Title: Hillside B&B: Find the Best Bed and Breakfast from CA $97 | 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) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Hillside bed & breakfast ![Private kitchen](https://images.trvl-media.com/lodging/13000000/12920000/12913800/12913775/662a1d77.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) ![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 [](https://www.expedia.ca/Chicago-Hotels-The-Sono-Chicago.h12913775.Hotel-Information) Near North Side 10/10 Exceptional (492 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 CA $156 CA $183 total includes taxes & fees Feb 11 - Feb 12 [](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) ![Fireplace](https://images.trvl-media.com/lodging/20000000/19120000/19116100/19116049/a2ea72ef.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.ca/Chicago-Hotels-The-Publishing-House-Bed-And-Breakfast.h19116049.Hotel-Information) Downtown Chicago 9.8/10 Exceptional (196 reviews) "Very clean room, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) STEVEN CA $263 CA $297 total includes taxes & fees Feb 28 - Mar 1 [](https://www.expedia.ca/Chicago-Hotels-The-Publishing-House-Bed-And-Breakfast.h19116049.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 WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108580000/108573400/108573352/5a018673.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) ![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) ### Dorothy's [](https://www.expedia.ca/Chicago-Hotels-Dorothys.h108573352.Hotel-Information) Lakeview 8.4/10 Very good (106 reviews) "cozy and close to cool places" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Winter Fox CA $42 CA $110 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/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/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) ### The Villa Toscana [](https://www.expedia.ca/Chicago-Hotels-The-Villa-Toscana.h1153874.Hotel-Information) Lakeview 7.8/10 Good (629 reviews) "Good location. Nice room. Shared bath. Excellent value. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $37 CA $97 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Chicago-Hotels-The-Villa-Toscana.h1153874.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) ![Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/7986cc5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 Bedroom (1st Floor) | Living area](https://images.trvl-media.com/lodging/3000000/2800000/2792500/2792418/f5474d0c.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) ### 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 (498 reviews) "Wonderful room, very good breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $145 CA $252 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Chicago-Hotels-House-5863-Chicagos-Premier-Bed-And-Breakfast.h2792418.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 King Bed](https://images.trvl-media.com/lodging/1000000/530000/529200/529114/8c2ae649.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.ca/Chicago-Hotels-Wicker-Park-Inn.h529114.Hotel-Information) West Town 9.0/10 Wonderful (259 reviews) "Fantastic location, spotlessly clean room, and a very comfortable bed. I have stayed here several times and will continue to do so." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey [](https://www.expedia.ca/Chicago-Hotels-Wicker-Park-Inn.h529114.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) ![Interior entrance](https://images.trvl-media.com/lodging/19000000/18280000/18278700/18278617/6c529c12.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) ### Ray's Bucktown B&B [](https://www.expedia.ca/Chicago-Hotels-Rays-Bucktown-Bed-And-Breakfast.h18278617.Hotel-Information) Bucktown 9.8/10 Exceptional (388 reviews) "We had the best stay at Rays and will definitely be back! Everything about this place is fantastic, its hard to know where to begin, but the care and love put into their B&B can be felt for real. And had an unbelievably comfy and restful sleep. Woke up feeling refreshed, and had the best made to order breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristin CA $207 CA $233 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/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) ![Room, 2 Queen Beds](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) ![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) ### Villa D' Citta [](https://www.expedia.ca/Chicago-Hotels-Villa-D-Citta.h22299604.Hotel-Information) Lincoln Park 9.4/10 Exceptional (114 reviews) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $279 CA $328 total includes taxes & fees Feb 16 - Feb 17 [](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) ![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 (122 reviews) "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 $313 CA $348 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Chicago-Hotels-Harvey-House-Bed-Breakfast.h6356562.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=2026-02-24&endDate=2026-02-25®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 ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "Excellent room and really great location. Stayed during the snowstorm and it was still easy to get around. Helpful friendly staff team. Note: closest EL Train station (State/Lake) closed for redevelopment till 2029\. " [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg) ### theWit Chicago, a Hilton Hotel 10/10 Excellent "Stayed at the Wit one night to see a show nearby. The hotel was busy but the staff was accommodating and wonderful, the rooftop bar was hopping and the food, drinks and sevice was great! The rooms were very clean. The State and Lake restaurant in the hotel we visited for breakfast and it has a very cool blues vibe, the food was excellent, the servers were friendly and the service was prompt! I highly recommend this hotel. " [](https://expedia.ca/Chicago-Hotels-TheWit-Chicago-A-DoubleTree-By-Hilton-Hotel.h2463437.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "Yes" [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg) ### Eurostars Magnificent Mile 10/10 Excellent "The staff was very nice. Hotel is located in a good spot so walking or the bus was sufficient. Very helpful and considerate. I would stay here again if I ever return to this city. " [](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg) ### DoubleTree by Hilton Chicago - Magnificent Mile 10/10 Excellent "Awesome quite hotel beds are amazing great location " [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg) ### LondonHouse Chicago, Curio Collection by Hilton 10/10 Excellent "Everything was amazing! View ambience service " [](https://expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Such great service, room was clean, and hotel staff were amazing! 10/10 recommend and will be staying here again when we come back!" [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Wonderful hotel" [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.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 "Yes room was spotless " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ## Find out more about Hillside ## Hillside B&B information | Number of reviews | 2,582 | | ----------------- | ------- | | Accommodation | 12 B&B | | Lowest Price | CA $97 | | Highest Price | CA $348 | ## Frequently asked questions ### Searching for B&Bs in Hillside? ### How do you know if a B&B is the best choice for your stay? ### What are the top B&Bs in Hillside? ### What's the best time of year to stay at a B&B in Hillside? ### What is there to do in Hillside? ### How can I get to and around Hillside? ## Explore a world of travel with Expedia - 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