Title: Book the Best South Side LUXURY Hotels - Upscale Hotels in South Side, IL | Expedia.ca

[South Side Travel Guide](https://expedia.ca/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.ca/South-Side.d553248635074842823.Destination-Travel-Guides)

![I thought Wood Ducks were the most amazingly colorful and photogenic ducks until I spotted this incredible bird on the lakefront. What a handsome beautiful duck. ](https://images.trvl-media.com/place/829/3b8962fc-94e7-486b-84ab-96e09a77459b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Richard Remington

# Find luxury hotels in South Side, IL

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## Check availability on South Side Luxury Hotels

Tonight

[Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-10&endDate=2025-12-11&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

Tomorrow

[Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-11&endDate=2025-12-12&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

This weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-12&endDate=2025-12-14&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-19&endDate=2025-12-21&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

## Our top choices for South Side luxury hotels

![View from room](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f98af4f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f1fd01e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/8f681739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 2 Queen Beds](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/b456698d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sophy Hyde Park

[](https://www.expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information)

Hyde Park

9.6/10

Exceptional

(1001)

"Great staff, location and ambience."

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

Jaison

CA $236

CA $315 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information)

![American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/ab309a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/a073ef3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/64fc97f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/69e6751f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Godfrey Hotel Chicago

[](https://www.expedia.ca/Chicago-Hotels-The-Godfrey-Hotel-Chicago.h7063210.Hotel-Information)

Downtown Chicago

8.6/10

Excellent

(1919)

"Good value, great cleaning staff "

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

farzana

CA $132

CA $187 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Chicago-Hotels-The-Godfrey-Hotel-Chicago.h7063210.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/6ccd2813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges, rooftop bar, cocktail bar](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/be0e472a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LondonHouse Chicago, Curio Collection by Hilton

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

Downtown Chicago

9.4/10

Exceptional

(3419)

"Great Hotel!"

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

Siranush

CA $181

CA $212 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![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)

![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2695x3y3-e619dd92.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)

### Hyatt Regency Chicago

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

Downtown Chicago

9.4/10

Exceptional

(3398)

"I always love staying at this place when I visit"

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

William

CA $188

CA $262 total

includes taxes & fees

Dec 22 - Dec 23

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

![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)

![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/943262bb.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)

![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/c042bdff.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

(1508)

"Everything was really wonderful.. would stay again for sure!! "

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

Alexa

CA $140

CA $164 total

includes taxes & fees

Dec 15 - Dec 16

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

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/4c0ebbe4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/e436fe11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/311c65a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV, Netflix, pay movies, streaming services](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/edeb1954.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sheraton Grand Chicago Riverwalk

[](https://www.expedia.ca/Chicago-Hotels-Sheraton-Grand-Chicago.h12167.Hotel-Information)

Downtown Chicago

8.4/10

Very good

(1577)

"Rooms were very nice and staff was great"

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

Nancy

CA $206

CA $284 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Chicago-Hotels-Sheraton-Grand-Chicago.h12167.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Serves breakfast, lunch, and dinner](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/b0f5bd1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/04b62050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/05f95ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Silversmith Hotel Chicago Downtown

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

Downtown Chicago

9.2/10

Wonderful

(2110)

"Great hotel. Very affordable for such a perfect location."

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

Nicholas

CA $112

CA $174 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e.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)

![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b1113923.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

(2180)

"Nice Hotel"

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

Alan

CA $124

CA $145 total

includes taxes & fees

Dec 21 - Dec 22

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

![View from room](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/4d5fc313.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

[](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(3350)

"I loved the location."

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

Laura

CA $195

CA $229 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information)

![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/7e178380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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/b376d4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/2e9bef56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairmont Chicago at Millennium Park

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

Downtown Chicago

8.6/10

Excellent

(2012)

"Great accommodation!"

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

James

CA $236

CA $317 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Chicago-Hotels-Fairmont-Chicago-At-Millennium-Park.h15937.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=2025-12-24&endDate=2025-12-25&regionId=553248635074842823&adults=2&sort=LUXURY&star=50&openPlayBack=true)

## Top South Side Hotel Reviews

![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg)

### Chinatown Hotel Chicago

10/10 Excellent

"y"

[](https://expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information)

![Carlton Inn Midway](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg)

### Carlton Inn Midway

10/10 Excellent

"Staff is great, clean rooms "

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

![Hyatt Place Chicago-South/University Medical Center](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg)

### Hyatt Place Chicago-South/University Medical Center

10/10 Excellent

"Kim, at the front desk,was welcoming and helpful. She was sooooo kind and considerate!"

[](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information)

![Chicago Marriott Midway](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg)

### Chicago Marriott Midway

10/10 Excellent

"Very convenient and clean and friendly! "

[](https://expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information)

![Best Western Inn & Suites - Midway Airport](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/92ee0c20_y.jpg)

### Best Western Inn & Suites - Midway Airport

10/10 Excellent

"Hotel and room was very clean and the desk clerk was courteous "

[](https://expedia.ca/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information)

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