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 Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Southwest Side Apartments ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1349h899x0y1-6bfcf9ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/46e46203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1280h1921x0y2-c0095f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1350h899x0y1-3830b9fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6 Brighton Park 8.6/10 Excellent (20) "Clean and nice. My son loved the arcade game. Would stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nichole S. CA $98 CA $298 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Chicago-Hotels-Sunflower-Apt-12-Min-From-Downtown-CHI.h91086437.Hotel-Information) ![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/bdb082e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/8c33e770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/1309495b.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) ### Cozy Gold Coast Studio Stay Downtown Chicago 10/10 Exceptional (1) "The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Seynabou CA $136 CA $283 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.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, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/640a9e62.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) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/3815ff36.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" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Patrick CA $126 CA $286 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chicago-Hotels-All-Set-Up-Furnished-1BR-Unit.h116793110.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) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/61009377.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) ![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 9.4/10 Exceptional (10) "Had a very nice time in Chicago!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valerie S. CA $137 CA $325 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chicago-Hotels-Twice-As-Nice-Chic-2BR-Stay-With-Style-Space.h116793104.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) ![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b754723c.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) ### West Loop Living – Bright 1BR Downtown Chicago CA $136 CA $294 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Chicago-Hotels-West-Loop-Living-Bright-1BR.h119131874.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) ![Exterior detail](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712527/c67cddf3.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) ![Interior](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712527/4b557c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River North Rooftop With In and Out Parking 1 Downtown Chicago 10/10 Exceptional (1) "Awesome location, great place would definitely recommend will hopefully return" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) lucas c. CA $157 CA $458 total includes taxes & fees Nov 19 - Nov 20 [](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/117000000/116800000/116793000/116792936/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) ![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) ### 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... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer A. CA $129 CA $286 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Chicago-Hotels-Sun-Drenched-1BR-Apartment.h116792936.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/73f1c663.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) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/5da8154a.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) ### River North Rooftop With In and Out Parking 5 Downtown Chicago 10/10 Exceptional (2) "Everything was amazing, property was even better than expected" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacob CA $188 CA $499 total includes taxes & fees Oct 29 - Oct 30 [](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/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) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/9b704ea8.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) ### Stylish 1BR in West Loop Downtown Chicago 10/10 Exceptional (7) "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 $136 CA $297 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chicago-Hotels-Stylish-1BR-In-West-Loop.h116793043.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/96000000/95660000/95650200/95650151/71dd56c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95660000/95650200/95650151/f52d9a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis](https://images.trvl-media.com/lodging/96000000/95660000/95650200/95650151/9e37fc30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95660000/95650200/95650151/786103ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Your Chicago get Away Downtown Chicago 8.4/10 Very good (6) "Clean, fun space and responsive host! Loved the views from our room!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tyler C. CA $263 CA $562 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Chicago-Hotels-Your-Chicago-Get-Away.h95650151.