Title: Southwest Side B&B: Find the Best Bed and Breakfast from CA $146 | 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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495661-chicago-il-mdw-midway-intl.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find a Bed and Breakfast in Southwest Side from CA $146 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-03&endDate=2025-10-05&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Southwest Side B&B ## Our top choices for Southwest Side bed & breakfast ![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) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/43706120.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) ![Living area](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/cc909706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dorothy's Lakeview 8.4/10 Very good (76) "Clean room beautiful.yards convenient" CA $84 CA $146 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Chicago-Hotels-Dorothys.h108573352.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/eac88ea1.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) ### The Villa Toscana Lakeview 7.8/10 Good (607) "Just a wonderful tranquil oasis in such a large city and busy section of town." CA $101 CA $174 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Chicago-Hotels-The-Villa-Toscana.h1153874.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/4255bb1f.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) ![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) ### The Sono Chicago Near North Side 10/10 Exceptional (476) "Loved the shared kitchen access! " CA $322 CA $378 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Chicago-Hotels-The-Sono-Chicago.h12913775.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) ![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) ![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) ![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 Bucktown 9.8/10 Exceptional (375) "Absolutely one of the best stays I’ve ever had. " CA $239 CA $270 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Chicago-Hotels-Rays-Bucktown-Bed-And-Breakfast.h18278617.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) ![Property entrance](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/6cf646d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/73e82d38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Publishing House B&B Downtown Chicago 9.8/10 Exceptional (185) "Wonderful staff, beautiful hotel and great breakfast!" CA $293 CA $331 total includes taxes & fees Oct 6 - Oct 7 [](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) ![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) ![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) ### House 5863 - Chicago Bed and Breakfast Edgewater 9.0/10 Wonderful (481) "Everything was taken care of! A wonderful stay. " CA $167 CA $273 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Chicago-Hotels-House-5863-Chicagos-Premier-Bed-And-Breakfast.h2792418.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) ![Exclusive Apartment, 1 Queen Bed with Sofa bed (Garden) | Private kitchen](https://images.trvl-media.com/lodging/1000000/530000/529200/529114/c922ac3c.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) ![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) ### Wicker Park Inn West Town 9.0/10 Wonderful (252) "This was a great alternative to a typical hotel. The staff was extremely helpful and courteous. The room was very nice and the amenities were great. I would definitely stay again!" CA $317 CA $373 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Chicago-Hotels-Wicker-Park-Inn.h529114.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) ![Exterior](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/e0aa0738.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) ![Lounge](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/cb769b57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa D' Citta Lincoln Park 9.4/10 Exceptional (108) "Would stay again anytime!!" CA $364 CA $428 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/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) ![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](https://images.trvl-media.com/lodging/7000000/6360000/6356600/6356562/05ff5c7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/7000000/6360000/6356600/6356562/63d9fb39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harvey House Bed & Breakfast Oak Park 9.8/10 Exceptional (116) "Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast" CA $363 CA $402 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Chicago-Hotels-Harvey-House-Bed-Breakfast.h6356562.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33710000/33707400/33707372/af01555e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/34000000/33710000/33707400/33707372/aa44d57f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33710000/33707400/33707372/6196a0af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/34000000/33710000/33707400/33707372/04c50c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley! North Center 9.8/10 Exceptional (147) "Great location. Location was clean and everything was good!" [](https://www.expedia.ca/Chicago-Hotels-Deluxe-Chicago-2-Bedroom-Private-Condo-Amazing-Deal-15-Mi-From-Wrigley.h33707372.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979663/87e67293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979663/153d5a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979663/e24b64e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979663/5dbdd48e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Dubois Guest Room 6 Bronzeville CA $187 CA $327 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-Room-6.h100979663.Hotel-Information) ![TV, fireplace, books](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979643/57685b3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979643/ad3fe6b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979643/6b61d562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979643/8f7b17d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dubois Guest House Room 101 Bronzeville CA $233 CA $404 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Chicago-Hotels-Dubois-Guest-House-Room-101.h100979643.Hotel-Information) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979659/b2ac296a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979659/31ddca8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979659/3ace989b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979659/2fddd921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Dubois Guest House Room 5 Bronzeville CA $187 CA $331 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House-Room-5.h100979659.