Title: Far Southwest Side Cottages | Expedia.ca [Far Southwest Side Travel Guide](https://expedia.ca/Far-Southwest-Side.dx553248635976475353)[Hotels in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Hotels.d553248635976475353.Travel-Guide-Hotels)[Vacation Rentals in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Vacation-Rentals.d553248635976475353.Travel-Guide-VacationRentals)[Flights to Far Southwest Side](https://expedia.ca/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights)[Far Southwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Far-Southwest-Side.d553248635976475353.Car-Rental-Guide)[Far Southwest Side Vacation Packages](https://expedia.ca/Far-Southwest-Side.d553248635976475353.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/c1b10fc2dd618159f972d6db30c06f92.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Steve Luzzo # Search Far Southwest Side Cottage Rentals ![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 In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Far Southwest Side Cottages ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93548100/93548069/2fab0d87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93548100/93548069/342b0679.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93548100/93548069/2159e545.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/94000000/93550000/93548100/93548069/6419b81c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Classic Oak Park Home, 11 Mi to Downtown Chicago! Oak Park [](https://www.expedia.ca/Chicago-Hotels-Classic-Oak-Park-Home.h93548069.Hotel-Information) ![House (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/94000000/93610000/93600500/93600477/cd8660e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93610000/93600500/93600477/ff2c0954.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93610000/93600500/93600477/e5d0b5c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93610000/93600500/93600477/b6815fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Westmont Home: Walk to Metra Station! Westmont 2.0/10 (1) "Very upset with the communication of this rental. I booked this rental for a weekend getaway with the family. I received an email a couple of days ahead of the booking reminding me of my trip and that I was all set. Then on check in day, I realized that I needed the check in information. I sent a message through the app to the renter. The response was "it may take a few days for the property to get back with you" so I called the number on the response. The operator then tried to look up my... [](https://www.expedia.ca/Chicago-Hotels-Cozy-Westmont-Home-Walk-To-Metra-Station.h93600477.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94490000/94485900/94485807/c4d10a94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94490000/94485900/94485807/6ad440f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94490000/94485900/94485807/96aa9693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94490000/94485900/94485807/deea3bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home w/ Office + Yard: 25 Mi to Downtown Chicago! Glen Ellyn [](https://www.expedia.ca/Chicago-Hotels-Home-W-Office-Yard-25-Mi-To-Downtown-Chicago.h94485807.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111920000/111911700/111911602/c37fe511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111920000/111911700/111911602/dbc3d853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111920000/111911700/111911602/228e9088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111920000/111911700/111911602/44ece33f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home w/ Fenced Yard: 13 Mi to Downtown Chicago! South Evanston [](https://www.expedia.ca/Chicago-Hotels-Home-W-Fenced-Yard-13-Mi-To-Downtown-Chicago.h111911602.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111670000/111666300/111666247/f244451a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111670000/111666300/111666247/4d8cc223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111670000/111666300/111666247/e8c4b381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111670000/111666300/111666247/0bbcc341.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4 Mi to Lake Michigan: East Chicago Home w/ Grill East Chicago [](https://www.expedia.ca/East-Chicago-Hotels-4-Mi-To-Lake-Michigan-East-Chicago-Home-W-Grill.h111666247.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/86000000/85860000/85851900/85851866/6df7627f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/86000000/85860000/85851900/85851866/0250a27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/86000000/85860000/85851900/85851866/da378a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/86000000/85860000/85851900/85851866/7d09130f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### “The cottage” 2 bedrooms cozy and private home Markham 9.4/10 Exceptional (8) "We were at this location for 13 days while visiting family. It was just what we needed for our stay. Clean and functional, enough amenities for a long stay " [](https://www.expedia.ca/Chicago-Hotels-The-Cottage-2-Bedrooms-Cozy-And-Private-Home.h85851866.Hotel-Information) ![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/94000000/93200000/93198800/93198704/19f29081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93200000/93198800/93198704/b62ee93e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93200000/93198800/93198704/147c809e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93200000/93198800/93198704/0a96b70b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park! Oak Park 10/10 Exceptional (1) "So cozy. Feels like staying in a guest house with the whole place to yourself! " [](https://www.expedia.ca/Chicago-Hotels-Charming-Oak-Park-Home-W-Private-Fire-Pit.h93198704.