Title: Northwest Side Vacation Home Rentals : Search Top Private Vacation Homes for Rent | Expedia.ca ![](https://mediaim.expedia.com/destination/2/b2258a9797569cb24c44e8d88490c66c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by throwingsofas # Northwest Side Vacation 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=553248635976475367&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976475367&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976475367&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976475367&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Northwest Side Vacation Homes ![Dining](https://images.trvl-media.com/lodging/117000000/116750000/116740900/116740866/f9f5b2d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/117000000/116750000/116740900/116740866/52c3cd97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball, computer monitors](https://images.trvl-media.com/lodging/117000000/116750000/116740900/116740866/2e144bff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/117000000/116750000/116740900/116740866/4d31dd6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Theater • Game Room • Gym • Firepit • 4BR Home Belmont Cragin 7.6/10 Good (10) "Great place" CA $92 CA $710 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Chicago-Hotels-4BR-Retreat-W-Theater.h116740866.Hotel-Information) ![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/70ad4f1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/bbcd29f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/ec8e37d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/4f289e0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Prime City Stay in a 1BR Apt Irving Park 9.2/10 Wonderful (10) "Location is very good, 10 mins walk to irving blue line station, and the apartment has lot of light during the day as it was a corner unit." CA $102 CA $251 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-Prime-City-Stay-In-A-1BR-Apt.h116793099.Hotel-Information) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/7dc7e59d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/a41342cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/a0d932f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/df2ce2a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Studio in Heart of Chicago Portage Park 10/10 Exceptional (2) "Older property. Landlord special in the bathroom. Definitely needs better window coverings. Otherwise, comfortable, safe, and clean. " CA $114 CA $266 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-Chic-Studio-In-Heart-Of-Chicago.h116792702.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117470000/117469700/117469688/a31eb80f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117470000/117469700/117469688/9c89261f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117470000/117469700/117469688/3e8fa93f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117470000/117469700/117469688/1a24eeeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR • Sleeps 7 • Coffee Station • Backyard w/ Grill Belmont Cragin 8.8/10 Excellent (3) "The house was amazing. The beds were so comfortable. The stay was so fun. Thank you for everything!" CA $103 CA $533 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-2BR.h117469688.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117630000/117622400/117622336/e70556b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117630000/117622400/117622336/9904f827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/118000000/117630000/117622400/117622336/d8d5e8ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117630000/117622400/117622336/7b164128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR Traveler\`s Favorite • Modern and Clean Belmont Cragin 10/10 Exceptional (3) "Nice place and would stay here again!" CA $82 CA $504 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-2BR-Travelers-Favorite.h117622336.Hotel-Information) ![Iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792785/23205cac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792785/40915d82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792785/90c6bc63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792785/481269d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfy Studio in Portage Park- Great Value! Portage Park CA $100 CA $236 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-Comfy-Studio-In-Portage-Park-Great-Value.h116792785.Hotel-Information) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792669/bee7d697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792669/3ea06204.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792669/147b4824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792669/02976f53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2BR Apt w/ Washer & Dryer Portage Park CA $116 CA $289 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chicago-Hotels-Cozy-2BR-Apt-W-Washer-Dryer.h116792669.Hotel-Information) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792645/433bddcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792645/824ed83e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792645/ff1deed3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792645/f1329ccb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2BR Apt for a Seamless Stay Portage Park 8.0/10 Very good (1) "Everything as advertised. The only part that I was unsure of was what to do with the keys as this was not stated in any of the information provided. So I left them on the table. " CA $123 CA $297 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Chicago-Hotels-Cozy-2BR-Apt-For-A-Seamless-Stay.h116792645.Hotel-Information) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793158/bb00d0c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793158/4f19ef7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793158/efbabb04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793158/ffd7b217.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1BR Airy Apartment w/ Wi-Fi Belmont Cragin 6.0/10 (2) "The location of property was great.! Door to apt was a little complicated figuring out without key after entering code the first time .building is old you can tell with how the floors creek when you walk . Was a lot of damage inside the bathroom on Ceilings and wall like a bad water leak happened and a hole in bedroom like someone punched the wall next to the bed. The hot water did not seem to work well at all and took 20 mins just to heat up … it could use a touch up for sure and some tlc ..... CA $102 CA $251 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-1BR-Airy-Apartment-W-Wi-Fi.h116793158.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117470000/117469700/117469682/00092b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117470000/117469700/117469682/056333f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117470000/117469700/117469682/f86c3f53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/118000000/117470000/117469700/117469682/21dc5e8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR w/ Workspace + Coffee Bar • Near Transit Belmont Cragin 6.0/10 (2) "Newly refurbished apartment space was lovely! Management company was easily accessible and was very helpful. The heat of the summer kept the space a little warm (has two AC window units). " CA $82 CA $510 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-2BR-W-Workspace-Coffee-Bar-Near-Transit.h117469682.Hotel-Information) ![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792792/477cb1c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792792/3a91c960.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792792/ce22ddcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792792/a787d0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Studio in Portage Park Portage Park CA $114 CA $252 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chicago-Hotels-Cozy-Studio-In-Portage-Park.h116792792.