Title: Hillside B&B: Find the Best Bed and Breakfast from CA $139 | 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 $139 ![](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 [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [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 two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2025-12-12&endDate=2025-12-14&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) ![Private kitchen](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/17a95121.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) ![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 Near North Side 10/10 Exceptional (479) "Loved the shared kitchen access! " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer M CA $222 CA $261 total includes taxes & fees Oct 29 - Oct 30 [](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) ![Property entrance](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/6cf646d9.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!" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Veronica CA $274 CA $310 total includes taxes & fees Oct 26 - Oct 27 [](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) ![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) ![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) ### Dorothy's Lakeview 8.4/10 Very good (83) "Clean room beautiful.yards convenient" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $87 CA $152 total includes taxes & fees Nov 11 - Nov 12 [](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) ![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) ![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) ### House 5863 - Chicago Bed and Breakfast Edgewater 9.0/10 Wonderful (486) "Super cute and comfortable place to stay. Erick was very communicative and welcoming. Great snack bar!" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Kirstyn CA $160 CA $264 total includes taxes & fees Oct 21 - Oct 22 [](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) ![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) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1160000/1153900/1153874/1ea1ce86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Villa Toscana Lakeview 7.8/10 Good (611) "Amazing location for the North Halsltead area, but also good for transport in and around the city. Uniquely weird location and place. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott CA $70 CA $139 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Chicago-Hotels-The-Villa-Toscana.h1153874.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" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $321 CA $377 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/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) ![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) ### Wicker Park Inn West Town 9.0/10 Wonderful (254) "The Wicker Park Inn is clean, beautifully decorated, and the staff is friendly and helpful!" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth R CA $289 CA $339 total includes taxes & fees Nov 17 - Nov 18 [](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) ![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) ### Ray's Bucktown B&B Bucktown 9.8/10 Exceptional (380) "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!" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Tala CA $236 CA $267 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Chicago-Hotels-Rays-Bucktown-Bed-And-Breakfast.h18278617.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) ![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) ![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 (117) "Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Bethany CA $324 CA $359 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) ![Interior](https://images.trvl-media.com/lodging/113000000/112880000/112876500/112876418/1bdf0ca4.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) ![5 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112880000/112876500/112876418/7951fd7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Five bedroom - 3 bath - Sleeps 12 Lakeview CA $820 CA $1,395 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=2025-11-01&endDate=2025-11-02®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 "Nice Staff, Cleanliness, Good location " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "I was there for the marathon and had a shared female room — the three others ended up being runners too, which was great. The location is fun and lively, but my room on the 9th floor was quiet. The staff were really nice — one of them even lent me his luck for the locker and gave me a card for the train. Very close to the start line. Amazing shopping and restaurants around. Loved it!" [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.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 "Perfect. Everything was great" [](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 "Excellent hotel, the room was large and comfortable, breakfast was great and the hotel conditions perfect " [](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![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 "Just a good place to stay " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Palmer House a Hilton Hotel](//images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Nice and convenient place. Unique atmosphere " [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Crowne Plaza Chicago West Loop by IHG](//images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg) ### Crowne Plaza Chicago West Loop by IHG 10/10 Excellent "Spent a night for our 14th anniversary. The staff was very thoughtful and kind. We appreciate the staff and room!" [](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.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 "We did the corner suite and it was amazing waking up with the sunrise over the lake. " [](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![DoubleTree by Hilton Chicago - Magnificent Mile](//images.trvl-media.com/lodging/1000000/30000/21200/21152/b1113923_y.jpg) ### DoubleTree by Hilton Chicago - Magnificent Mile 10/10 Excellent "This was perfect for Chicago Marathon. Good proximity to start and finish (about a mile) and was excellent location for spectating. " [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ## Find out more about Hillside ## Hillside B&B information | Number of reviews | 2,484 | | --- | --- | | Accommodation | 32 B&B | | Lowest Price | CA $139 | | Highest Price | CA $1,395 | ## 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. 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