Title: Southwest Side Vacation Rentals from CA $118: Short-Term Rentals for 2026 | 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)[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)

![Chicago, IL showing interior views, heritage elements and an airport](https://images.trvl-media.com/place/5719117/ef1b962b-07e6-469b-abf5-73ab99ceb6ee.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by by Midway Intl Airport

# Southwest Side Vacation Rentals

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## Check prices for these dates

Tonight

[Dec 25 - Dec 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-25&endDate=2025-12-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-26&endDate=2025-12-27&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Southwest Side vacation rentals

![Front of property](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/44167e80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/w1320h783x0y1-af1e2329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Duplex, City View | Shared kitchen](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/14e4f60e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/27e8c783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago luxury home suites

[](https://www.expedia.ca/Chicago-Hotels-Chicago-Luxury-Home-Suites.h121424489.Hotel-Information)

Downtown Chicago

8.4/10

Very good

(5)

"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Alex

CA $180

CA $212 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Chicago-Hotels-Chicago-Luxury-Home-Suites.h121424489.Hotel-Information)

![Business centre](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/825d44e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cafe](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/715d8399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/f7e5c565_edited_04eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/860305fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa River North Chicago

[](https://www.expedia.ca/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(182)

"Awesome stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sally

[](https://www.expedia.ca/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/cb208a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/a7a120b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/9bdb478c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Level Chicago – Old Town

[](https://www.expedia.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(405)

"Great location, clean room and friendly staff!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott

CA $200

CA $265 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.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)

![City Apartment, City View | Living area](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/7fc927d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/c94fe51a.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)

### ENVITAE Hotel 4 Bedroom Luxury Apartments

[](https://www.expedia.ca/Chicago-Hotels-4BR-Corporate-Suite-Central-And-Modern.h118632066.Hotel-Information)

Near North Side

10/10

Exceptional

(8)

"We loved at our stay at this property. It was one of the best stays we have had on vacation."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Javeria

CA $1,144

CA $1,631 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Chicago-Hotels-4BR-Corporate-Suite-Central-And-Modern.h118632066.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/a9b3121a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/eacd6d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ccaab668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio, 1 Queen Bed (Studio Apartment) | Private kitchen](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/1bf06d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sentral Michigan Avenue

[](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(1021)

"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Deidre

CA $162

CA $230 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

![Studio | Exterior](https://images.trvl-media.com/lodging/95000000/94960000/94953700/94953678/6530bd2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953700/94953678/320e9643.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Private kitchen](https://images.trvl-media.com/lodging/95000000/94960000/94953700/94953678/5732d3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Living area](https://images.trvl-media.com/lodging/95000000/94960000/94953700/94953678/f2bcf415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin 105 by 747 Lofts

[](https://www.expedia.ca/Chicago-Hotels-Cabin-105-By-747-Lofts.h94953678.Hotel-Information)

West Town

10/10

Exceptional

(1)

CA $81

CA $183 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Chicago-Hotels-Cabin-105-By-747-Lofts.h94953678.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/06060406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/c25a1316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3e6dada5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/2626f596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wrigleyville Suites

[](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information)

Lakeview

9.6/10

Exceptional

(26)

"Excellent location and very clean! Would stay again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jacob

CA $187

CA $220 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information)

![Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/acb706d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/a77496eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio Suite, 1 Double Bed, Kitchen (Washer/Dryer)](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/fe592b2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom, Kitchen (Washer/Dryer) | Private kitchen](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/38d26f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Gem Museum Suites

[](https://www.expedia.ca/Chicago-Hotels-The-Gem-Museum-Suites.h103465448.Hotel-Information)

Downtown Evanston

9.4/10

Exceptional

(99)

"Great stay. The studio is small but has everything necessary."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Julia

CA $241

CA $276 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Chicago-Hotels-The-Gem-Museum-Suites.h103465448.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)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/fd6bd1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/733d465a.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)

### The Oak Park Loft

[](https://www.expedia.ca/Chicago-Hotels-The-Oak-Park-Loft.h107622605.Hotel-Information)

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)

![Comfort Double Room](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/22fe051f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Studio](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/d6f1cd2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, blackout drapes, free WiFi](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/7a3c031a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/81879fe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn Chicago Southland I-80 & I-294 Near Casino

[](https://www.expedia.ca/Chicago-Hotels-Comfort-Inn-Chicago-Wind-Creek-Casino.h112306435.Hotel-Information)

Harvey

4.0/10

(68)

"Good "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Abel

CA $104

CA $118 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Chicago-Hotels-Comfort-Inn-Chicago-Wind-Creek-Casino.h112306435.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121340000/121330200/121330192/7db98038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121340000/121330200/121330192/ee4be839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121340000/121330200/121330192/df9330f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121340000/121330200/121330192/f9a49026.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Classic Forest Park Foursquare < 1 Mi to Blue Line

[](https://www.expedia.ca/Chicago-Hotels-Classic-Forest-Park-Foursquare-1-Mi-To-Blue-Line.h121330192.Hotel-Information)

Forest Park

CA $216

CA $564 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Chicago-Hotels-Classic-Forest-Park-Foursquare-1-Mi-To-Blue-Line.h121330192.Hotel-Information)

![Studio | Exterior](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/c46e5d6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Private kitchen](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/aea930d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Living area](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/f9632e6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Living area](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/9718e304.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago Third Floor Studio by 747 Lofts

