Title: Chicago Vacation Home Rentals from CA $160: Search Top Private Vacation Homes for Rent | Expedia.ca [Chicago Travel Guide](https://expedia.ca/Chicago.dx178248)[Hotels in Chicago](https://expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels)[Vacation Rentals in Chicago](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Chicago Car Rentals](https://expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)[Chicago Vacation Packages](https://expedia.ca/Chicago.d178248.Destination-Travel-Guides) ![Chicago showing a high-rise building and a city as well as a family](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332049-Chicago.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Chicago Vacation Rentals ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chicago Vacation Homes ![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) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/f642030c.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) ### Stylish 1BR in West Loop Downtown Chicago 10/10 Exceptional (6) "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) ![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) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/3815ff36.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) ### 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 8 - Oct 9 [](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) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508898/5f4aabec.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/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 8 - Oct 9 [](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) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/c3fddccc.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) ### 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) ![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) ![Interior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/ed8d4a1a.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 $88 CA $276 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Chicago-Hotels-A-Quiet-Stay-While-You-Are-Away.h49092456.Hotel-Information) ![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120510000/120509000/120508906/w1187h879x8y11-002fd23e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120509000/120508906/8e2df238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120509000/120508906/055dde0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120509000/120508906/aa3b9986.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Vintage Studio in the Gold Coast Downtown Chicago CA $165 CA $318 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Chicago-Hotels-Chic-Vintage-Studio-In-The-Gold-Coast.h120508906.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) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115780000/115775200/115775130/aeb07003.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) ### Relaxing Chicago Studio Edgewater 10/10 Exceptional (17) "Had a great stay. Great location. " CA $112 CA $250 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chicago-Hotels-Relaxing-Chicago-Studio.h115775130.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) ![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) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/0523bb1b.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 15 - Oct 16 [](https://www.expedia.ca/Chicago-Hotels-Prime-City-Stay-In-A-1BR-Apt.h116793099.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793112/11a2ba3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793112/fa396607.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/117000000/116800000/116793200/116793112/56f61d6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793112/4b31f115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1BR Chic & Sunny Place Bowmanville 9.4/10 Exceptional (3) "Location was perfect for visiting family and getting around the city. Bed was extra comfy and the AC worked wonderfully. Will stay here again on our next visit. " CA $117 CA $269 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Chicago-Hotels-1BR-Chic-Sunny-Place.h116793112.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/591973f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/76fecaef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/d81d6c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/3a6b662e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Master qtr close to nature & easy urban facilities Riverwoods 9.8/10 Exceptional (67) "Beautiful, quiet space." CA $138 CA $272 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-Master-Qtr-Close-To-Nature-Easy-Urban-Facilities.h48959659.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 14 - Oct 15 [](https://www.expedia.ca/Chicago-Hotels-Chic-Studio-In-Heart-Of-Chicago.h116792702.Hotel-Information) ![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792370/77ba8bc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792370/136df166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792370/614f0803.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792370/f698a154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful 1BR Escape in Evanston South Evanston 8.0/10 Very good (5) "Quiet, clean and spacious! A peaceful neighborhood. " CA $119 CA $266 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Chicago-Hotels-Peaceful-1BR-Escape-In-Evanston.h116792370.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/117000000/116750000/116740900/116740866/f9f5b2d0.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) ![Terrace/patio](https://images.trvl-media.com/lodging/117000000/116750000/116740900/116740866/52c3cd97.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 $709 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Chicago-Hotels-4BR-Retreat-W-Theater.h116740866.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793118/9fcd9cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793118/ed48e956.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793118/eec54680.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793118/f511a20e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Great Layout – Spacious 2BR Apt Rogers Park 10/10 Exceptional (4) "Clean, comfortable, and would definitely stay again!" CA $131 CA $315 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Chicago-Hotels-2BR1BA-North-Shore-Nest.h116793118.