Title: Southwest Side Villas from CA $119 | 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)

![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

# Search Southwest Side Villa Rentals from CA $119

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## Check prices for these dates

In two weeks

[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)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

No exact matches found, but these alternatives could be just right

## Recommended hotels in Southwest Side

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/w3835h2161x6y0-831944db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/5cebb64b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/5bc8bb1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/450ed27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Chicago – Midway Airport S by IHG

[](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information)

West Lawn

8.4/10

Very good

(1000)

"Great stay"

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

Maria

CA $140

CA $178 total

includes taxes & fees

Dec 25 - Dec 26

[](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/2b5be5e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1278h1921x2y2-bce03282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1350h899x0y1-09740a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1350h899x0y1-43718ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

[](https://www.expedia.ca/Chicago-Hotels-Sunflower-Apt-12-Min-From-Downtown-CHI.h91086437.Hotel-Information)

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 $120

CA $327 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Chicago-Hotels-Sunflower-Apt-12-Min-From-Downtown-CHI.h91086437.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/b7fc4c02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1350h899x0y1-b9b7a110.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)

![Interior](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1349h899x1y1-922f1c40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

[](https://www.expedia.ca/Chicago-Hotels-W-Pershing-Large-Chicago-Apt-3-Bed-12-Min-Downtown-Arcade.h96479287.Hotel-Information)

Brighton Park

9.2/10

Wonderful

(7)

"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "

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

Jessica H.

CA $153

CA $421 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Chicago-Hotels-W-Pershing-Large-Chicago-Apt-3-Bed-12-Min-Downtown-Arcade.h96479287.Hotel-Information)

![Airport shuttle](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/7cf036af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Traditional Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/efb1181a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/26ad2ef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Carlton Inn Midway

[](https://www.expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information)

Archer Heights

6.4/10

(1001)

"The room was clean and satisfied our needs. Was handy using their shuttle to Midway Airport."

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

Charles

CA $136

CA $160 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/70677983.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/a2a4ef31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/6c3662e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/953521af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Skylark Motel

[](https://www.expedia.ca/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information)

Garfield Ridge

4.6/10

(119)

"Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal."

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

Stephen

CA $113

CA $133 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/b6619f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/dfae7ccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 Queen Bed, Jetted Tub](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/2a2055fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free toiletries, towels](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/62a8a4cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rainbow Motel

[](https://www.expedia.ca/Chicago-Hotels-Rainbow-Motel.h115345673.Hotel-Information)

Garfield Ridge

5.8/10

(18)

"It was a good stay the rooms are small tho but if you are going to have fun and just have somewhere to sleep then it’s perfect for a couple people "

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

Conner

CA $133

CA $170 total

includes taxes & fees

Dec 25 - Dec 26

[](https://www.expedia.ca/Chicago-Hotels-Rainbow-Motel.h115345673.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/56c2d84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/693d9c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Banquet hall](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/2ad62276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/352e3b39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aloft Chicago Mag Mile

[](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information)

Downtown Chicago

8.6/10

Excellent

(2976)

"Great place to stay"

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

Elisha

CA $118

CA $139 total

includes taxes & fees

Jan 22 - Jan 23, 2026

[](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/7153c023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/444bc42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, breakfast, lunch, dinner served; Latin American cuisine](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/cadeb422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

[](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(2284)

"Great staff and restaurants!!"

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

Abigale

CA $118

CA $186 total

includes taxes & fees

Jan 20 - Jan 21, 2026

[](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/5bec7925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e50ef89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/d37889fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/dfb99e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River Hotel

[](https://www.expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(4861)

"Great location, comfortable room, and nice staff."

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

Claudia

CA $107

CA $125 total

includes taxes & fees

Jan 21 - Jan 22, 2026

[](https://www.expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/461957e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/3a5d3e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/6234383e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/b90174ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Centric Chicago Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(1059)

"Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food."

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

Hannah

CA $135

CA $199 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b5bf3aa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/bbeef356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/f2c5642d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Chicago

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

Downtown Chicago

8.4/10

Very good

(2413)

"The room was clean and the staff was outstanding. "

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

Albert

CA $157

CA $224 total

includes taxes & fees

Dec 29 - Dec 30

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

![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/w3995h2667x0y0-afbbbc14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6d9bcb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Wade

[](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information)

Downtown Chicago

8.4/10

Very good

(1535)

"Great staff and great location. "

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

Joe

CA $139

CA $163 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/34f4da65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/a9fdeea6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/6f539c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Warwick Allerton - Chicago

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

Downtown Chicago

8.4/10

Very good

(3018)

"Enjoyed this hotel stay. "

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

Kimberly

CA $88

CA $144 total

includes taxes & fees

Dec 28 - Dec 29

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

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/8e39b688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/a08c52fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/d7ae47e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b131add8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DoubleTree by Hilton Chicago - Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(2206)

"Very friendly staff, clean rooms, the location is amazing and near of everything "

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

Sarwat

CA $123

CA $144 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/69000000/68110000/68102900/68102882/w5996h4000x0y0-15560d81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/69000000/68110000/68102900/68102882/b4eabe81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, laptop workspace, bed sheets](https://images.trvl-media.com/lodging/69000000/68110000/68102900/68102882/3198ccde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/69000000/68110000/68102900/68102882/8ff08db7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Chicago Central Loop

[](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Central-Loop.h68102882.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(1269)

"Great location!"

