Title: 4 Stars Hotels in Southwest Side, Chicago from CA $148 - Find Cheap Southwest Side Hotels With 4 Stars | 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)

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# 4 Stars Hotels in Southwest Side, Chicago from CA $148

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## Check availability on Southwest Side 4 Star Hotels

Tonight

[Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-15&endDate=2025-10-16&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-16&endDate=2025-10-17&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Southwest Side 4 Star Hotels

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/0a522c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/896a6d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/9b9a583c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

8.6/10

Excellent

(5095)

"Great place, good breakfast and the location "

CA $202

CA $237 total

includes taxes & fees

Nov 9 - Nov 10

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

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/e7e820fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/3fb360e9.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/1000000/10000/8100/8058/6402f922.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Chicago O'Hare Airport

O'Hare

8.2/10

Very good

(2141)

"Location is very convenient for travellers "

CA $263

CA $308 total

includes taxes & fees

Nov 7 - Nov 8

[](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.Hotel-Information)

![Daily full breakfast (USD 27.76 per person)](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/46cc150a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/57e178a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/d075b709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 Double Beds Premier Tower](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/aa7843d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Regency O'Hare Chicago

O'Hare

8.8/10

Excellent

(2069)

"Had a very nice stay."

CA $202

CA $230 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-OHare-Chicago.h5403.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/ca00b143.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/67428c96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/d91ad5fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/6c4a5051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Chicago Hotel Collection - Magnificent Mile

Downtown Chicago

7.4/10

Good

(1100)

"Great location, spacious rooms"

CA $191

CA $224 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/1792d463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed, City View | View from room](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/c06f4b61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily buffet breakfast (USD 20.00 per person)](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/8967eebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### citizenM Chicago Downtown

Downtown Chicago

9.2/10

Wonderful

(3951)

"Great place to stay. "

CA $184

CA $216 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information)

![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)

![Standard Room](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/22cb8b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/ccacdd84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/023ff9a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Warwick Allerton - Chicago

Downtown Chicago

8.4/10

Very good

(2926)

"The lodging was super nice."

CA $129

CA $193 total

includes taxes & fees

Nov 12 - Nov 13

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

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/89e1318d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/42397db2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/5785af38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

9.0/10

Wonderful

(2497)

"Great stay "

CA $289

CA $384 total

includes taxes & fees

Nov 9 - Nov 10

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

![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Room, 2 Queen Beds, Lake View](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2561x3y0-ec3252d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/4df3bcb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Regency Chicago

Downtown Chicago

9.4/10

Exceptional

(3386)

"All around great stay"

CA $326

CA $424 total

includes taxes & fees

Oct 30 - Oct 31

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

![Reception](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/511c43ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Single Beds](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/6d4883c6.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)

### River Hotel

Downtown Chicago

8.8/10

Excellent

(4746)

"Staff friendly and helpful..and accommodations just right..great location! "

CA $143

CA $168 total

includes taxes & fees

Nov 11 - Nov 12

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

![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/ec9ee4a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/dffcca17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/16c54b79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

9.0/10

Wonderful

(2137)

"We had an amazing stay for a weekend getaway. "

CA $167

CA $241 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information)

![City view](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/64dd2430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/d8be0ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 restaurants, breakfast, lunch, dinner served; Asian cuisine](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/947219c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/df55aaa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Hyatt Regency McCormick Place Chicago

Near South Side

9.0/10

Wonderful

(1012)

"Excellent stay!"

CA $336

CA $427 total

includes taxes & fees

Nov 8 - Nov 9

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-McCormick-Place.h84736.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/6dfbfa42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/12c82a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/1272603a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/bf403e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### L7 Chicago by LOTTE

Downtown Chicago

9.6/10

Exceptional

(3085)

"Great hotels "

CA $278

CA $327 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.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/bbeef356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b812d0f0.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

Downtown Chicago

8.4/10

Very good

(2261)

"We loved this hotel it was beautiful and convenient . "

CA $258

CA $344 total

includes taxes & fees

Oct 30 - Oct 31

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

![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/9097f753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/279c3768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![City view from property](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/2b1c0fd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Felix River North/Magnificent Mile

Downtown Chicago

8.2/10

Very good

(2278)

"Great stay and great location "

CA $114

CA $177 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information)

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

![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/e47956bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/943262bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Wade

Downtown Chicago

8.4/10

Very good

(1369)

"Great place to stay"

CA $190

CA $223 total

includes taxes & fees

Nov 2 - Nov 3

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

![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/19b0236f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Queen Bed, Kitchenette](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/a9bc446d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/aaae0504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Queen Bed, Kitchenette](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/01e59f66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

8.8/10

Excellent

(3351)

"Great location, nice rooms"

CA $153

CA $179 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h565746.Hotel-Information)

![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/aaad0ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/01c93cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/8318473d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Palmer House a Hilton Hotel

Downtown Chicago

8.4/10

Very good

(2017)

"Great place to stay."

