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

Best Luxury Hotels in South Side

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on South Side Luxury Hotels

Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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.
An outdoor seating area with sofas, chairs, and tables, surrounded by trees and string lights.
A multi-story hotel with a modern design, featuring a prominent entrance with a marquee and outdoor seating area.

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.
RM933
RM1,215 total
includes taxes & fees
22 Nov - 23 Nov
Sophy Hyde Park
The Intercontinental hotel facade with a large American flag and a floral display.
A person sitting by a window with a cityscape view.
A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.
A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

2. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
  • Elegant city centre sanctuary boasts historic charm, luxury spa treatments, and a stunning indoor pool.
RM747
RM1,031 total
includes taxes & fees
22 Nov - 23 Nov
InterContinental Chicago Magnificent Mile by IHG
A modern reception area with a marble reception desk, a sofa, armchairs, and a coffee table.
A historic building with large windows and a marquee sign for a hotel.
A luxurious hotel lobby with marble columns, a polished floor, and ornate chandeliers.
A grand hotel lobby with a high ceiling, a large chandelier, and a staircase leading to an upper floor.

3. JW Marriott Chicago

JW Marriott Chicago
Downtown Chicago
  • Spa indulgence awaits in city centre Chicago where luxurious treatments and premium dining create memorable moments.
RM828
RM1,130 total
includes taxes & fees
22 Nov - 23 Nov
JW Marriott Chicago
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 lounge area with a central bar, seating arrangements, and a decorative chandelier.

4. Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
Downtown Chicago
RM975
RM1,305 total
includes taxes & fees
22 Nov - 23 Nov
Fairmont Chicago at Millennium Park
An outdoor seating area with modern furniture and potted plants.
A corridor with a brick wall, hanging wicker light fixture, and potted plants.
A modern skyscraper with a unique wavy facade, surrounded by other high-rise buildings.
A modern interior with a staircase, glass railings, and a visible restaurant area.

5. Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
Downtown Chicago
  • Indulgent city retreat offers a seasonal outdoor pool, indoor spa sanctuary, and breathtaking skyline views in city centre Chicago.
RM643
RM890 total
includes taxes & fees
22 Nov - 23 Nov
Radisson Blu Aqua Hotel Chicago
A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.
A bar area with a long counter, multiple shelves of bottles, and four bar stools.
A room with a bed, a window with curtains, a small table with a vase of flowers, and a chair.
A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.

6. L7 Chicago by LOTTE

L7 Chicago by LOTTE
Downtown Chicago
RM592
RM703 total
includes taxes & fees
22 Nov - 23 Nov
L7 Chicago by LOTTE
A spacious indoor area with a high ceiling, large windows, and a central seating area with sofas and tables.
A rooftop bar with seating areas, large windows, and a city view.
A spacious lobby with a large window, a central floral arrangement, and modern seating.
A bar area with a large TV screen, multiple shelves of bottles, and orange bar stools.

7. theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel
Downtown Chicago
  • Luxuriate in city centre Chicago at this full-service spa hotel steps from Michigan Avenue and the Riverwalk.
RM621
RM858 total
includes taxes & fees
22 Nov - 23 Nov
theWit Chicago, a Hilton Hotel
An outdoor seating area with sofas, tables, and umbrellas, overlooking a cityscape.
A hotel room with a large bed, a sofa, a TV, and a desk.
A modern lounge area with comfortable seating, a glass coffee table, and large windows offering a city view.
A modern living room with a flat-screen TV, a coffee table with books, a sofa, and a lamp.

8. The Westin Chicago River North

The Westin Chicago River North
Downtown Chicago
  • Riverside luxury with stellar Chicago Theatre views awaits at this city centre hotel.
RM812
RM1,111 total
includes taxes & fees
22 Nov - 23 Nov
The Westin Chicago River North
A rooftop terrace with a city skyline view, featuring a mix of modern and classic architecture, and several potted plants.
A modern hotel lobby with a reception desk, seating area, staircase, and large windows.
A modern staircase with glass railings and pendant lighting.
A modern hotel room with a green sofa, two round tables, a city view, and a chandelier.

9. The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Downtown Chicago
  • The Gwen invites travellers to indulge in city centre Chicago luxury with rooftop terrace and Mediterranean dining experiences.
RM1,141
RM1,478 total
includes taxes & fees
22 Nov - 23 Nov
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
A spacious lobby with a plush teal sofa, a round coffee table, and a large chandelier.
A grand staircase with a geometric patterned floor, marble walls, and a chandelier.
A hotel entrance with a sign reading "The Lasalle Hotel" and a "Grill on 21" sign.
A modern lobby with a bar area, plush seating, and a chandelier.

10. The LaSalle Chicago, Autograph Collection by Marriott

The LaSalle Chicago, Autograph Collection by Marriott
Downtown Chicago
  • Elegant city centre Chicago luxury with 24-hour fitness and upscale dining steps from Willis Tower.
RM1,061
RM1,261 total
includes taxes & fees
22 Nov - 23 Nov
The LaSalle Chicago, Autograph Collection by Marriott
View all properties

Top South Side Hotel Reviews

Carlton Inn Midway

Carlton Inn Midway

10/10 Excellent
"Clean room air conditioning staff"
Samy 1-night trip
Posted 6 hours ago
Carlton Inn Midway
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"Very clean and the staff were great."
Craig 1-night trip
Posted 20 hours ago
Hyatt Place Chicago-South/University Medical Center
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

8/10 Good
"I had several towels the had stains on them. Staff wasn’t always pleasant."
Lucretia 5-night trip
Posted 2 days ago
Holiday Inn Chicago – Midway Airport S by IHG

Explore a world of travel with Expedia