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/115000000/114210000/114205100/114205048/9d8c1ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/115000000/114210000/114205100/114205048/4fb31307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/115000000/114210000/114205100/114205048/ee914838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/115000000/114210000/114205100/114205048/59e1eebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Mi to Hard Rock Casino: Charming Home in Gary! Gary [](https://www.expedia.ca/Gary-Hotels-3-Mi-To-Hard-Rock-Casino-Charming-Home-In-Gary.h114205048.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/99000000/98560000/98551100/98551088/1557aead.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/99000000/98560000/98551100/98551088/7a3f79d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, laptop workspace, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/99000000/98560000/98551100/98551088/6101dbe0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Private kitchen](https://images.trvl-media.com/lodging/99000000/98560000/98551100/98551088/2dedd722.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gary Vacation Rental ~ 5 Mi to Lake Michigan! Gary [](https://www.expedia.ca/Gary-Hotels-Gary-Vacation-Rental-5-Mi-To-Lake-Michigan.h98551088.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119560000/119553200/119553167/3a4a263d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119560000/119553200/119553167/d27123e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119560000/119553200/119553167/a8b085cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119560000/119553200/119553167/67293d67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Game Room & Deck: Family Home in Chicago Area! Matteson [](https://www.expedia.ca/Matteson-Hotels-Game-Room-Deck-Family-Home-In-Chicago-Area.h119553167.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94970000/94964800/94964765/35374e29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94970000/94964800/94964765/150fcc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94970000/94964800/94964765/23fa52c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94970000/94964800/94964765/30637b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Family Glenwood Estates Home w/ Hot Tub! Glenwood [](https://www.expedia.ca/Chicago-Hotels-Spacious-Family-Glenwood-Estates-Home-W-Hot-Tub.h94964765.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=2025-10-13&endDate=2025-10-14®ionId=553248635976475353&adults=2&lodging=COTTAGE&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%2FFar-Southwest-Side-Cottages.d553248635976475353-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FFar-Southwest-Side-Cottages.d553248635976475353-aaCottages.Travel-Guide-Accommodation) ## Top Far Southwest Side Hotel Reviews ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "It was great. Juat wish there was a fridge and microwave in the room." [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.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 "Great" [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "Everything was great " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "Clean room, free wine bottle and water bottles were provided daily. Great location! Everything within 15-20 minute walk. Omar, the bartender was excellent and super friendly! Had great suggestions on where to go to eat and entertainment and made great drinks! I would stay there again and great price too! " [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![The Wade](//images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg) ### The Wade 10/10 Excellent "View was fantastic. All staff were friendly. Good location; walking distance Navy Pier." [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![Hotel Felix River North/Magnificent Mile](//images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg) ### Hotel Felix River North/Magnificent Mile 10/10 Excellent "Great location to walk to everything " [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.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 "Great hotel " [](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Aloft Chicago Mag Mile](//images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/8b47be0c_y.jpg) ### Aloft Chicago Mag Mile 10/10 Excellent "Everything was great. Will be staying again next time we come to Chicago. " [](https://expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "Excellent location. The hotel was clean and the staff were friendly. The room was very small, but we knew that when we booked. " [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ## Find out more about Far Southwest Side ## Far Southwest Side Cottages information | Number of reviews | 8 | | --- | --- | | Accommodation | 11 Cottages | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [1 Star Hotels in South Englewood](https://www.expedia.ca/1Star-South-Englewood-Chicago-Hotels.s10-n6132433-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Chatham](https://www.expedia.ca/3Star-Chatham-Chicago-Hotels.s30-n6132318-0.Travel-Guide-Filter-Hotels) - [Hotels near 95th-Dan Ryan Station](https://www.expedia.ca/95th-Dan-Ryan-Station-Hotels.d6210986.Travel-Guide-Hotels) - [Cottages in 95th Street - Longwood Station](https://www.expedia.ca/95th-Street-Longwood-Station-Cottages.d553248635996309246-aaCottages.Travel-Guide-Accommodation) - [Hotels near Abbott Park](https://www.expedia.ca/Abbott-Park-Hotels.0-l553248621555594773-0.Travel-Guide-Filter-Hotels) - 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