Title: Hillside B&B: Find the Best Bed and Breakfast from CA $136 | Expedia.ca [Hotels in Hillside](https://expedia.ca/Hillside-Hotels.d8353.Travel-Guide-Hotels)[Vacation Rentals in Hillside](https://expedia.ca/Hillside-Vacation-Rentals.d8353.Travel-Guide-VacationRentals)[Flights to Hillside](https://expedia.ca/Cheap-Flights-To-Hillside.d8353.Travel-Guide-Flights)[Hillside Car Rentals](https://expedia.ca/Car-Rentals-In-Hillside.d8353.Car-Rental-Guide)[Hillside Vacation Packages](https://expedia.ca/Hillside.d8353.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/d37ecef1eae6732579d3a923329d31ca.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Off The Beaten Track # Find a Bed and Breakfast in Hillside from CA $136 ![](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 [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Hillside B&B ![Private kitchen](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/4255bb1f.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) ![Exterior](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/28a4885f.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 (479) "Loved the shared kitchen access! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer M CA $211 CA $248 total includes taxes & fees Nov 3 - Nov 4 [](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) ![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 (186) "Wonderful staff, beautiful hotel and great breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Veronica CA $283 CA $320 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-The-Publishing-House-Bed-And-Breakfast.h19116049.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) ![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 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) ![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 Lakeview 8.4/10 Very good (89) "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 $74 CA $136 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Chicago-Hotels-Dorothys.h108573352.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) ![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) ![Garden view](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/b1dcd71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, white sand](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/0c23ce7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House 5863 - Chicago Bed and Breakfast Edgewater 9.0/10 Wonderful (488) "Super cute and comfortable place to stay. Erick was very communicative and welcoming. Great snack bar!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kirstyn CA $159 CA $263 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-House-5863-Chicagos-Premier-Bed-And-Breakfast.h2792418.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) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/527c48a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/1ea1ce86.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) ### The Villa Toscana Lakeview 7.8/10 Good (614) "Amazing location for the North Halsltead area, but also good for transport in and around the city. Uniquely weird location and place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott CA $68 CA $136 total includes taxes & fees Nov 4 - Nov 5 [](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) ![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) ![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) ### Wicker Park Inn 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) ![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 Bucktown 9.8/10 Exceptional (381) "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 $235 CA $265 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Chicago-Hotels-Rays-Bucktown-Bed-And-Breakfast.h18278617.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) ![Front of property](https://images.trvl-media.com/lodging/23000000/22300000/22299700/22299604/a2f70368.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 Lincoln Park 9.4/10 Exceptional (110) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $319 CA $375 total includes taxes & fees Nov 10 - Nov 11 [](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) ![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) ![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 Oak Park 9.8/10 Exceptional (119) "Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bethany CA $322 CA $357 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-Harvey-House-Bed-Breakfast.h6356562.Hotel-Information) ![5 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112880000/112876500/112876418/e66a2569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112880000/112876500/112876418/39f29e7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, toilet paper](https://images.trvl-media.com/lodging/113000000/112880000/112876500/112876418/7742c718.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112880000/112876500/112876418/1bdf0ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Five bedroom - 3 bath - Sleeps 12 Lakeview CA $722 CA $1,262 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Chicago-Hotels-Five-Bedroom-3-Bath-Sleeps-12.h112876418.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=2025-11-13&endDate=2025-11-14®ionId=8353&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%2FHillside-Bed-And-Breakfast.d8353-aaBedAndBreakfast.