Title: Highland Park Guest Houses from CA $177 | Expedia.ca [Hotels in Highland Park](https://expedia.ca/Highland-Park-Hotels.d8345.Travel-Guide-Hotels)[Vacation Rentals in Highland Park](https://expedia.ca/Highland-Park-Vacation-Rentals.d8345.Travel-Guide-VacationRentals)[Things to do in Highland Park](https://expedia.ca/Things-To-Do-In-Highland-Park.d8345.Travel-Guide-Activities)[Highland Park Car Rentals](https://expedia.ca/Car-Rentals-In-Highland-Park.d8345.Car-Rental-Guide)[Highland Park Vacation Packages](https://expedia.ca/Highland-Park.d8345.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/ce57caea69b25748c9258315a4a459de.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Meghan hernandez # Search Guest Houses in Highland Park from CA $177 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=8345&startDate=2025-10-03&endDate=2025-10-05&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=8345&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=8345&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=8345&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Highland Park Guest Houses ![Exterior](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/f37da67a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/413d095f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/1c564c30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/19703ae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Avenue Inn Humboldt Park 7.0/10 Good (90) "It's a good place if you was traveling with a group. That way your group would get the entire floor." CA $93 CA $177 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Chicago-Hotels-Chicago-Avenue-Inn.h107226405.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/92000000/91440000/91438500/91438413/w960h1278x0y0-858a683c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment - 3rd Floor | Private kitchen](https://images.trvl-media.com/lodging/92000000/91440000/91438500/91438413/fa373d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment - 2nd Floor](https://images.trvl-media.com/lodging/92000000/91440000/91438500/91438413/e20ef351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment - 3rd Floor | Living area](https://images.trvl-media.com/lodging/92000000/91440000/91438500/91438413/0ac374cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigleyville Inn Lakeview 10/10 Exceptional (20) "The stay was amazing when going to a Chicago Cubs game! Area felt safe which is a 5 star and just a few blocks from Wrigley Field and the dining options in the area were great as well! Will definitely come back here!" CA $379 CA $645 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Inn.h91438413.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/67000000/66860000/66850900/66850874/6f6c1d8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/67000000/66860000/66850900/66850874/8971ed97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/67000000/66860000/66850900/66850874/77d7ce31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/67000000/66860000/66850900/66850874/01a499f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coach House with Heated Garage and Private Rooftop Deck Lincoln Park 9.8/10 Exceptional (17) "Awesome place to stay in Chicago. Attached garage is a huge bonus. Clean and tidy" [](https://www.expedia.ca/Chicago-Hotels-Coach-House-W-Heated-Garage-Pvt-Rooftop-Deck.h66850874.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/46000000/45820000/45812600/45812573/w906h683x60y0-2f13c280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/46000000/45820000/45812600/45812573/w906h682x60y1-0759d5ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/46000000/45820000/45812600/45812573/w904h683x61y0-89c69cfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/46000000/45820000/45812600/45812573/w947h683x39y0-14515183.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A5 Luxurious Garden Unit Near Chicago Forest Park [](https://www.expedia.ca/Chicago-Hotels-A5-Luxurious-Garden-Unit-Near-Chicago.h45812573.Hotel-Information) ![Comfort Apartment, Multiple Beds, Non Smoking | Private kitchen](https://images.trvl-media.com/lodging/29000000/28980000/28973300/28973286/3d4054b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living room](https://images.trvl-media.com/lodging/29000000/28980000/28973300/28973286/2910c3de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Apartment, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/29000000/28980000/28973300/28973286/e7b6053c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/29000000/28980000/28973300/28973286/aa473e16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wicker Park 3 Bedroom Apartment West Town [](https://www.expedia.ca/Chicago-Hotels-Wicker-Park-3-Bedroom-Apartment.h28973286.