts.d553248635074842823-aaBedAndBreakfasts.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Bed-And-Breakfasts.d553248635074842823-aaBedAndBreakfasts.Travel-Guide-Accommodation) ## Top South Side Hotel Reviews ![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 "Staff very friendly " [](https://expedia.co.uk/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.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 "Loved it " [](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 "Great rooms With upgraded, Recently Renovated! " [](https://expedia.co.uk/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.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 "Friendly staff, clean room, quiet. " [](https://expedia.co.uk/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.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 "All great!" [](https://expedia.co.uk/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.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 "Good stay" [](https://expedia.co.uk/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Great service and clean roomd" [](https://expedia.co.uk/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Sophy Hyde Park](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f98af4f7_y.jpg) ### Sophy Hyde Park 10/10 Excellent "This is the prettiest hotel I have ever visited. Beautiful artwork throughout a very modern, clean, and friendly place. I most definitely will return!" [](https://expedia.co.uk/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) ![ LakeHouse](https://images.trvl-media.com/lodging/71000000/70890000/70886100/70886010/03d3c9c4_y.jpg) ### LakeHouse 10/10 Excellent "Enjoyed the space for a staycation, the host was very responsive in troubleshooting a booking issue. Loved the rooftop and balcony access " [](https://expedia.co.uk/Chicago-Hotels-LakeHouse.h70886010.Hotel-Information) ## Find out more about South Side ## South Side B&B information | Number of reviews | 2,579 | | ----------------- | ----- | | Accommodation | 0 B&B | | Lowest Price | £56 | | Highest Price | £188 | ## Frequently asked questions ### What is the nightly rate for a Bed and Breakfast in South Side? ### When is the best time to book a B&B in South Side? > In South Side, the peak tourist season runs from June through August, when the community comes alive with various happenings. Whether you're strolling along the riverside paths or indulging in the local culinary delights, there's plenty to keep you engaged. July, in particular, is a highlight, offering the superb balance of sun-soaked days and lively nightlife, making it an ideal time for social travellers looking to connect with others. > > > For those seeking a more budget-friendly option, visiting in December can be a wonderful choice. While the weather is cooler, often hovering around 5 to 10 degrees Celsius, this month allows you to experience South Side's festive charm without the crowds. The holiday decorations and seasonal events create a cosy atmosphere, superb for enjoying leisurely walks and intimate dining experiences. ### What is the difference between a South Side Bed and Breakfast and a hotel? ## 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) - [Bronzeville Hotels ](https://www.expedia.co.uk/Bronzeville-Chicago-Hotels.0-n6132245-0.Travel-Guide-Filter-Hotels) - 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