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHillside-Bed-And-Breakfast.d8353-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Hillside Hotel Reviews ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "i have been visiting chicago frequently over the last few months and this hotel thus far has exceeded any hotel stay that ive had. the staff was amazing and the location and room was great for the money spent. i will return " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![citizenM Chicago Downtown](//images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd_y.jpg) ### citizenM Chicago Downtown 10/10 Excellent "Closer parking or vale" [](https://expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.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 "Staff was very nice and the hotel is near everything " [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Sable at Navy Pier Chicago, Curio Collection by Hilton](//images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg) ### Sable at Navy Pier Chicago, Curio Collection by Hilton 10/10 Excellent "Floor-to- ceiling windows providing beautiful views of the Lake and City skyline (and windowseat) were very nice. Location was nice. Room was quiet. Bed was very comfortable. Staff was courteous and helpful." [](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "Computers need updates. Staff great." [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Great" [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![The Royal Sonesta Chicago Downtown](//images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "The only negative experience was seeing the Disgraceful Trump Tower across the street. " [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Hotel Riu Plaza Chicago](//images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg) ### Hotel Riu Plaza Chicago 10/10 Excellent "Breakfast was great, staff is always amazing. Only place I like staying in Chicago!" [](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![Pendry Chicago](//images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg) ### Pendry Chicago 10/10 Excellent "We loved the Pendry!" [](https://expedia.ca/Chicago-Hotels-Pendry-Chicago.h982552.Hotel-Information) ## Find out more about Hillside ## Hillside B&B information | Number of reviews | 2,502 | | --- | --- | | Accommodation | 32 B&B | | Lowest Price | CA $136 | | Highest Price | CA $1,262 | ## Frequently asked questions ### Searching for B&Bs in Hillside? > Whether you're on a romantic vacation and want to stay somewhere quiet, or you're traveling solo and hoping to meet fellow tourists, a B&B might be the right choice for your trip. If you're interested in playing some golf on your trip, Fresh Meadow Golf Club is a good spot to tee off. ### How do you know if a B&B is the best choice for your stay? > With attentive service, opportunities to meet guests from other places, and delectable breakfasts, B&Bs offer a unique environment. ### What are the top B&Bs in Hillside? > Below are some B&Bs in the area: [Dorothy's](https://www.expedia.ca/Chicago-Hotels-Dorothys.h108573352.Hotel-Information): 7 rooms. 13.8 mi (22.3 km) from the heart of Hillside.[House 5863 - Chicago Bed and Breakfast](https://www.expedia.ca/Chicago-Hotels-House-5863-Chicagos-Premier-Bed-And-Breakfast.h2792418.Hotel-Information): 7 rooms. 14.4 mi (23.2 km) from the downtown core. Enjoy the designer toiletries and private yard. [The Villa Toscana](https://www.expedia.ca/Chicago-Hotels-The-Villa-Toscana.h1153874.Hotel-Information): 9 rooms. Situated 13.8 mi (22.3 km) from the heart of Hillside. [The Sono Chicago](https://www.expedia.ca/Chicago-Hotels-The-Sono-Chicago.h12913775.Hotel-Information): 7 rooms. 13.6 mi (21.9 km) from the heart of downtown. Enjoy the rooftop terrace and fireplace in the lobby. [Ray's Bucktown B&B](https://www.expedia.ca/Chicago-Hotels-Rays-Bucktown-Bed-And-Breakfast.h18278617.Hotel-Information): 11 rooms. Located 11.7 mi (18.8 km) from the core of Hillside. Enjoy the free cooked breakfast and rooftop terrace. ### What's the best time of year to stay at a B&B in Hillside? > When you're dreaming of a trip to Hillside, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Hillside are January, November, February, and December, with each month seeing an average of 5 inches of snowfall. ### What is there to do in Hillside? > Travelers enjoy Hillside for its restaurants and shopping. If you want to check out some popular attractions in Hillside, you might enjoy a visit to Fresh Meadow Golf Club. Wrigley Field and Michigan Avenue are also some sites to visit if you want to see more of the area. ### How can I get to and around Hillside? > You can plan your excursions in and around Hillside ahead of time with these transportation options. Fly into Chicago O'Hare Intl. Airport (ORD), which is located 6.9 mi (11 km) away from the heart of the city. You can also search for flights into Chicago Midway Airport (MDW), which is 10.4 mi (16.7 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Vacation Rental - More ways to book - [Farmstay in Bellwood](https://www.expedia.ca/Bellwood-Agritourism.d6132079-aaAgritourism.Travel-Guide-Accommodation) - [B&B in Bellwood](https://www.expedia.ca/Bellwood-Bed-And-Breakfast.d6132079-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Golf Hotels in Bellwood](https://www.expedia.ca/Bellwood-Hotels-Golf-Hotel.0-0-d6132079-tGolfHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Bellwood](https://www.expedia.ca/Bellwood-Hotels-Spa-Hotel.0-0-d6132079-tSpaHotel.Travel-Guide-Filter-Hotels) - [Bellwood Hotels](https://www.expedia.ca/Bellwood-Hotels.d6132079.Travel-Guide-Hotels) - [Inns in Bellwood](https://www.expedia.ca/Bellwood-Inns.d6132079-aaInns.Travel-Guide-Accommodation) - [Motels in Bellwood](https://www.expedia.ca/Bellwood-Motels.d6132079-aaMotels.Travel-Guide-Accommodation) - 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