Title: Best Bed and Breakfast South Side - £66 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 [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) In two weeks [10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [24 Apr - 26 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [22 May - 24 May](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-05-22&endDate=2026-05-24&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side bed & breakfast ![Staircase](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/5b0f48e0.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) ![Snack bar](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/86e1fd36.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 (198 reviews) "Very clean room, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) STEVEN £159 includes taxes & fees 19 Apr - 20 Apr [](https://www.expedia.co.uk/Chicago-Hotels-The-Publishing-House-Bed-And-Breakfast.h19116049.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/662a1d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/84ce68c2.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 (497 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 £104 includes taxes & fees 6 Apr - 7 Apr [](https://www.expedia.co.uk/Chicago-Hotels-The-Sono-Chicago.h12913775.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) ![Living area](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/699f54e3.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 (110 reviews) "cozy and close to cool places" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Winter Fox £66 includes taxes & fees 29 Mar - 30 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Dorothys.h108573352.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) ![Private kitchen](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/18420f50.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/a7524278.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 (633 reviews) "Overall the stay was fantastic looking forward to booking here again in the future " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rico £76 includes taxes & fees 30 Mar - 31 Mar [](https://www.expedia.co.uk/Chicago-Hotels-The-Villa-Toscana.h1153874.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) ![Hallway](https://images.trvl-media.com/lodging/19000000/18280000/18278700/18278617/8eb960ea.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) ### 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 (394 reviews) "Best everrrrr" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew £137 includes taxes & fees 25 Mar - 26 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Rays-Bucktown-Bed-And-Breakfast.h18278617.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) ![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) ![Room, 2 Queen Beds | Egyptian cotton sheets, premium bedding, memory-foam beds, in-room safe](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/fffe1dca.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) ### Villa D' Citta [](https://www.expedia.co.uk/Chicago-Hotels-Villa-D-Citta.h22299604.Hotel-Information) Lincoln Park 9.4/10 Exceptional (115 reviews) "Everything was perfect. The food was really yummy I would love the salsa recipe. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Earl £180 includes taxes & fees 25 Mar - 26 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Villa-D-Citta.h22299604.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) ![51-inch flat-screen TV with cable channels, TV, Netflix](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/a6a881dd.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) ![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) ### 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 (499 reviews) "Wonderful room, very good breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James £159 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Chicago-Hotels-House-5863-Chicagos-Premier-Bed-And-Breakfast.h2792418.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) ![Suite, 1 King Bed | Individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/7000000/6360000/6356600/6356562/bee2290f.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) ![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 (123 reviews) "The Property was beautiful! When we walked in, the first utterance out of our mouths was "Wow!" Street parking was easy. The room "The Chalet" that we stayed in was spacious with many amenities and was spotless. The bed was very comfortable as well! And being on the third story, we got our stair steps in for our trip! Haha." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy £191 includes taxes & fees 26 Mar - 27 Mar [](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) ![Property entrance](https://images.trvl-media.com/lodging/1000000/530000/529200/529114/e9f699a6.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) ### Wicker Park Inn [](https://www.expedia.co.uk/Chicago-Hotels-Wicker-Park-Inn.h529114.Hotel-Information) West Town 9.0/10 Wonderful (261 reviews) "Everything was good." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael [](https://www.expedia.co.uk/Chicago-Hotels-Wicker-Park-Inn.h529114.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=2026-04-07&endDate=2026-04-08®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 ![Chicago Marriott Midway](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/7cf4bf83_y.jpg) ### Chicago Marriott Midway 10/10 Excellent "Great for an early morning flight from Midway on a layover with an airport shuttle. We had a great night sleep. " [](https://expedia.co.uk/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) ![Motel 6 - Chicago, IL](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/b32fc0e7_y.jpg) ### Motel 6 - Chicago, IL 10/10 Excellent "Cool" [](https://expedia.co.uk/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) ![Carlton Inn Midway](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/efb1181a_y.jpg) ### Carlton Inn Midway 4/10 Poor "El cuarto olía mucho a cigarro y según era no fumar. " [](https://expedia.co.uk/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Had a great stay " [](https://expedia.co.uk/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/d5acb403_y.jpg) ### Holiday Inn Chicago – Midway Airport S by IHG 10/10 Excellent "Great staff , enjoyed our stay , very close to where we needed to be " [](https://expedia.co.uk/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information) ![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/099e5443_y.jpg) ### Chinatown Hotel Chicago 2/10 Terrible "This was hands down the worst hotel I've ever seen. Mattress was covered in piss stains, there was puke on the computer desk, the blinds were broken, dresser was missing drawers, the bad frame was straight up made of 2x4's, and the dude at the front desk was on a personal call the entire time he was checking me in. They also offer you a free can of Coke if you give them a 10/10 review. So desperate. I'm trying to get a refund right now because we refused to stay there under such conditions. STAY AWAY FROM THIS PLACE. " [](https://expedia.co.uk/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) ![Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!](https://images.trvl-media.com/lodging/74000000/73640000/73639200/73639173/e6f80b77_y.jpg) ### Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown! 8/10 Good "Lack of amenities " [](https://expedia.co.uk/Chicago-Hotels-Comfy-4-Bedroom-Apartment-In-The-Center-Of-CHICAGO-15-Mins-From-Downtown.h73639173.Hotel-Information) ![Sophy Hyde Park](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f1fd01e1_y.jpg) ### Sophy Hyde Park 10/10 Excellent "This is my Chicago home away from home - it is beautiful " [](https://expedia.co.uk/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/e8f8e393_y.jpg) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG 8/10 Good "Bathroom extremely clean " [](https://expedia.co.uk/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) ## Find out more about South Side ## South Side B&B information | Number of reviews | 1,936 | | ----------------- | ----- | | Accommodation | 0 B&B | | Lowest Price | £66 | | Highest Price | £191 | ## 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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