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=2025-10-07&endDate=2025-10-08®ionId=8345&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%2FHighland-Park-Guest-Houses.d8345-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHighland-Park-Guest-Houses.d8345-aaGuestHouses.Travel-Guide-Accommodation) ## Top Highland Park Hotel Reviews ![Super 8 by Wyndham Chicago O'Hare Airport](//images.trvl-media.com/lodging/1000000/450000/440500/440405/938c3a03_y.jpg) ### Super 8 by Wyndham Chicago O'Hare Airport 10/10 Excellent "Was amazing as always. This is my go to spot when staying in/near Rosemont. I see concerts at Allstate arena often and this place never fails. Staff is friendly and quick. Room is clean however it does have a slight odor. " [](https://expedia.ca/Chicago-Hotels-Super-8-By-Wyndham-Chicago-OHare-Airport.h440405.Hotel-Information) ![Claridge House](//images.trvl-media.com/lodging/1000000/30000/22700/22684/5ea33759_y.jpg) ### Claridge House 10/10 Excellent "Unique location, accomidating staff and great location. I will book again here." [](https://expedia.ca/Chicago-Hotels-Claridge-House.h22684.Hotel-Information) ![Hyatt Regency O'Hare Chicago](//images.trvl-media.com/lodging/1000000/10000/5500/5403/46cc150a_y.jpg) ### Hyatt Regency O'Hare Chicago 10/10 Excellent "Beautiful convenient property " [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-OHare-Chicago.h5403.Hotel-Information) ![The Chicago Hotel Collection River North](//images.trvl-media.com/lodging/16000000/15800000/15799700/15799614/ed2b14c2_y.jpg) ### The Chicago Hotel Collection River North 10/10 Excellent "Great property, unique and lots of communal amenities. Staff is so helpful and the rooms were basic, but exactly what we needed for our trip. You can't find many rooms for a good price that have more than one bedroom." [](https://expedia.ca/Chicago-Hotels-The-Chicago-Hotel-Collection-River-NorthMag-Mile.h15799614.Hotel-Information) ![Thompson Chicago, by Hyatt](//images.trvl-media.com/lodging/1000000/30000/26100/26076/w2559h3837x0y3-191558cd_y.jpg) ### Thompson Chicago, by Hyatt 10/10 Excellent "N" [](https://expedia.ca/Chicago-Hotels-Thompson-Chicago.h26076.Hotel-Information) ![The Chicago Hotel Collection Ambassador Gold Coast](//images.trvl-media.com/lodging/1000000/20000/17900/17809/f0cafd98_y.jpg) ### The Chicago Hotel Collection Ambassador Gold Coast 10/10 Excellent "The guess service was nice and the property was very well maintained and managed " [](https://expedia.ca/Chicago-Hotels-The-Chicago-Hotel-Collection-Ambassador-Gold-Coast.h17809.Hotel-Information) ![Holiday Inn Chicago North-Evanston by IHG](//images.trvl-media.com/lodging/1000000/10000/5400/5356/a2066909_y.jpg) ### Holiday Inn Chicago North-Evanston by IHG 10/10 Excellent "Thank you" [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-North-Evanston.h5356.Hotel-Information) ![Viceroy Chicago](//images.trvl-media.com/lodging/19000000/18620000/18614200/18614145/7bca60b9_y.jpg) ### Viceroy Chicago 10/10 Excellent "Great service and great location. Very nice and clean rooms. " [](https://expedia.ca/Chicago-Hotels-Viceroy-Chicago.h18614145.Hotel-Information) ![Hilton Chicago O'Hare Airport](//images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg) ### Hilton Chicago O'Hare Airport 10/10 Excellent "It was nice to be able to stay right at the airport when we had flown in from overseas on a long flight and then had to fly out early the next morning" [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.Hotel-Information) ## Find out more about Highland Park ## Highland Park Guest Houses information | Number of reviews | 126 | | --- | --- | | Accommodation | 5 Guest Houses | | Lowest Price | CA $177 | | Highest Price | CA $645 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Hotels with Wifi in Bannockburn](https://www.expedia.ca/Bannockburn-Chicago-Hotels-Hotel-With-Wifi.0-n601901-0-tHotelwithwifi.Travel-Guide-Filter-Hotels) - [Hyatt Hotels in Bannockburn](https://www.expedia.ca/Bannockburn-Chicago-Hotels-Hyatt-Hotels.0-n601901-0--bHyattHotels.Travel-Guide-Filter-Hotels) - 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