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792649/a5b4be4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792649/5b1e5ce5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792649/0e8fe22f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792649/c7c7100f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1BR Vibrant & Inviting Apt in Chicago Portage Park 4.0/10 (1) "My impression of the property at 1st was cute.... AT 1ST! Until you see dog mess from tenants not curbing their dog. The apt is on the 2nd floor & can't use AC and other appliances unless you want a breaker blowout & waiting hours for reset. Choose another place." CA $102 CA $251 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-1BR-Vibrant-Inviting-Apt-In-Chicago.h116792649.Hotel-Information) ![8 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/118000000/117040000/117030300/117030296/4d75164f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball, table tennis](https://images.trvl-media.com/lodging/118000000/117040000/117030300/117030296/4e2244a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117040000/117030300/117030296/f2bc5faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/118000000/117040000/117030300/117030296/dcc4c24e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleeps 18 • 8BR • Game Room • Gym • Theater Portage Park 5.4/10 (3) "Great space for large groups. Park across the street is a great "feature"." CA $239 CA $1,304 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chicago-Hotels-8BR-Kids-Room.h117030296.Hotel-Information) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793114/18cda2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793114/ad056da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793114/92789d2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793114/7bc153c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1BR Gem by Shops & Dining Portage Park 2.0/10 (1) "DO NOT STAY - BEDBUGS IN THE APARTMENT. We booked for 4 nights and only stayed for 2 because there were bedbugs in the bed and we were bitten during our stay. Beware - since this is a third party property VRBO will not give you a refund. When asked about the bedbug traps they said they have never had issues, but then changed the story to say bedbugs are expected. We only saw dead ones but had bites after the 2 day stay! This was over a month ago and have not had any resolution - host will just... CA $102 CA $251 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-1BR-Gem-By-Shops-Dining.h116793114.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/3cc0a9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/89a0d93e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/9b704ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/8c87c7e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish 1BR in West Loop Downtown Chicago 10/10 Exceptional (5) "We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed" CA $128 CA $282 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Chicago-Hotels-Stylish-1BR-In-West-Loop.h116793043.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/50bbce16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/fd6dad17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/31d1cbc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/640a9e62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The One: A 1BR Stay That Feels Like Home Downtown Chicago 9.0/10 Wonderful (2) "Very nice condo in a quiet neighborhood" CA $128 CA $282 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-All-Set-Up-Furnished-1BR-Unit.h116793110.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508898/052b1dd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508898/51d75854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508898/69a5d98b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508898/be539a4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Studio Gold Coast City Living Downtown Chicago CA $128 CA $269 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-Studio-Gold-Coast-City-Living.h120508898.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/a49da56a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/6b9648de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/93c17f93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/c3fddccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sun-Drenched 1BR Apartment Downtown Chicago 10/10 Exceptional (1) "The location was fantastic. We were just a couple blocks from the Green and Pink line on Clinton. There was a code to get into the building so it felt safe. The code to the door was great because there was no key to worry about since I had to work and my hubby was in and out of the apartment all day. There were a couple small things, the bed squeaks a lot. Also, it is very clear in the listing that the train is close. It is about 30ft straight out from the window. I'm not a light sleeper so I... CA $128 CA $282 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Chicago-Hotels-Sun-Drenched-1BR-Apartment.h116792936.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/w953h720x163y0-0c76a558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/699e81d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/d1a40a0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/83dc9e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A quiet stay while you are away Oak Park 9.8/10 Exceptional (32) "We stayed a few nights and everything was nice and clean. Thank you!" CA $81 CA $269 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-A-Quiet-Stay-While-You-Are-Away.h49092456.Hotel-Information) ![Desk, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115780000/115775200/115775130/e4656d3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115780000/115775200/115775130/ec6df83e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115780000/115775200/115775130/c554d00c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115780000/115775200/115775130/d733d639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relaxing Chicago Studio Edgewater 10/10 Exceptional (17) "Had a great stay. Great location. " CA $105 CA $241 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Chicago-Hotels-Relaxing-Chicago-Studio.h115775130.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=2025-10-20&endDate=2025-10-21®ionId=553248635976475367&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Private-Vacation-Homes.d553248635976475367-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FNorthwest-Side-Private-Vacation-Homes.d553248635976475367-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Northwest Side Hotel Reviews ![Hyatt Regency Chicago](//images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "Overall nice stay. Only negative is no room service available. " [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Overall a great stay - will be saying this place for future - Thanks" [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Holiday Inn Chicago Dwtn - The Mart by IHG](//images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344_y.jpg) ### Holiday Inn Chicago Dwtn - The Mart by IHG 10/10 Excellent "This is our favorite place to stay in Chicago. Walkable to Riverwalk and other destinations. The area is clean, safe and quiet. The hotel lobby and bar are welcoming and beautiful. " [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information) ![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 "Everything was awesome. Location is excellent, shopping is nearby with plenty of restaurants. The complementary buffet breakfast is delicious." [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.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 "We stayed at The Sable last weekend and we have a serious complaint: our own home now feels deeply, deeply inadequate. The views of the city were so stunning, they ruined my ability to enjoy the view of my neighbor's fence. And the service was so fantastic, I'm now struggling to readjust to the real world. To make matters worse, the bars and restaurants downstairs were way too convenient and fun—it’s a real problem when the best spot in the city is right in your lobby. It's a dangerous place that sets unrealistic expectations for daily life. 10/10, would have my reality ruined again. " [](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![The Wade](//images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg) ### The Wade 10/10 Excellent "Dude this place was awesome the view was amazing it’s right in front of O beach, we stayed here for lollapalooza and it was a walking distance and so affordable. There’s a beautiful bar in the lobby that you can drink at and also during festivals they have pop up activations with giveaways such as aperol spritz. " [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Top Lage, sehr zentral" [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.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 "Perfect location, in walking distance to Michigan Ave, Millennium Park, Navy Pier. Friendly staff, easy check in. " [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.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 "Staff was excellent. Decor was very elegant and classy. Enjoyed my two nights here." [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ## Find out more about Northwest Side ## Northwest Side Vacation Homes information | Number of reviews | | | --- | --- | | Accommodation | Vacation Homes | | Lowest Price | | | Highest Price | | ## 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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