Title: Southwest Side Apartment Rentals | Expedia.ca [Southwest Side Travel Guide](https://expedia.ca/Southwest-Side.dx553248635976475403)[Hotels in Southwest Side](https://expedia.ca/Southwest-Side-Hotels.d553248635976475403.Travel-Guide-Hotels)[Vacation Rentals in Southwest Side](https://expedia.ca/Southwest-Side-Vacation-Rentals.d553248635976475403.Travel-Guide-VacationRentals)[Flights to Southwest Side](https://expedia.ca/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights)[Southwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Southwest-Side.d553248635976475403.Car-Rental-Guide)[Southwest Side Vacation Packages](https://expedia.ca/Southwest-Side.d553248635976475403.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495661-chicago-il-mdw-midway-intl.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Apartment Rentals in Southwest Side - ![](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 In two weeks [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Southwest Side Apartments ![Interior](https://images.trvl-media.com/lodging/104000000/103330000/103320500/103320435/w1349h899x1y1-aea79261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103330000/103320500/103320435/w1349h899x1y1-2d32c00d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/104000000/103330000/103320500/103320435/w1349h899x1y1-0f9df4ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103330000/103320500/103320435/w1349h899x1y1-2ba00151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10 Brighton Park 10/10 Exceptional (1) "Family-friendly, quiet, perfect for a family or friends vacationing in Chicago. The apartment is very clean and the host was always available and responded quickly. The next time I come to Chicago, i will definitely stay at the apartment \[if available\]. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fabian H. CA $104 CA $367 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Chicago-Hotels-Spacious-3-Bedroom-Apartment-10-Minutes-To-Downtown-Sleeps-Up-To-10.h103320435.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1349h899x1y1-e0042c0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1349h899x1y1-922f1c40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1350h899x0y1-7f0cda99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1350h899x0y1-24e41c53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade Brighton Park 9.0/10 Wonderful (6) "It was great it had the basic amenities for a family to enjoy the stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Damary T. CA $112 CA $378 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Chicago-Hotels-W-Pershing-Large-Chicago-Apt-3-Bed-12-Min-Downtown-Arcade.h96479287.Hotel-Information) ![Business Apartment, City View | Private kitchen](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/0374aa13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, City View](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/6a748c36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![75-inch Smart TV with digital channels, Netflix, streaming services](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/7fc927d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Apartment, City View | Living area](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/06fff62f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4BR Corporate Suite Central and Modern Near North Side 10/10 Exceptional (8) "Great location in Lincoln Park. Easy walk to several shops and restaurants. And about a 5 minute walk to the redline station (North/Clybourn). Very clean and quiet inside the unit. Building is very new. Room access through the Latch app is simple. I would definitely stay here again. The overall experience was excellent and my other guests would agree. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phillip CA $268 CA $609 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-4BR-Corporate-Suite-Central-And-Modern.h118632066.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/1309495b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/0412ba3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/f72f6088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/eab5965a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gold Coast Living: Modern Studio Unit Downtown Chicago 10/10 Exceptional (3) "Perfect pet friendly pied-à-terre! This sweet studio comes highly recommended!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandy CA $97 CA $232 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/c52efc06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/368bd483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/664fb229.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/120000000/119140000/119131900/119131874/b10cb31b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### West Loop Living – Bright 1BR Downtown Chicago 10/10 Exceptional (1) "Thorough and easy to follow parking and check in instructions. Clean apartment. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kira V. CA $101 CA $251 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-West-Loop-Living-Bright-1BR.h119131874.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/939f8498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/c1cc9a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/0ec6dac1.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/117000000/116800000/116793200/116793107/94936b9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleek 1BR Apt w/ Laundry Downtown Chicago 10/10 Exceptional (1) "I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $104 CA $255 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Chicago-Hotels-Sleek-1BR-Apt-W-Laundry.h116793107.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) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/3815ff36.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) ![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 9.4/10 Exceptional (3) "Convenient location and clean place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David S. CA $101 CA $251 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Chicago-Hotels-All-Set-Up-Furnished-1BR-Unit.h116793110.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/73f1c663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/bd271405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/a80d9e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/360842b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River North Rooftop With In and Out Parking 5 Downtown Chicago 10/10 Exceptional (2) "As advertised. Beautiful, well appointed apartment. Centrally located to restaurants, shopping and the L train. Hosts were very communicative and attentive to our needs. Highly recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike S. CA $178 CA $479 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-5.h117712536.