Title: Southwest Side Condo 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 Condos 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 Next weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) 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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Southwest Side Condo Rentals ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/5bb478a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/870fb3ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/f8b770f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/e0567df2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Suite/Mins to L Train /Laundry/Free Parking Oak Park 9.6/10 Exceptional (56) "Good location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Justin C. CA $91 CA $273 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Chicago-Hotels-Chic-SuiteMins-To-L-Train-LaundryFree-Parking.h83570994.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/a067dc99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/04e27943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/6f92a1cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/e7806e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Urban Retreat Near Wrigley Field w/Parking Lakeview 10/10 Exceptional (42) "Great spot in a wonderful location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jasson R. CA $210 CA $630 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Chic-Urban-Retreat-Near-Wrigley-Field-WParking.h100783919.Hotel-Information) ![Paper towels](https://images.trvl-media.com/lodging/91000000/90900000/90893200/90893149/w1024h678x0y3-d7376dcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90900000/90893200/90893149/w1024h681x0y0-c2d7d8d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90900000/90893200/90893149/w906h683x59y0-e8bec111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/90900000/90893200/90893149/w1024h678x0y3-13685302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Just remodeled apartment close to airport and mall Elk Grove Village 10/10 Exceptional (15) "We stayed a week and found the space to be very comfortable. Just what we needed for our small family. The space was clean and well cared for and located conveniently to just about anywhere you might need to go. Host was very responsive to questions. Highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah H. CA $189 CA $356 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Just-Remodeled-Apartment-Close-To-Airport-And-Mall.h90893149.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/35000000/34920000/34913400/34913312/d68966c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom](https://images.trvl-media.com/lodging/35000000/34920000/34913400/34913312/9796e9bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathroom](https://images.trvl-media.com/lodging/35000000/34920000/34913400/34913312/e9c1d662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/35000000/34920000/34913400/34913312/d7d01a82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field MVP Suite 1 Bedroom Apartment Lakeview 9.6/10 Exceptional (14) "We found a used razer that was left in the shower and also some dishes that didn't look like they were washed. Other than those couple of things it was clean and an extremely nice stay. We went for a concert at the wrigley stadium and were able to listen to them rehearse the day before. The walk was just across the road and we were able to walk and pick up groceries from whole foods." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Clarissa CA $251 CA $934 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Inn.h34913312.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327535/b0d35ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327535/54265791.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327535/620896d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327535/fbd5e5da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Air-Conditioned King Suite | Complimentary Breakfast York Center 8.0/10 Very good (1) CA $194 CA $248 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Air-Conditioned-King-Suite-Complimentary-Breakfast.h115327535.Hotel-Information) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/117000000/116360000/116355600/116355594/4e55a309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/117000000/116360000/116355600/116355594/eae62ee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/117000000/116360000/116355600/116355594/3a8e3a3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116360000/116355600/116355594/f9745b66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious & Comfortable 3 Bedrooms + Bonus Room Forest Park 8.0/10 Very good (4) "The apartment was very clean and the beds and pillows were wey comfortable. We were close to lot of restaurants and my family. We stay again when we return..." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joy C. CA $173 CA $663 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Chicago-Hotels-Spacious-Comfortable-3-Bedrooms-Bonus-Room.h116355594.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83600000/83596200/83596157/e3a1a561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83600000/83596200/83596157/efc73b64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, offices](https://images.trvl-media.com/lodging/84000000/83600000/83596200/83596157/fd9d2968.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83600000/83596200/83596157/277a5465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 3BRCondo near Wrigley/Dtwn +FreeParking Lincoln Park 9.6/10 Exceptional (46) "Ola was an amazing host and so communicative and helpful. We loved the condo and the location. It's an amazing value for a family traveling and it was so cute and very clean. I would definitely return on my next trip back to Chicago!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kasie J. CA $296 CA $735 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Chicago-Hotels-Spacious-3BRCondo-Near-WrigleyDtwn-FreeParking.h83596157.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64620000/64617800/64617797/w917h683x48y0-6ac49149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/65000000/64620000/64617800/64617797/w905h683x60y0-f39307ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/65000000/64620000/64617800/64617797/150d1105.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/65000000/64620000/64617800/64617797/w544h683x240y0-345df6c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy One Bedroom, Washer Dryer, Central Location, Fireplace, Monthly Discounts Lombard 9.2/10 Wonderful (22) "Great apartment. Very well furnished." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dan R. CA $283 CA $494 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Comfortable-Cozy-One-Bedroom-W-Washer-Dryer.h64617797.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90130000/90125900/90125808/87bd9a01.