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) ![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) ![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/96789a75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1BR Modern Luxe Apt with In-Unit Laundry Downtown Chicago CA $133 CA $294 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-1BR-Modern-Luxe-Apt-With-In-Unit-Laundry.h119131871.Hotel-Information) ![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/88e6ca50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/d96cd2bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/b4e6230b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/961b149c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### South Loop Rooftop With In and Out Parking 3 Downtown Chicago 7.0/10 Good (2) "Really nice location and place. Only issue was some confusion with the parking " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cora C. CA $201 CA $516 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Chicago-Hotels-South-Loop-Rooftop-With-In-Out-Parking.h117712525.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) ![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) ### Relaxing Chicago Studio Edgewater 9.8/10 Exceptional (25) "Had a great stay. Great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Justin CA $91 CA $225 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chicago-Hotels-Relaxing-Chicago-Studio.h115775130.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) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/0ec6dac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/a9804ae4.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) ### 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 $126 CA $286 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chicago-Hotels-Sleek-1BR-Apt-W-Laundry.h116793107.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) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/2bfb9517.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) ![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) ### Complete 1BR Home Sum Downtown Chicago CA $136 CA $292 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Chicago-Hotels-1BR-Chic-Equipped-Apt.h116792754.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/121000000/120510000/120509000/120508906/055dde0c.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) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/121000000/120510000/120509000/120508906/9fc64539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Vintage Studio in the Gold Coast Downtown Chicago CA $136 CA $283 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Chicago-Hotels-Chic-Vintage-Studio-In-The-Gold-Coast.h120508906.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 $129 CA $273 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chicago-Hotels-Studio-Gold-Coast-City-Living.h120508898.Hotel-Information) ![Apartment, Private Bathroom | Terrace/patio](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/2e2b5c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, Private Bathroom | Shared kitchen](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/7a41f6a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, Private Bathroom | Exterior](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/9734bd4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, Private Bathroom](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/b9d0f86f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### At Home in Oak Park Oak Park 9.4/10 Exceptional (8) "Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathryn CA $207 CA $373 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Chicago-Hotels-Home-In-Oak-Park.h75609586.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712540/794407f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712540/e784e67e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712540/e515c1d8.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/118000000/117720000/117712600/117712540/e370a9b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River North Rooftop With In and Out Parking 6 Downtown Chicago 8.0/10 Very good (1) "Location was extremely ideal. Staff very responsive. All the apartments were very clean. The pictures were very accurate to what you can expect" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) john Z. CA $215 CA $534 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-6.h117712540.Hotel-Information) ![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/121000000/120510000/120509000/120508914/05e7d3f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120510000/120509000/120508914/w960h1024x64y0-b440b3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120510000/120509000/120508914/w1192h800x0y0-e7fc2f0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/121000000/120510000/120509000/120508914/84a01e59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1BR Gold Coast Vintage Gem Downtown Chicago CA $133 CA $296 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chicago-Hotels-1BR-Gold-Coast-Vintage-Gem.h120508914.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=2025-11-05&endDate=2025-11-06®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](//images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg) ### Hotel Riu Plaza Chicago 10/10 Excellent "fresh breakfast attentive and pleasant staff" [](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![Palmer House a Hilton Hotel](//images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Very clean and welcoming. " [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "Love the live jazz and vibe in the cafe and cocktail lounge. Overall, as expected for an upscale youth hostel. " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.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 "Parking was terrible and expensive. Recommend valet parking. Staff, very hard to talk to and i arrived at 3:30 scheduled to check in at 4 pm. Room wasn't available until 4;30. Staff wasn't to concerned." [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Nice location, rooms were nice size beds were comfortable water pressure was great " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.