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979634/8ecf2393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979634/2567d709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979634/c79e256c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979634/7dbb46c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dubois Guest House Room 201 Bronzeville 7.4/10 Good (3) "We really enjoyed our stay. Cleanliness was top tier. " CA $233 CA $404 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Chicago-Hotels-Dubois-Guest-House-Room-201.h100979634.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979649/0c110987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979649/f9ee6228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979649/ec0fac4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979649/9a63a418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Dubois Guest House Room 2 Bronzeville CA $234 CA $402 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House-Room-2.h100979649.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979655/cef484f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979655/3f5e5b63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979655/678eb8dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979655/5f32fc1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Dubois Guest House Room 4 Bronzeville CA $234 CA $404 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House-Room-4.h100979655.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979631/499962b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979631/8d4428e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979631/efae1d52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979631/82b31ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dubois Guest House Room 202 Bronzeville 2.0/10 (1) CA $233 CA $404 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Chicago-Hotels-Dubois-Guest-House-Room-202.h100979631.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/114000000/113450000/113448200/113448187/3b852402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/114000000/113450000/113448200/113448187/7cbaacd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/114000000/113450000/113448200/113448187/aed3b8ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113450000/113448200/113448187/531f73b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigleyville Suites Room 5 Lakeview [](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Suites-Room-5.h113448187.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979647/2a6c47c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979647/de52ed8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979647/3bfedf21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100980000/100979700/100979647/4dc37092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Dubois Guest House Room 1 Bronzeville CA $280 CA $466 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House-Room-1.h100979647.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. 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[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-08&endDate=2025-10-09®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 ![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Would highly recommend this hotel. Very clean, great happy hour and awesome breakfast! Rooms are very comfortable and quiet" [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "Good room. Good location to train. Area is a little suspect" [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![The Chicago Hotel Collection - Magnificent Mile](//images.trvl-media.com/lodging/1000000/30000/21700/21619/ca00b143_y.jpg) ### The Chicago Hotel Collection - Magnificent Mile 10/10 Excellent "I loved this hotel, I really enjoyed staying there, it was a very convenient area it's close to everything. I would definitely stay there again. Thank you" [](https://expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information) ![Hyatt Regency Chicago](//images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "perfect" [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "We really enjoyed staying at the Whitehall during our Chicago visit. From the moment we stepped in, we were warmly welcomed by the staff. The room was large,clean,and the air conditioning worked great. The breakfast area was lovely and had plenty of great varieties to choose from. The location was top notch and on a quieter street. My only complaint is that the wifi connection is poor. We will likely stay again." [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "This is my third time at this hotel . Staff are so nice . Front of house, Jordan’s attention to detail in assisting me with a special request while i was here was next level . I will be back . " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Hilton Chicago](//images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "I thoroughly enjoyed my stay at the Chicago Hilton. Loved the ambiance and the inspiring architecture on entering and the old fashioned elevator lobby was a treat itself. The Irish Pub was outstanding with a nice atmosphere and not overly sports oriented like some. I was there during some kind of trade event but the place never felt crowded or had long waits for anything. My room on the 18th floor was a little spartan for my liking, though quite large, however for the amount spent I expected more. Had a nice view and was quiet enough so I’m not taking points away, but yes - a room update is past due if other rooms were like mine. " [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![River Hotel](//images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg) ### River Hotel 10/10 Excellent "Perfect for a quick weekend trip! " [](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![Hotel Felix River North/Magnificent Mile](//images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg) ### Hotel Felix River North/Magnificent Mile 10/10 Excellent "The hotel was clean, staff was friendly and helpful and great location to get to everything. I would definitely stay there again. This my 7th time ive been to" [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ## Find out more about Southwest Side ## Southwest Side B&B information | Number of reviews | 2,557 | | --- | --- | | Accommodation | 18 B&B | | Lowest Price | CA $146 | | Highest Price | CA $466 | ## 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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