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712527/2d716375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712527/b6735e4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712527/c67cddf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712527/d2dd93c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River North Rooftop With In and Out Parking 1 Downtown Chicago 9.0/10 Wonderful (2) "Clean rooms Adequate kitchen space Dishwasher Fast wifi with desk area to work. Near to many restaurants. Area felt safe. Communication with hosts was excellent. Minor misunderstandings resolved efficiently and completely. Beds are firm. Shower head was a little odd, almost like a strong mist and couldn't turn the showerhead to change the output. Not a real issue for me with little hair, but if you were a woman with long, thick hair, I could see it potentially being an issue. Upstairs... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan M. CA $151 CA $443 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-1.h117712527.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) ![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) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/f642030c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish 1BR in West Loop Downtown Chicago 10/10 Exceptional (9) "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" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacob D. CA $101 CA $251 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Chicago-Hotels-Stylish-1BR-In-West-Loop.h116793043.Hotel-Information) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/adbf623a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/fe11ac9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/4b4ff505.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/2e28ea21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1BR Modern Luxe Apt with In-Unit Laundry Downtown Chicago 10/10 Exceptional (1) "Great experience for me and my wife I would definitely come back " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ShowtimeFam1 CA $101 CA $251 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Chicago-Hotels-1BR-Modern-Luxe-Apt-With-In-Unit-Laundry.h119131871.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) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/003c4277.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) ![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 (2) "Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tyler B. CA $101 CA $251 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Chicago-Hotels-Sun-Drenched-1BR-Apartment.h116792936.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/42661a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/aa9373a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/21564a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/4502a11e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### South Loop Rooftop With In and Out Parking 3 Downtown Chicago 8.6/10 Excellent (4) "Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. " ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Angela M. CA $154 CA $448 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-South-Loop-Rooftop-With-In-Out-Parking.h117712525.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/e4126779.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/117000000/116800000/116793200/116793104/53fb8853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/964f82ea.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/117000000/116800000/116793200/116793104/1ab3553c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Twice as Nice: Chic 2BR Stay with Style & Space Downtown Chicago 9.6/10 Exceptional (13) "Had a very nice time in Chicago!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valerie S. CA $126 CA $310 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Chicago-Hotels-Twice-As-Nice-Chic-2BR-Stay-With-Style-Space.h116793104.Hotel-Information) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/1310976f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/c0215d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/716fc9f5.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/117000000/116800000/116792800/116792754/a190b9fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Complete 1BR Home Sum Downtown Chicago CA $101 CA $251 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-1BR-Chic-Equipped-Apt.h116792754.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/72518151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/e10fadd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/d4f07da8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/f508dbca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River North Rooftop With In and Out Parking 3 Downtown Chicago 9.4/10 Exceptional (3) "really nice place in a great location. Pretty effortless check in a and check out. It does seem you have to pay for the parking, which would have factored into my decision to choose this spot (38). I thought it was included but as we left, we were forced to pay to leave the parking lot. Also, parking is in a nearby building but really not far at all." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David S. CA $188 CA $492 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-3.h117515137.Hotel-Information) ![Smart TV, stereo](https://images.trvl-media.com/lodging/109000000/108440000/108439800/108439787/025f2d27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/109000000/108440000/108439800/108439787/12dbdb7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108440000/108439800/108439787/0d123eaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, stereo](https://images.trvl-media.com/lodging/109000000/108440000/108439800/108439787/6f85db34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pine Beam Sloth Apartment next to Blue Line Irving Park 10/10 Exceptional (4) "The place was incredible. Looks exactly as advertised. Nice neighborhood with food and coffee within walking distance. Great atmosphere! Loved my time here" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tyler S. CA $125 CA $304 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Boho-1-Bedroom-Pine-Beam-Condo-Next-To-Blue-Line.h108439787.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/w1350h899x0y1-d7005b5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, offices](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/w1350h899x0y1-19b66913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/w1350h899x0y1-beef26b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105560000/105552500/105552490/1dd62bdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Boho Chicago - 10 Minutes to Downtown Chicago Little Village 10/10 Exceptional (8) "Seriously, very beautiful place to stay like the title of the announce. Cozy and affordable!! I highly recommend if you plan to visit Chicago for a week!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Christian M. CA $93 CA $296 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Chicago-Hotels-Cozy-Boho-Chicago-10-Min-To-Chicago.h105552490.