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/e376d974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/dc90b17f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/08f64820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/b132ab29_edited_0386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed Maywood 7.8/10 Good (11) "The house was immaculate and very spacious. Beautifully decorated. The neighborhood was easy to get in and out of and close enough to downtown. Would highly recommend." CA $207 CA $330 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Chicago-Hotels-Charming-2-Bedroom-House-In-Maywood-With-WiFi.h117671933.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/bf01096c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/fd69f00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/5e34eeff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74250000/74243100/74243056/w1096h1452x0y0-f7b35f5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ✽ Charming Cottage ✽ close to College/Town/Station Wheaton 10/10 Exceptional (51) "We loved how cute this house was! It was very convenient for visiting our daughter and nice to have plenty of space and amenities. Our host was very prompt communication. Would definitely stay here again!" CA $237 CA $426 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Chicago-Hotels-Charming-Cottage-Close-To-CollegeTownStation.h74243056.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/0d5d12f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/0d56d480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/24a4685e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792547/6a360b5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Contemporary 2BR Apartment in Vibrant Hyde Park Hyde Park 10/10 Exceptional (1) "We stayed in this comfortable, quiet apartment for four weeks when my husband was undergoing radiation treatments for cancer at the University of Chicago Medical Center. It was just what we needed. The location—a block from Lake Michigan with its endless miles of parks and green spaces—was spectacular, and we spent long hours walking our dogs and biking along the lake on the beautifully landscaped walking and biking trails. The apartment itself is well appointed, clean, and blessedly quiet... CA $160 CA $346 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Chicago-Hotels-Contemporary-2BR-Apartment-In-Vibrant-Hyde-Park.h116792547.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117570000/117567100/117567072/77a14811.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/118000000/117570000/117567100/117567072/ad114d60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/118000000/117570000/117567100/117567072/950a109f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, bed sheets](https://images.trvl-media.com/lodging/118000000/117570000/117567100/117567072/4c11426e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Smart Simple and Spacious 4BR Apt State 203 Near South Side 10/10 Exceptional (4) "Great communication with Host, was exactly as described." CA $166 CA $546 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Chicago-Hotels-Smart-Simple-And-Spacious-4BR-Apt-State-203.h117567072.Hotel-Information) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792945/c9324d98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792945/f03a031d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792945/c8480aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792945/fcd2f6eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homey 1BR Space Apartment Ravenswood 9.6/10 Exceptional (7) "This was a wonderful base for the days I spent exploring Chicago. The apartment is clean and comfy and it is located right on the 'L' Brown line in a charming and vibrant neighborhood. I could zip to anywhere in the city I wanted on the L and felt very relaxed coming "home" each night." CA $100 CA $250 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chicago-Hotels-Light-Filled-1-Bedroom-Apt.h116792945.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) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117630000/117622400/117622336/9dc02038.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) ![Interior](https://images.trvl-media.com/lodging/118000000/117630000/117622400/117622336/9904f827.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 $94 CA $520 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Chicago-Hotels-2BR-Travelers-Favorite.h117622336.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=2025-10-21&endDate=2025-10-22®ionId=178248&adults=2&lodging=VACATION_HOME&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%2FChicago-Private-Vacation-Homes.d178248-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChicago-Private-Vacation-Homes.d178248-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chicago Hotel Reviews ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "Excellent location, clean and good room partners " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![The Chicago Hotel Collection - Magnificent Mile](//images.trvl-media.com/lodging/1000000/30000/21700/21619/ca00b143_y.jpg) ### The Chicago Hotel Collection - Magnificent Mile 10/10 Excellent "Walking distance from MMiles and many shops " [](https://expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information) ![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) ## Find out more about Chicago ## Chicago Vacation Homes information | Number of reviews | 51,415 | | --- | --- | | Accommodation | 842 Vacation Homes | | Lowest Price | CA $160 | | Highest Price | CA $360 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [3 Star Hotels in The Loop](https://www.expedia.ca/3Star-The-Loop-Chicago-Hotels.s30-n800024-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in The Loop](https://www.expedia.ca/4Star-The-Loop-Chicago-Hotels.s40-n800024-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in The Loop](https://www.expedia.ca/5Star-The-Loop-Chicago-Hotels.s50-n800024-0.Travel-Guide-Filter-Hotels) - 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