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-Local-Hot-Spots-Or-Public-Transit-Prime-Location-In-The-Heart-Of-The-Windy-City-747-Lofts-Cabin-301-Hotel-Room.h88902334.Hotel-Information)

West Town

9.8/10

Exceptional

(6)

"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer

CA $87

CA $306 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-Local-Hot-Spots-Or-Public-Transit-Prime-Location-In-The-Heart-Of-The-Windy-City-747-Lofts-Cabin-301-Hotel-Room.h88902334.Hotel-Information)

![Studio | Exterior](https://images.trvl-media.com/lodging/89000000/88870000/88870000/88869908/16bd767b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Private kitchen](https://images.trvl-media.com/lodging/89000000/88870000/88870000/88869908/2845922d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Living area](https://images.trvl-media.com/lodging/89000000/88870000/88870000/88869908/87fc1015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | View from property](https://images.trvl-media.com/lodging/89000000/88870000/88870000/88869908/2a68ef52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River West, Second Floor Chicago by 747 Lofts

[](https://www.expedia.ca/Chicago-Hotels-You-Cant-Beat-This-Location-For-Exploring-The-Great-Windy-City-747-Lofts-Cabin-201-Hotel-Room.h88869908.Hotel-Information)

West Town

9.6/10

Exceptional

(4)

"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

CA $88

CA $308 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Chicago-Hotels-You-Cant-Beat-This-Location-For-Exploring-The-Great-Windy-City-747-Lofts-Cabin-201-Hotel-Room.h88869908.Hotel-Information)

![Studio | Private kitchen](https://images.trvl-media.com/lodging/89000000/88880000/88878700/88878619/1dcce3d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio](https://images.trvl-media.com/lodging/89000000/88880000/88878700/88878619/c9be2ffd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Private kitchen](https://images.trvl-media.com/lodging/89000000/88880000/88878700/88878619/f4776659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Living area](https://images.trvl-media.com/lodging/89000000/88880000/88878700/88878619/811b307f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago Second Floor Studio by 747 Lofts

[](https://www.expedia.ca/Chicago-Hotels-Full-Kitchen.h88878619.Hotel-Information)

West Town

8.8/10

Excellent

(13)

"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Barbara

CA $89

CA $194 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Chicago-Hotels-Full-Kitchen.h88878619.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.

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## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Condos

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## Top Southwest Side Hotel Reviews

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg)

### Eurostars Magnificent Mile

10/10 Excellent

"10 out of 10 will definitely be back! "

[](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg)

### Club Quarters Hotel Wacker at Michigan, Chicago

10/10 Excellent

"Clean room...friendly staff"

[](https://expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information)

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg)

### Hilton Chicago

10/10 Excellent

"What a great stay!!"

[](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information)

![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg)

### Warwick Allerton - Chicago

10/10 Excellent

"Clean room"

[](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"I prefer Embassy Suite over any hotel. ES does not fail in quality, comfort, cleanliness. We enjoyed Chicago very much. Embassy Suite was in walking distance. Staff were very friendly. "

[](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information)

![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg)

### Hyatt Regency Chicago

10/10 Excellent

"."

[](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information)

![InterContinental Chicago Magnificent Mile by IHG](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg)

### InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Nice place and staff!!"

[](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information)

![Crowne Plaza Chicago West Loop by IHG](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg)

### Crowne Plaza Chicago West Loop by IHG

10/10 Excellent

"I loved the balcony the most. 10/10."

[](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information)

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Staff was incredibly welcoming upon arrival and was fantastic throughout the stay! Perfect location for walking as well as catching the train, can’t recommend enough"

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

## Find out more about Southwest Side

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Southwest Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

## Explore a world of travel with Expedia

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- [Apartments in Southwest Side ](https://expedia.ca/Southwest-Side-Apartments.d553248635976475403-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in Southwest Side ](https://expedia.ca/Southwest-Side-Private-Vacation-Homes.d553248635976475403-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Southwest Side ](https://expedia.ca/Southwest-Side-Condos.d553248635976475403-aaCondos.Travel-Guide-Accommodation)
- [Motels in Southwest Side ](https://expedia.ca/Southwest-Side-Motels.d553248635976475403-aaMotels.Travel-Guide-Accommodation)
- [Aparthotels in Southwest Side ](https://expedia.ca/Southwest-Side-Apart-Hotels.d553248635976475403-aaApartHotels.Travel-Guide-Accommodation)
- [Cottages in Southwest Side ](https://expedia.ca/Southwest-Side-Cottages.d553248635976475403-aaCottages.Travel-Guide-Accommodation)
- [B&B in Southwest Side ](https://expedia.ca/Southwest-Side-Bed-And-Breakfast.d553248635976475403-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Southwest Side ](https://expedia.ca/Southwest-Side-Guest-Houses.d553248635976475403-aaGuestHouses.Travel-Guide-Accommodation)
- [Hostels in Southwest Side ](https://expedia.ca/Southwest-Side-Hostels.d553248635976475403-aaHostels.Travel-Guide-Accommodation)
- [Resorts in Southwest Side ](https://expedia.ca/Southwest-Side-Resort-Hotels.d553248635976475403-aaResortHotels.Travel-Guide-Accommodation)
- [Villas in Southwest Side ](https://expedia.ca/Southwest-Side-Villas.d553248635976475403-aaVillas.Travel-Guide-Accommodation)
- [Farmstay in Southwest Side ](https://expedia.ca/Southwest-Side-Agritourism.d553248635976475403-aaAgritourism.Travel-Guide-Accommodation)

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