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) ![Interior](https://images.trvl-media.com/lodging/116000000/115780000/115775200/115775130/d733d639.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) ![Dining](https://images.trvl-media.com/lodging/116000000/115780000/115775200/115775130/ec6df83e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relaxing Chicago Studio Edgewater 9.8/10 Exceptional (31) "Everything was pristine and comfortable. I highly recommend this place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joyce CA $84 CA $216 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Chicago-Hotels-Relaxing-Chicago-Studio.h115775130.Hotel-Information) ![Design Apartment, Private Bathroom (The Oak Park Loft) | View from property](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/9a34c1ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design Apartment, Private Bathroom (The Oak Park Loft) | Lounge](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/6d557cee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design Apartment, Private Bathroom (The Oak Park Loft) | Lounge](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/54d73ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/fd6bd1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Oak Park Loft Oak Park 10/10 Exceptional (5) "Good location, nice neighborhood, restaurants close" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda [](https://www.expedia.ca/Chicago-Hotels-The-Oak-Park-Loft.h107622605.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=2025-11-29&endDate=2025-11-30®ionId=553248635976475403&adults=2&lodging=APARTMENT&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%2FSouthwest-Side-Apartments.d553248635976475403-aaApartments.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthwest-Side-Apartments.d553248635976475403-aaApartments.Travel-Guide-Accommodation) ## Top Southwest Side Hotel Reviews ### Hotel Riu Plaza Chicago 10/10 Excellent "Beautiful new hotel. Amazing rooms and exceptional service. Best breakfast I have had at a hotel." [](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ### Freehand Chicago 10/10 Excellent "Super friendly and helpful staff, environment felt warm and welcoming. The people who stay there are pretty cool as well! Rooms were clean and cozy. Would definitely stay there again if I’m in Chicago again." [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ### Eurostars Magnificent Mile 10/10 Excellent "The staff was so helpful and friendly!!!! " [](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ### The Wade 10/10 Excellent "Staff was welcoming! We appreciated the engineering team for stepping in and helping us out! He was kind. Would stay again! " [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ### Hotel Felix River North/Magnificent Mile 10/10 Excellent "The customer service top tier!!! The rooms were extremely small but they were clean. Staff was very helpful. " [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Centrally located by the Magnificent Mile. Plenty of shopping options. Access to both train and bus public transportation. Hotel is older but kept. Staff are friendly, efficient, abd aware of comings and goings. Always greeting you ss you leave snd return. Rooms and property are clean. Rooms are spacious for a large metro city. I have stayed at this location multiple times. Will always be my first choice. " [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ### Hilton Chicago 10/10 Excellent "It was the swankiest joint I ever strayed in! I upgraded for $40 and had a room with a view of Lake Michigan! They had three restaurants/bars right in the hotel!!" [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ### Aloft Chicago Mag Mile 10/10 Excellent "Everything was phenomenal with our stay. The staff went above and beyond to make our trip to Chicago a special one. I would recommend this hotel to ANYONE looking to visit the area. Looking forward to visiting again one day! " [](https://expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ### citizenM Chicago Downtown 10/10 Excellent "Modern, super European, petite but very " [](https://expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information) ## Find out more about Southwest Side ## Southwest Side Apartments information | Number of reviews | | | --- | --- | | Accommodation | Apartments | | 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) - [Cheap Hotels in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Cheap-Hotels.0-n6132347-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Hotels-With-Free-Parking.0-n6132347-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - 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[West Englewood Hotels](https://www.expedia.ca/West-Englewood-Chicago-Hotels.0-n6132412-0.Travel-Guide-Filter-Hotels) - [Luxury Hotels in West Lawn](https://www.expedia.ca/West-Lawn-Chicago-Hotels-Luxury-Hotel.0-n6132413-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in West Lawn](https://www.expedia.ca/West-Lawn-Chicago-Hotels-Pet-Friendly-Hotel.0-n6132413-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [West Lawn Hotels](https://www.expedia.ca/West-Lawn-Chicago-Hotels.0-n6132413-0.Travel-Guide-Filter-Hotels) - [Hotels near Zhou B Art Center](https://www.expedia.ca/Zhou-B-Art-Center-Hotels.0-l553248621533116323-0.Travel-Guide-Filter-Hotels) - [Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights from Midway Intl.](https://www.expedia.ca/lp/airports/mdw/flights-from-midway-intl-airport) - [Porter Airlines Toronto (YTZ) to Chicago (MDW) flights](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-billy-bishop-toronto-city-to-midway-intl/pd/ytz/mdw) - [Flights from Detroit (DTW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/dtw/mdw/detroit-to-chicago) - [Flights from Toronto (YTZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ywg/mdw/winnipeg-to-chicago) - [Flights from Toronto (YYZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Visit Back of the Yards](https://www.expedia.ca/Chicago-Back-Of-The-Yards.dx553248635976382392) - [Visit Brighton Park](https://www.expedia.ca/Chicago-Brighton-Park.dx6132396) - [Visit Canaryville](https://www.expedia.ca/Chicago-Canaryville.dx6132307) - [Visit Chicago Lawn](https://www.expedia.ca/Chicago-Chicago-Lawn.dx6132188) - [Visit Englewood](https://www.expedia.ca/Chicago-Englewood.dx101911) - [Visit Fuller Park](https://www.expedia.ca/Chicago-Fuller-Park.dx6132374) - [Visit Gage Park](https://www.expedia.ca/Chicago-Gage-Park.dx6132375) - [Car rentals near McKinley Park](https://www.expedia.ca/Car-Rentals-In-McKinley-Park.d6132389.Car-Rental-Guide) - [Rental cars Midway Intl. airport](https://www.expedia.ca/Car-Rentals-In-Midway-Intl.d5719117.Car-Rental-Guide) - [Book Apartments in Southwest Side on Expedia.com](https://www.expedia.com/Southwest-Side-Apartments.d553248635976475403-aaApartments.Travel-Guide-Accommodation)