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 "Location, location, location" [](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![The Royal Sonesta Chicago Downtown](//images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "The room was great, view gorgeous and all the hotel staff were welcoming and helpful! Location of the hotel is perfect to walk or take the metro. The restaurant had limited choices for breakfast but was nice enough and convenient." [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](//images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile 10/10 Excellent "It was affordable " [](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.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 "It was a beautiful property in a spectacular location. Close to transit, and walkable to everything in the loop. Would definitely stay again. " [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.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) - [Romantic Hotels in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Romantic-Hotel.0-n6132347-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Archer Heights Hotels](https://www.expedia.ca/Archer-Heights-Chicago-Hotels.0-n6132347-0.Travel-Guide-Filter-Hotels) - [Hotels near Ashland-63rd Station](https://www.expedia.ca/Ashland-63rd-Station-Hotels.d6211065.Travel-Guide-Hotels) - [Hotels near Bridgeport Art Center](https://www.expedia.ca/Bridgeport-Art-Center-Hotels.0-l553248621533116324-0.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Brighton Park](https://www.expedia.ca/Brighton-Park-Chicago-Hotels-Boutique-Hotel.0-n6132396-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Brighton Park](https://www.expedia.ca/Brighton-Park-Chicago-Hotels-Cheap-Hotels.0-n6132396-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Brighton Park Hotels](https://www.expedia.ca/Brighton-Park-Chicago-Hotels.0-n6132396-0.Travel-Guide-Filter-Hotels) - [Canaryville Hotels](https://www.expedia.ca/Canaryville-Chicago-Hotels.0-n6132307-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Cermak-Chinatown Station](https://www.expedia.ca/Cermak-Chinatown-Station-Apart-Hotels.d6210889-aaApartHotels.Travel-Guide-Accommodation) - [Aparthotels in Chicago 35th Street-Lou Jones-Bronzeville Station](https://www.expedia.ca/Chicago-35th-Street-Lou-Jones-Bronzeville-Station-Apart-Hotels.d6213376-aaApartHotels.Travel-Guide-Accommodation) - [Chalets in Chicago 35th Street-Lou Jones-Bronzeville Station](https://www.expedia.ca/Chicago-35th-Street-Lou-Jones-Bronzeville-Station-Chalets.d6213376-aaChalets.Travel-Guide-Accommodation) - [Inns in Chicago 35th Street-Lou Jones-Bronzeville Station](https://www.expedia.ca/Chicago-35th-Street-Lou-Jones-Bronzeville-Station-Inns.d6213376-aaInns.Travel-Guide-Accommodation) - [Resorts in Chicago 35th Street-Lou Jones-Bronzeville Station](https://www.expedia.ca/Chicago-35th-Street-Lou-Jones-Bronzeville-Station-Resort-Hotels.d6213376-aaResortHotels.Travel-Guide-Accommodation) - [B&B in Chicago 47th Street Station](https://www.expedia.ca/Chicago-47th-Street-Station-Bed-And-Breakfast.d6212783-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Chicago 51st-53rd Street Station](https://www.expedia.ca/Chicago-51st-53rd-Street-Station-Guest-Houses.d6212787-aaGuestHouses.Travel-Guide-Accommodation) - [Resorts in Chicago 51st-53rd Street Station](https://www.expedia.ca/Chicago-51st-53rd-Street-Station-Resort-Hotels.d6212787-aaResortHotels.Travel-Guide-Accommodation) - [Guest Houses in Chicago 55th-56th-57th Street Station](https://www.expedia.ca/Chicago-55th-56th-57th-Street-Station-Guest-Houses.d6212797-aaGuestHouses.Travel-Guide-Accommodation) - [Resorts in Chicago 55th-56th-57th Street Station](https://www.expedia.ca/Chicago-55th-56th-57th-Street-Station-Resort-Hotels.d6212797-aaResortHotels.Travel-Guide-Accommodation) - [Inns in Chicago 59th Street Station](https://www.expedia.ca/Chicago-59th-Street-Station-Inns.d6212800-aaInns.Travel-Guide-Accommodation) - [Guest Houses in Chicago 63rd Street Station](https://www.expedia.ca/Chicago-63rd-Street-Station-Guest-Houses.d6212802-aaGuestHouses.Travel-Guide-Accommodation) - [Inns in Chicago Halsted Station](https://www.expedia.ca/Chicago-Halsted-Station-Inns.d6213464-aaInns.Travel-Guide-Accommodation) - [Resorts in Chicago Halsted Station](https://www.expedia.ca/Chicago-Halsted-Station-Resort-Hotels.d6213464-aaResortHotels.Travel-Guide-Accommodation) - [Chicago Hotels](https://www.expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Beach Hotel Hotels in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-Beach-Hotel.0-n6132188-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-Boutique-Hotel.0-n6132188-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Family Hotels in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-Family-Hotel.0-n6132188-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-Hotel-With-Pool.0-n6132188-0-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-Hotels-With-Bar.0-n6132188-0-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-LGBT-Friendly-Hotel.0-n6132188-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-Romantic-Hotel.0-n6132188-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Chicago Lawn](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels-Spa-Hotel.0-n6132188-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Chicago Lawn Hotels](https://www.expedia.ca/Chicago-Lawn-Chicago-Hotels.0-n6132188-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Cook