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 NZ$186

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Check availability on South Side Luxury Hotels

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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 spacious living area with a modern chandelier, comfortable seating, and a fireplace.
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.

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.
NZ$641
includes taxes & fees
30 Oct - 31 Oct
Sophy Hyde Park
A large, historic building with a central courtyard surrounded by trees.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.

2. Hilton Chicago

Hilton Chicago
Downtown Chicago
NZ$400
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.
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.
A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

3. The Wade

The Wade
Downtown Chicago
  • Luxurious lakeside retreat in city centre Chicago offers pillowtop beds, designer toiletries, and stunning views near Michigan Avenue.
NZ$313
includes taxes & fees
25 Oct - 26 Oct
The Wade
A modern building with the name 'SENIORAL' prominently displayed on the facade.
A bar area with stools, a counter with bottles, and a wall with a leafy design.
A balcony with a glass railing, a table, and four chairs.
A modern kitchen with a large island, bar stools, and a view of the city skyline.

4. Sentral Michigan Avenue

Sentral Michigan Avenue
Downtown Chicago
NZ$415
includes taxes & fees
26 Oct - 27 Oct
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 grilled pineapple on top of a stack of meat, served on a pan.
A gym with multiple treadmills aligned in rows, a cityscape mural on the wall, and a view of the water outside.

5. Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
Downtown Chicago
NZ$609
includes taxes & fees
29 Oct - 30 Oct
Hyatt Centric The Loop Chicago
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
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.
A modern living room with a large window overlooking a body of water, a tripod, and a sofa.

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

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
NZ$632
includes taxes & fees
29 Oct - 30 Oct
Sable at Navy Pier Chicago, Curio Collection by Hilton
A spacious lobby with a central coffee table, sofas, and a large mirror.
A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.
A spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.
A spacious lobby with high ceilings, large arched windows, and a grand staircase.

7. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
NZ$376
includes taxes & fees
26 Oct - 27 Oct
The Chicago Hotel Collection Ambassador Gold Coast
A historic building with ornate architecture, large arched windows, and a prominent Blackstone sign.
A luxurious lobby with a blue sofa, a black entertainment unit, and artwork on the walls.
A luxurious room with a fireplace, two armchairs, a coffee table, and a large mirror.
A grand staircase with blue carpet and gold railings leading to a store named 'Mercat'.

8. The Blackstone, Autograph Collection

The Blackstone, Autograph Collection
Downtown Chicago
NZ$585
includes taxes & fees
25 Oct - 26 Oct
The Blackstone, Autograph Collection
A modern kitchen with a marble island, fruit bowls, and a city view.
A Fairmont hotel with a prominent entrance, large windows, and a sculpture on the facade.
A modern bar area with a central bar, seating, and a distinctive ceiling design.
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.

9. Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
Downtown Chicago
NZ$489
includes taxes & fees
30 Oct - 31 Oct
Fairmont Chicago at Millennium Park
An outdoor rooftop lounge with seating, a fire feature, and a view of the city skyline at night.
A rooftop venue with white chairs and a sofa, draped with white fabric and floral arrangements, overlooking a cityscape.
The Chicago Hotel Collection building with a glass facade, American flag, and signage for Barista Bar and Seighity events.
A modern lounge area with leather sofas, wooden coffee tables, and ambient lighting.

10. The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
Downtown Chicago
NZ$338
includes taxes & fees
29 Oct - 30 Oct
The Chicago Hotel Collection - Magnificent Mile
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Top South Side Hotel Reviews

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

8/10 Good
"Good"
josefina 1-night trip
Posted 2 hours ago
Holiday Inn Chicago – Midway Airport S by IHG
Carlton Inn Midway

Carlton Inn Midway

10/10 Excellent
"The room was lovely and clean, breakfast was good, staff was very pleasant"
Elaine 2-night trip
Posted 14 hours ago
Carlton Inn Midway
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

10/10 Excellent
"Good"
Balaji 1-night trip
Posted 1 day ago
Chicago Lake Shore Hotel
Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport

10/10 Excellent
"Rooms very clean. Staff very friendly and helpful… will definitely stay here again"
susan 1-night trip
Posted 7 days ago
Best Western Inn & Suites - Midway Airport

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