CA $253

CA $332 total

includes taxes & fees

Oct 30 - Oct 31

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

![Front of property](https://images.trvl-media.com/lodging/1000000/10000/9600/9529/8f0b88a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pillowtop beds, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/9600/9529/06e4d0df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9529/1ed17318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/9600/9529/5ac21fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DoubleTree by Hilton Lisle Naperville

Naperville

7.8/10

Good

(1179)

"Great stay "

CA $134

CA $148 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Lisle-Naperville.h9529.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6600/6545/8dd24dc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/6600/6545/b44ba019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/6600/6545/585e65d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/6600/6545/48bc466d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

Wood Dale

8.2/10

Very good

(1033)

"Very cool place "

CA $137

CA $152 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Wood-Dale-Elk-Grove.h6545.Hotel-Information)

![Executive lounge](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Steam room, body treatments, facials, 2 treatment rooms, massages](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/037db98f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Steam room, body treatments, facials, 2 treatment rooms, massages](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/b376d4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/84fcc5bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairmont Chicago at Millennium Park

Downtown Chicago

8.6/10

Excellent

(1996)

"Perfect location, very clean, super comfy bed + pillows! Would stay there again! "

CA $357

CA $460 total

includes taxes & fees

Oct 23 - Oct 24

[](https://www.expedia.ca/Chicago-Hotels-Fairmont-Chicago-At-Millennium-Park.h15937.Hotel-Information)

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## Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Southwest Side.

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Trump International Hotel & Tower Chicago

401 N Wabash Ave, Chicago, IL

CA $606

CA $711 total

Nov 2 - Nov 3

includes taxes & fees

9.4/10 Exceptional! (1,750 reviews)

[](https://expedia.ca/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information)

![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Langham, Chicago

330 North Wabash Avenue, Chicago, IL

CA $764

CA $896 total

Nov 9 - Nov 10

includes taxes & fees

9.6/10 Exceptional! (1,007 reviews)

[](https://expedia.ca/Chicago-Hotels-The-Langham.h6309326.Hotel-Information)

![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Peninsula Chicago

108 East Superior Street, Chicago, IL

CA $878

CA $1,030 total

Nov 9 - Nov 10

includes taxes & fees

9.6/10 Exceptional! (1,003 reviews)

[](https://expedia.ca/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information)

Still don't see what you're looking for?

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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.

## Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and Union Stock Yard Gate as you discover things to see and do in Southwest Side.

[See all hotels in Southwest Side](https://www.expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30&adults=2&regionId=553248635976475403)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495661-chicago-il-mdw-midway-intl.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high)

Photo by by Midway Intl Airport

## Top Southwest Side Hotel Reviews

![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

"We did the corner suite and it was amazing waking up with the sunrise over the lake. "

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

![DoubleTree by Hilton Chicago - Magnificent Mile](//images.trvl-media.com/lodging/1000000/30000/21200/21152/b1113923_y.jpg)

### DoubleTree by Hilton Chicago - Magnificent Mile

10/10 Excellent

"This was perfect for Chicago Marathon. Good proximity to start and finish (about a mile) and was excellent location for spectating. "

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

"Breakfast was great! "

[](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information)

![citizenM Chicago Downtown](//images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd_y.jpg)

### citizenM Chicago Downtown

10/10 Excellent

"Great place with lots to do as it is right I. The downtown, so Riverwalk one at and grant park the other. No outlets by beds so bring long cords "

[](https://expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.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

"This was the best hotel I ever stayed at! I did not want to leave. It was very clean and the cleaning staff was attentive and thorough. The staff at the desk were friendly and knowledgeable, and never acted disgruntled or impatient. The bellhops were excellent and trustworthy and anticipated our needs. The hotel was just beautiful and clean in the lobby with boutique atmosphere and art. The room was spacious with comfortable bed and furnishings. The coffee was excellent and the bathroom felt luxurious. We just loved everything! The restaurant food was great quality and not overpriced. And, our location downtown couldn’t be better, near Riverwalk and Michigan Avenue. We thoroughly enjoyed our stay. Thank you, Sonesta!"

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

![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg)

### Freehand Chicago

10/10 Excellent

"All the staff had great energy and were very helpful. Nice bar/lounge area and cozy space. I had a private room and though it wasn’t huge, it was exactly what we needed for our staycation."

[](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information)

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

### Warwick Allerton - Chicago

10/10 Excellent

"Everything was great. It was awesome being back in Chicago again. "

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

![Hotel Riu Plaza Chicago](//images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg)

### Hotel Riu Plaza Chicago

10/10 Excellent

"Great Location!"

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

"The onsite parking is worth the money compared to other lots. Walk where you can. The Embassy is in the perfect location for a lot of attractions."

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

## Find out more about Southwest Side

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Southwest Side are calling your name. Known for providing first-rate service in amazing locations, each of the Southwest Side 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Southwest Side. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Southwest Side, Chicago, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Southwest Side hotels with 4 Stars provide everything you need to unwind in style.

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-   [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 Toronto (YTZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-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 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 4 Star Hotels in Southwest Side on Expedia.com](https://www.expedia.com/4Star-Southwest-Side-Hotels.s40-0-d553248635976475403.Travel-Guide-Filter-Hotels)