County](https://www.expedia.ca/Cook-County-Apart-Hotels.d553248635083916453-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Cook County](https://www.expedia.ca/Cook-County-Bed-And-Breakfast.d553248635083916453-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Motels in Cook County](https://www.expedia.ca/Cook-County-Motels.d553248635083916453-aaMotels.Travel-Guide-Accommodation) - [Resorts in Cook County](https://www.expedia.ca/Cook-County-Resort-Hotels.d553248635083916453-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Damen Station](https://www.expedia.ca/Damen-Station-Townhomes.d6210639-aaTownhomes.Travel-Guide-Accommodation) - [Downtown Chicago Hotels](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Englewood](https://www.expedia.ca/Englewood-Chicago-Hotels-Cheap-Hotels.0-n101911-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Englewood Hotels](https://www.expedia.ca/Englewood-Chicago-Hotels.0-n101911-0.Travel-Guide-Filter-Hotels) - [Apartments in Far Southwest Side](https://www.expedia.ca/Far-Southwest-Side-Apartments.d553248635976475353-aaApartments.Travel-Guide-Accommodation) - [Condo Rentals in Far Southwest Side](https://www.expedia.ca/Far-Southwest-Side-Condos.d553248635976475353-aaCondos.Travel-Guide-Accommodation) - [All Inclusive Resorts and in Gage Park](https://www.expedia.ca/Gage-Park-Chicago-Hotels-All-Inclusive-Hotel.0-n6132375-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Gage Park](https://www.expedia.ca/Gage-Park-Chicago-Hotels-Business-Hotel.0-n6132375-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Gage Park](https://www.expedia.ca/Gage-Park-Chicago-Hotels-Cheap-Hotels.0-n6132375-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Gage Park](https://www.expedia.ca/Gage-Park-Chicago-Hotels-Luxury-Hotel.0-n6132375-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Gage Park Hotels](https://www.expedia.ca/Gage-Park-Chicago-Hotels.0-n6132375-0.Travel-Guide-Filter-Hotels) - [Hotels near Garfield Station](https://www.expedia.ca/Garfield-Station-Hotels.d6210926.Travel-Guide-Hotels) - [Inns in Garfield Station](https://www.expedia.ca/Garfield-Station-Inns.d6210926-aaInns.Travel-Guide-Accommodation) - [Motel 6 Hotels in Glendale](https://www.expedia.ca/Glendale-Chicago-Hotels-Motel-6.0-n6132385-0--bMotel6.Travel-Guide-Filter-Hotels) - [B&B in Halsted Station](https://www.expedia.ca/Halsted-Station-Bed-And-Breakfast.d6211063-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Halsted Station](https://www.expedia.ca/Halsted-Station-Hotels.d6211063.Travel-Guide-Hotels) - [Vacation Homes in Indiana Station](https://www.expedia.ca/Indiana-Station-Private-Vacation-Homes.d6211032-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [B&B in King Drive Station](https://www.expedia.ca/King-Drive-Station-Bed-And-Breakfast.d6211057-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Marquette Park](https://www.expedia.ca/Marquette-Park-Hotels.0-l507385-0.Travel-Guide-Filter-Hotels) - [Boutique Hotels in McKinley Park](https://www.expedia.ca/McKinley-Park-Chicago-Hotels-Boutique-Hotel.0-n6132389-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Four Seasons Hotels in McKinley Park](https://www.expedia.ca/McKinley-Park-Chicago-Hotels-Four-Seasons.0-n6132389-0--bFourSeasons.Travel-Guide-Filter-Hotels) - [Ski Hotels in McKinley Park](https://www.expedia.ca/McKinley-Park-Chicago-Hotels-Ski-Hotel.0-n6132389-0-tSkiHotel.Travel-Guide-Filter-Hotels) - [Mckinley Park Hotels](https://www.expedia.ca/McKinley-Park-Chicago-Hotels.0-n6132389-0.Travel-Guide-Filter-Hotels) - [Hotels near Midway Intl.](https://www.expedia.ca/Midway-Intl-Airport-Hotels.0-aMDW-0.Travel-Guide-Filter-Hotels) - [B&B in Midway Station](https://www.expedia.ca/Midway-Station-Bed-And-Breakfast.d6211025-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Midway Station](https://www.expedia.ca/Midway-Station-Hotels.d6211025.Travel-Guide-Hotels) - [Motels in Midway Station](https://www.expedia.ca/Midway-Station-Motels.d6211025-aaMotels.Travel-Guide-Accommodation) - [Beach Hotel Hotels in New City](https://www.expedia.ca/New-City-Chicago-Hotels-Beach-Hotel.0-n6132388-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in New City](https://www.expedia.ca/New-City-Chicago-Hotels-Boutique-Hotel.0-n6132388-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in New City](https://www.expedia.ca/New-City-Chicago-Hotels-Hotel-With-Pool.0-n6132388-0-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in New City](https://www.expedia.ca/New-City-Chicago-Hotels-LGBT-Friendly-Hotel.0-n6132388-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in New City](https://www.expedia.ca/New-City-Chicago-Hotels-Luxury-Hotel.0-n6132388-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in New City](https://www.expedia.ca/New-City-Chicago-Hotels-Pet-Friendly-Hotel.0-n6132388-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [New City Hotels](https://www.expedia.ca/New-City-Chicago-Hotels.0-n6132388-0.Travel-Guide-Filter-Hotels) - [Hotels near Pulaski Station](https://www.expedia.ca/Pulaski-Station-Hotels.d6211019.Travel-Guide-Hotels) - [Condo Rentals in South Side](https://www.expedia.ca/South-Side-Condos.d553248635074842823-aaCondos.Travel-Guide-Accommodation) - [Motels in South Side](https://www.expedia.ca/South-Side-Motels.d553248635074842823-aaMotels.Travel-Guide-Accommodation) - [Resorts in South Side](https://www.expedia.ca/South-Side-Resort-Hotels.d553248635074842823-aaResortHotels.Travel-Guide-Accommodation) - [Cheap Hotels in West Englewood](https://www.expedia.ca/West-Englewood-Chicago-Hotels-Cheap-Hotels.0-n6132412-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [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)