Title: Hillside Guest Houses from CA $120 | 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 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Hillside guest houses ![Exterior](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/3bf4676d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/4cdad07a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/7bc87cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/7263f497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Avenue Inn [](https://www.expedia.ca/Chicago-Hotels-Chicago-Avenue-Inn.h107226405.Hotel-Information) Humboldt Park 7.0/10 Good (101 reviews) "It was a great experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $62 CA $183 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Chicago-Hotels-Chicago-Avenue-Inn.h107226405.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/d0c2eca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/8d4eacf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, individually decorated](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/18e8c92a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/5089d88a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Dubois Guest House [](https://www.expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) Bronzeville 8.6/10 Excellent (80 reviews) "My stay was very pleasant. The accommodation was comfortable, easily accessible, and well connected to public transport. I highly recommend it to anyone visiting the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lizeth CA $103 CA $120 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/41972c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/dd3fd8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/4185cea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/0aedd339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mccormick Place Guest House [](https://www.expedia.ca/Chicago-Hotels-Mccormick-Place-Guest-House.h22670906.Hotel-Information) Bronzeville 8.8/10 Excellent (46 reviews) "Very good place,nice host " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Qiang CA $103 CA $120 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Chicago-Hotels-Mccormick-Place-Guest-House.h22670906.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=2026-02-21&endDate=2026-02-22®ionId=8353&adults=2&lodging=GUEST_HOUSE&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-Guest-Houses.d8353-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHillside-Guest-Houses.d8353-aaGuestHouses.Travel-Guide-Accommodation) ## Top Hillside Hotel Reviews ![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) ![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) ![Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/4e2c019f_y.jpg) ### Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical 10/10 Excellent "Absolutely stunning views as stated, very clean. Overall my go to place for any future stays in Chicago!" [](https://expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Downtown.h25929.Hotel-Information) ![Aloft Chicago Mag Mile](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e_y.jpg) ### Aloft Chicago Mag Mile 10/10 Excellent "it was good" [](https://expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.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 "Clean room, professional staff, and great location" [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg) ### Hotel Riu Plaza Chicago 10/10 Excellent "Nice" [](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![Holiday Inn Chicago Dwtn - The Mart by IHG](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344_y.jpg) ### Holiday Inn Chicago Dwtn - The Mart by IHG 10/10 Excellent "Some may find this hotel a little "old school", but it's dependable, clean, efficient, and well located. There are so many reviews of hotels in the downtown area that are all over the place...we went back here in 2025 after staying there in 2016, and they were on top of everything. Room could have been a tiny bit bigger, but hey, it's downtown Chicago...view was nice, room was clean and quiet, restaurant/bar area was clean and breakfast buffet was nice, and check in/out was simple. YMMV, but for \*our\* mileage, we'll always stay here when were in DT Chicago." [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information) ## Find out more about Hillside ## Hillside Guest Houses information | Number of reviews | 227 | | ----------------- | --------------- | | Accommodation | 10 Guest Houses | | Lowest Price | CA $120 | | Highest Price | CA $183 | ## 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) - 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