Title: Southwest Side B&B: Find the Best Bed and Breakfast from CA $116 | Expedia.ca [Southwest Side Travel Guide](https://expedia.ca/Southwest-Side.dx553248635976475403)[Hotels in Southwest Side](https://expedia.ca/Southwest-Side-Hotels.d553248635976475403.Travel-Guide-Hotels)[Vacation Rentals in Southwest Side](https://expedia.ca/Southwest-Side-Vacation-Rentals.d553248635976475403.Travel-Guide-VacationRentals)[Flights to Southwest Side](https://expedia.ca/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights)[Southwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Southwest-Side.d553248635976475403.Car-Rental-Guide)[Southwest Side Vacation Packages](https://expedia.ca/Southwest-Side.d553248635976475403.Destination-Travel-Guides) ![Chicago, IL showing interior views, heritage elements and an airport](https://images.trvl-media.com/place/5719117/ef1b962b-07e6-469b-abf5-73ab99ceb6ee.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by by Midway Intl Airport # Find a Bed and Breakfast in Southwest Side from CA $116 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](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 [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Southwest Side bed & breakfast ![Private kitchen](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/4255bb1f.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) ![Private kitchen](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/17a95121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/28a4885f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sono Chicago [](https://www.expedia.ca/Chicago-Hotels-The-Sono-Chicago.h12913775.Hotel-Information) Near North Side 10/10 Exceptional (487) "The Sono was welcoming, clean and very comfortable. It was easy to find and provided parking! We would absolutely stay here again and would recommend it to friends. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ellen CA $180 CA $212 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/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) ![Fireplace](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/a2ea72ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/6cf646d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Publishing House B&B [](https://www.expedia.ca/Chicago-Hotels-The-Publishing-House-Bed-And-Breakfast.h19116049.Hotel-Information) Downtown Chicago 9.8/10 Exceptional (189) "Wonderful staff, beautiful hotel and great breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Veronica CA $308 CA $348 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Chicago-Hotels-The-Publishing-House-Bed-And-Breakfast.h19116049.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/cec566b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/d1d2d644.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden view](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/b1dcd71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room (Room 4)](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/8d6fe35f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House 5863 - Chicago Bed and Breakfast [](https://www.expedia.ca/Chicago-Hotels-House-5863-Chicagos-Premier-Bed-And-Breakfast.h2792418.Hotel-Information) Edgewater 9.2/10 Wonderful (497) "Nice shared spaces" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica CA $124 CA $227 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Chicago-Hotels-House-5863-Chicagos-Premier-Bed-And-Breakfast.h2792418.Hotel-Information) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/f61e991e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/422d3cbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/cc909706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, toaster oven, cookware/dishes/utensils](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/c8eee6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dorothy's [](https://www.expedia.ca/Chicago-Hotels-Dorothys.h108573352.Hotel-Information) Lakeview 8.4/10 Very good (98) "Can’t beat the price or location. Everything seemed clean and I loved the waffles. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley CA $58 CA $116 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Chicago-Hotels-Dorothys.h108573352.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) ![Oak Park Suite](https://images.trvl-media.com/lodging/7000000/6360000/6356600/6356562/05ff5c7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed](https://images.trvl-media.com/lodging/7000000/6360000/6356600/6356562/bee2290f.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) ### Harvey House Bed & Breakfast [](https://www.expedia.ca/Chicago-Hotels-Harvey-House-Bed-Breakfast.h6356562.Hotel-Information) Oak Park 9.8/10 Exceptional (121) "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 CA $316 CA $350 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Chicago-Hotels-Harvey-House-Bed-Breakfast.h6356562.Hotel-Information) ![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) ![Lounge](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/cb769b57.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) ![Exterior](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/e0aa0738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa D' Citta [](https://www.expedia.ca/Chicago-Hotels-Villa-D-Citta.h22299604.Hotel-Information) Lincoln Park 9.4/10 Exceptional (113) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $281 CA $330 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Chicago-Hotels-Villa-D-Citta.h22299604.Hotel-Information) ![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) ![Hallway](https://images.trvl-media.com/lodging/19000000/18280000/18278700/18278617/8eb960ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flamingo Room (First Floor)](https://images.trvl-media.com/lodging/19000000/18280000/18278700/18278617/38278b65.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) ### Ray's Bucktown B&B [](https://www.expedia.ca/Chicago-Hotels-Rays-Bucktown-Bed-And-Breakfast.h18278617.Hotel-Information) Bucktown 9.8/10 Exceptional (383) "Ray's is such a fun, quirky place to stay - tons of creativity has gone into making it a unique stay. The breakfast is fabulous, on-site parking is convenient, and there is excellent attention to safety and security. I thoroughly enjoyed my stay and look forward to visiting again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tala CA $216 CA $243 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Chicago-Hotels-Rays-Bucktown-Bed-And-Breakfast.h18278617.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/a7524278.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) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/527c48a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/eac88ea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Villa Toscana [](https://www.expedia.ca/Chicago-Hotels-The-Villa-Toscana.h1153874.Hotel-Information) Lakeview 7.8/10 Good (628) "Good location. Nice room. Shared bath. Excellent value. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $53 CA $117 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Chicago-Hotels-The-Villa-Toscana.h1153874.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/1000000/530000/529200/529114/b5e94ee1.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) ](https://images.trvl-media.com/lodging/1000000/530000/529200/529114/5328eeef.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/1000000/530000/529200/529114/360c6654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wicker Park Inn [](https://www.expedia.ca/Chicago-Hotels-Wicker-Park-Inn.h529114.Hotel-Information) West Town 9.0/10 Wonderful (256) "The Wicker Park Inn is clean, beautifully decorated, and the staff is friendly and helpful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth R [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2026-01-10&endDate=2026-01-11®ionId=553248635976475403&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSouthwest-Side-Bed-And-Breakfast.d553248635976475403-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthwest-Side-Bed-And-Breakfast.d553248635976475403-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Southwest Side Hotel Reviews ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Great place " [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg) ### River Hotel 10/10 Excellent "Everything was great" [](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg) ### Eurostars Magnificent Mile 10/10 Excellent "10 out of 10 will definitely be back! " [](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg) ### Club Quarters Hotel Wacker at Michigan, Chicago 10/10 Excellent "Clean room...friendly staff" [](https://expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "What a great stay!!" [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "Clean room" [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "I prefer Embassy Suite over any hotel. ES does not fail in quality, comfort, cleanliness. We enjoyed Chicago very much. Embassy Suite was in walking distance. Staff were very friendly. " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "." [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![InterContinental Chicago Magnificent Mile by IHG](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "Nice place and staff!!" [](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ## Find out more about Southwest Side ## Southwest Side B&B information | Number of reviews | 2,549 | | ----------------- | ------- | | Accommodation | 10 B&B | | Lowest Price | CA $116 | | Highest Price | CA $350 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [1 Star Hotels in South Englewood ](https://www.expedia.ca/1Star-South-Englewood-Chicago-Hotels.s10-n6132433-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Archer Heights ](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Cheap-Hotels.0-n6132347-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Archer Heights ](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Hotels-With-Free-Parking.0-n6132347-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Archer Heights ](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Romantic-Hotel.0-n6132347-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - 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