A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

Luxury Hotels & Resorts in South Side from AU$172

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Check availability on South Side Luxury Hotels

Tonight
2 Sept - 3 Sept
Tomorrow
3 Sept - 4 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

Our top choices for South Side luxury hotels

A modern hotel room with large windows, a sofa, chairs, a dining table, and a coffee table.
A multi-story hotel with a modern design, featuring a prominent entrance with a marquee and outdoor seating area.
An outdoor seating area with sofas, chairs, and tables, surrounded by trees and string lights.
A bar area with a marble countertop, multiple shelves of bottles, and a large TV screen. There are several bar stools and a round table with a vase of flowers.

1. Sophy Hyde Park

Sophy Hyde Park
Hyde Park
  • Luxury meets cultural charm in Hyde Park Chicago, where plush bedding and upscale dining create an elegant retreat near lakefront parks.
AU$442
includes taxes & fees
7 Sept - 8 Sept
Sophy Hyde Park
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.
A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.
A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.

2. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
AU$352
includes taxes & fees
8 Sept - 9 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
A spacious lobby with a patterned carpet, comfortable seating, a fireplace, and large windows.
A large, historic building with a central courtyard surrounded by trees.
A cityscape with modern high-rise buildings, a train station, and a body of water in the background.
A rooftop lounge with outdoor seating and a view of the city skyline.

3. Hilton Chicago

Hilton Chicago
Downtown Chicago
AU$322
includes taxes & fees
9 Sept - 10 Sept
Hilton Chicago
A spacious lobby with a central coffee table, sofas, and a large mirror.
A spacious lobby with high ceilings, large arched windows, and a grand staircase.
A spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.
A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.

4. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
AU$202
includes taxes & fees
8 Sept - 9 Sept
The Chicago Hotel Collection Ambassador Gold Coast
A modern kitchen with a marble island, fruit bowls, and a city view.
A modern lounge area with a central bar, seating arrangements, and a decorative chandelier.
A Fairmont hotel with a prominent entrance, large windows, and a sculpture on the facade.
A modern hotel room with a city view, a seating area with two sofas and a coffee table, and a dining area with a table and chairs.

5. Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
Downtown Chicago
AU$406
includes taxes & fees
8 Sept - 9 Sept
Fairmont Chicago at Millennium Park
A spacious bar area with high ceilings and large windows, offering views of a cityscape.
A multi-level hotel lobby with a glass elevator, a seating area, and a dining space.
A hotel room with a bed, a sofa with cushions, a large window with a view of a cityscape and water.
A bar with a circular liquor display, seating with stools, and a city view through large windows.

6. Hyatt Regency Chicago

Hyatt Regency Chicago
Downtown Chicago
AU$387
includes taxes & fees
7 Sept - 8 Sept
Hyatt Regency Chicago
A modern building with the name 'SENIORAL' prominently displayed on the facade.
A balcony with a glass railing, a table, and four chairs.
A bar area with stools, a counter with bottles, and a wall with a leafy design.
A modern kitchen with a large island, bar stools, and a view of the city skyline.

7. Sentral Michigan Avenue

Sentral Michigan Avenue
Downtown Chicago
AU$290
includes taxes & fees
7 Sept - 8 Sept
Sentral Michigan Avenue
An outdoor seating area with wicker chairs, a glass-top table, and a sofa with cushions.
The exterior of the Hyatt Centric The Loop hotel with a prominent American flag, a classic facade, and a glass entrance.
A conference room with a long table, chairs, and a projector screen.
A gym with multiple treadmills aligned in rows, a cityscape mural on the wall, and a view of the water outside.

8. Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
Downtown Chicago
AU$352
includes taxes & fees
7 Sept - 8 Sept
Hyatt Centric The Loop Chicago
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.
A row of sun loungers with umbrellas, a glass building in the background, and a palm tree.
Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.
A modern hotel lobby with seating areas, a bar, and a display of beverages.

9. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
Downtown Chicago
AU$252
includes taxes & fees
9 Sept - 10 Sept
DoubleTree by Hilton Chicago - Magnificent Mile
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.
A modern hotel lobby with a marble floor, seating areas, and a ceiling with a sky-like projection.
A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.

10. The Wade

The Wade
Downtown Chicago
  • Luxurious lakeside retreat in city centre Chicago offers pillowtop beds, designer toiletries, and stunning views near Michigan Avenue.
AU$280
includes taxes & fees
7 Sept - 8 Sept
The Wade
View all properties

Top South Side Hotel Reviews

Carlton Inn Midway

Carlton Inn Midway

10/10 Excellent
"It’s very Good, good location, good parking, good room and good employees"
Icaro 1-night trip
Posted 6 hours ago
Carlton Inn Midway
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

8/10 Good
"The hotel was really nice and the rooms are clean and nice looking. Also only a 5-7 minutes walk from the Metra station and the bus station that gets you downtown pretty easily. Overall it was a really nice and located in a safe neighbourhood. The only negative about this place was that the wi-fi was very slow and sometime it did not work."
Martin 6-night trip
Posted 10 hours ago
Chicago Lake Shore Hotel
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

8/10 Good
"Staff"
Amy 3-night trip
Posted 11 hours ago
Holiday Inn Chicago – Midway Airport S by IHG
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"This hotel is well kept. The staff is very nice and helpful. There is good food near by and at night it's quiet. I didnt realize that our window faced the front of the building until the last day. Thats how quiet it was. Parking, like every major city, SUCKS. PAY THE METER."
Adama 3-night trip
Posted 2 days ago
Hyatt Place Chicago-South/University Medical Center
Chicago Marriott Midway

Chicago Marriott Midway

10/10 Excellent
"."
sindy 1-night trip
Posted 3 days ago
Chicago Marriott Midway

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