Title: Northwest Side Guest Houses from CA $122 | Expedia.ca [Northwest Side Travel Guide](https://expedia.ca/Northwest-Side.dx553248635976475367)[Hotels in Northwest Side](https://expedia.ca/Northwest-Side-Hotels.d553248635976475367.Travel-Guide-Hotels)[Vacation Rentals in Northwest Side](https://expedia.ca/Northwest-Side-Vacation-Rentals.d553248635976475367.Travel-Guide-VacationRentals)[Flights to Northwest Side](https://expedia.ca/Cheap-Flights-To-Northwest-Side.d553248635976475367.Travel-Guide-Flights)[Northwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Northwest-Side.d553248635976475367.Car-Rental-Guide)[Northwest Side Vacation Packages](https://expedia.ca/Northwest-Side.d553248635976475367.Destination-Travel-Guides) ![Bloomingdale Trail, The 606, is an elevated pedestrian trail that travels through the Bucktown and Humboldt Park neighborhoods on Chicago's northwest side. Streets of Chicago.](https://images.trvl-media.com/place/553248635976475367/bfa3a438-7753-4d4b-b110-6e23898993ba.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248635976475367/bfa3a438-7753-4d4b-b110-6e23898993ba.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 [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976475367&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976475367&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976475367&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976475367&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Northwest Side 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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/8c07545e.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) ![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) ### 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 $42 CA $158 total includes taxes & fees Jan 27 - Jan 28 [](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) ![Living area](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/994a5eaa.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) ![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) ### Villa Dubois Guest House [](https://www.expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) Bronzeville 8.8/10 Excellent (78 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 $104 CA $122 total includes taxes & fees Feb 7 - Feb 8 [](https://www.expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.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=2026-02-03&endDate=2026-02-04®ionId=553248635976475367&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%2FNorthwest-Side-Guest-Houses.d553248635976475367-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FNorthwest-Side-Guest-Houses.d553248635976475367-aaGuestHouses.Travel-Guide-Accommodation) ## Top Northwest Side Hotel Reviews ![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 "The bellman helped get me a taxi and was especially nice. " [](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 "It was great " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.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 "Room was spotless staff was wonderful and made sure everything was good and clean " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![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 "Everything is good " [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "Great staff that paid attention quickly to concerns. " [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg) ### Hotel Felix River North/Magnificent Mile 10/10 Excellent "Room was nice and clean" [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.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 "Great place to stay" [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.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 "Would definitely recommend and come back here again!" [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Courtyard by Marriott Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/529d8be8_y.jpg) ### Courtyard by Marriott Chicago Magnificent Mile 10/10 Excellent "Overall a good hotel, great central location for shopping. Front desk and valet service was exceptional! We tried the in house restaurant and unfortunately didn’t have the best experience. " [](https://expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information) ## Find out more about Northwest Side ## Northwest Side Guest Houses information | Number of reviews | 179 | | ----------------- | -------------- | | Accommodation | 5 Guest Houses | | Lowest Price | CA $122 | | Highest Price | CA $158 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [3 Star Hotels in Old Irving Park ](https://www.expedia.ca/3Star-Old-Irving-Park-Chicago-Hotels.s30-n553248635976471853-0.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Albany Park ](https://www.expedia.ca/Albany-Park-Chicago-Hotels-Luxury-Hotel.0-n6132435-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Albany Park ](https://www.expedia.ca/Albany-Park-Chicago-Hotels-Pet-Friendly-Hotel.0-n6132435-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Albany Park ](https://www.expedia.ca/Albany-Park-Chicago-Hotels-Romantic-Hotel.0-n6132435-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - 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