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

WINDALEE

CA $127

CA $149 total

includes taxes & fees

Jan 10 - Jan 11, 2026

[](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Central-Loop.h68102882.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/cc779b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges, rooftop bar](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/33cb1dae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges, rooftop bar](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/w2990h1178x0y0-a3dcd2ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Riu Plaza Chicago

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(3031)

"Excellent stay great location and great rooms"

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

Joseph

CA $137

CA $200 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/fb110cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3840h2559x0y3-c577bf94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3840h1497x0y3-3b277bb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2560x3y0-ce2754d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Regency Chicago

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

Downtown Chicago

9.4/10

Exceptional

(3411)

"The Hotel was amazing great location "

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

Donnisha

CA $191

CA $265 total

includes taxes & fees

Jan 5 - Jan 6, 2026

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

![Exterior detail](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e43f096f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Suite, City View | City view](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/3e0e58e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/086ff612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Congress Plaza Hotel

[](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

Downtown Chicago

8.0/10

Very good

(9692)

"Wonderful stay!"

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

Zach

CA $111

CA $130 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/4306fa2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/d2c9858e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/b3bac7c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/d4307099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Club Quarters Hotel Wacker at Michigan, Chicago

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

Downtown Chicago

8.8/10

Excellent

(2007)

"Great stay"

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

Kramer

CA $101

CA $119 total

includes taxes & fees

Jan 18 - Jan 19, 2026

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

![Exterior](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/2435ca6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/0ea4e737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/ec33d4f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Embassy Suites by Hilton Chicago Downtown Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information)

Downtown Chicago

8.2/10

Very good

(2758)

"Excellent place to stay "

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

Teniesha

CA $108

CA $167 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.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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Cottages

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Condos

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Private vacation homes

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Residences

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## Top Southwest Side Hotel Reviews

![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg)

### LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent

"Excellent staff. Thanks Shams for your excellent customer service and making my daughter's 21st birthday special."

[](https://expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information)

![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg)

### River Hotel

10/10 Excellent

"It's great "

[](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg)

### The Royal Sonesta Chicago Downtown

10/10 Excellent

"The lady who checked us in (the countess) was very friendly and welcoming. Even though she was the only person working the front desk, she did not get frazzled or curt. She was great! Room was beautiful and had an amazing view!"

[](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.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

"Staff was friendly and helpful. Our room was comfortable and had a great city view."

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

![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg)

### Swissotel - Chicago

10/10 Excellent

"Everyone was nice and helpful. Room was clean and the hotel location is great"

[](https://expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information)

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent

"The room was amazing, views were amazing, staff is very friendly and helpful, I’m definitely coming back here for sure ."

[](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg)

### Palmer House a Hilton Hotel

10/10 Excellent

"Staff was so amazing nice and helpfuk"

[](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information)

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

### Hilton Chicago

10/10 Excellent

"Amazing experience! The rooms were spotless, comfortable, and thoughtfully maintained. All hotel amenities were clean, well-organized, and ready to use. The breakfast was excellent, with a great variety of options to choose from. What truly made this stay extraordinary was the outstanding service. Brad, Vicente, Cruz, Eric, Ruby, and the entire team went above and beyond to ensure a memorable experience. Their professionalism, kindness, and attention to detail were exceptional. Without a doubt, this was a unique and unforgettable stay — truly a hotel that exceeds five-star expectations. ❤️"

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

![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg)

### Silversmith Hotel Chicago Downtown

10/10 Excellent

"The staff went above and beyond for us. We got in real late after midnight and they were extremely accommodating. Since we were flying all day on my fiancé birthday i had asked for them to leave a little happy birthday note in the room when we arrived. They left a birtday card and a box of whoppers for her. That was amazing. The whole staff was top notch. "

[](https://expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information)

## Find out more about Southwest Side

## Southwest Side Villas information

| Number of reviews | 43,524   |
| ----------------- | -------- |
| Accommodation     | 2 Villas |
| Lowest Price      | CA $119  |
| Highest Price     | CA $421  |

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- [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)
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- [Book Villas in Southwest Side on Expedia.com ](https://www.expedia.com/Southwest-Side-Villas.d553248635976475403-aaVillas.Travel-Guide-Accommodation)