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/91000000/90130000/90125900/90125808/8fa3e49b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90130000/90125900/90125808/fb8140c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, printers](https://images.trvl-media.com/lodging/91000000/90130000/90125900/90125808/7dd36329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking South Evanston 9.6/10 Exceptional (24) "The property was great. Clean, charming, and full of accommodations. Check in/out was really simple if you need a quick place to crash, but has everything you need for a longer stay. The best part was the communication with the host though. Very easy to get in touch with, very detailed in answering questions, and was understanding when discussing damage found from a previous guest. Overall would stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex P. CA $439 CA $882 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-MDRN-Kid-Friendly-AptCharmingPrivateSunnyFast-Wi-Fi-Parking.h90125808.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/34000000/33920000/33913000/33912904/d815e728.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms](https://images.trvl-media.com/lodging/34000000/33920000/33913000/33912904/w1055h795x5y0-8aae4c37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/34000000/33920000/33913000/33912904/8db3e70f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms](https://images.trvl-media.com/lodging/34000000/33920000/33913000/33912904/e54a5b4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom Lakeview 10/10 Exceptional (22) "This was perfect location for several of our friends to get together for the Mustache Crawl. Very clean and right in the middle of activities. The host was available and listing was accurate. We will stay again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah P. CA $672 CA $1,519 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-The-Inn-At-Wrigleyville.h33912904.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/59f4093c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory foam beds](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/w1055h795x5y0-32f5e83c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/57dfa3ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory foam beds](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/66d4fb68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field Home Run 4 Bedroom, 2 Bathroom Lakeview 9.6/10 Exceptional (19) "Steps from Wrigley. Loved it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily M. CA $672 CA $1,519 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Chicago-Hotels-Gorgeous-4-Bedroom-With-Pool-Table-Steps-From-Wrigley-Field-Sleeps-9.h34821849.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327527/9e1f9bd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327527/40eab497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327527/236e7cd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327527/9ae093ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fully-Equipped Suite | Gym Access York Center CA $194 CA $248 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Fully-Equipped-Suite-Gym-Access.h115327527.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33970000/33962200/33962122/5f4153b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/34000000/33970000/33962200/33962122/881a5b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33970000/33962200/33962122/e3135f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels](https://images.trvl-media.com/lodging/34000000/33970000/33962200/33962122/73d497c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field All Star Suite 3 Bedrooms 2 Bath Lakeview 9.4/10 Exceptional (21) "Enjoyed a dinner party with friends Place was perfect Management helpful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vince K. CA $531 CA $1,326 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Inn-AllStar-Unit.h33962122.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/35000000/34010000/34002300/34002204/15eb4dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/35000000/34010000/34002300/34002204/79e701e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/35000000/34010000/34002300/34002204/931c944e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory foam beds](https://images.trvl-media.com/lodging/35000000/34010000/34002300/34002204/c3f716d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms Lakeview 9.6/10 Exceptional (26) "It’s the perfect spot to stay for events at wrigley. Even stray kids think so ;)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebekah S. CA $672 CA $1,519 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Across-From-Wrigley-Field.h34002204.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/3c71ed9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/a0078d7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathroom](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/73f8ab11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory foam beds](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/81bc10e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms Lakeview 9.0/10 Wonderful (14) "The apartment is literally across the street from the ballpark. Very clean, easy to check in, big space, everything we needed was there, couldn't have asked for more." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) vince h. CA $672 CA $1,519 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Featured-On-The-Travel-Channel.h35179280.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/86000000/85480000/85478700/85478628/15424f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/86000000/85480000/85478700/85478628/a6354a02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/86000000/85480000/85478700/85478628/548e9e3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/86000000/85480000/85478700/85478628/106ab4fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fully-Equipped Suite | Complimentary Breakfast York Center 2.0/10 (1) "Hotel staff were great. “Suite” was a total disaster. Carpets were at least 10 years old with holes and furniture was as old and very uncomfortable. Never would have rented this “Suite” if we knew the true condition. Online pictures paint a very different picture." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul S. CA $188 CA $240 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Chicago-Hotels-Fully-Equipped-Suite-Complimentary-Breakfast.h85478628.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&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%2FSouthwest-Side-Condos.d553248635976475403-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthwest-Side-Condos.d553248635976475403-aaCondos.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 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) ### Sable at Navy Pier Chicago, Curio Collection by Hilton 10/10 Excellent "Free breakfast wasn’t offered so I don’t think it’s an option. We did a dinner boat cruise for our friend’s birthday and it was wonderful. Sable hotel is always wonderful, beautiful views from your window. The location is fun and just a great area to enjoy the weather and activities ❤️❤️💜" [](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Clean room. Super friendly front desk staff. Complimentary drinks were a big plus! Whole property was amazing. Walking distance to everything. 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