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Luxury Hotels & Resorts in Southwest Side from AU$129

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Check availability on Southwest Side Luxury Hotels

Tonight
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Southwest Side luxury hotels

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 rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

1. 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$217
includes taxes & fees
1 Nov - 2 Nov
The Wade
A modern reception area with a marble reception desk, a sofa, armchairs, and a coffee table.
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.
A historic building with large windows and a marquee sign for a hotel.

2. JW Marriott Chicago

JW Marriott Chicago
Downtown Chicago
  • Spa indulgence awaits in city centre Chicago where luxurious treatments and premium dining create memorable moments.
AU$486
includes taxes & fees
30 Oct - 31 Oct
JW Marriott Chicago
A modern hotel room with large windows, a sofa, chairs, a dining table, and a coffee table.
An outdoor seating area with sofas, chairs, and tables, surrounded by trees and string lights.
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.

3. 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$452
includes taxes & fees
31 Oct - 1 Nov
Sophy Hyde Park
A dining table set for six with a cityscape view through large windows.
A modern hotel room with a large window offering a city skyline view, a round table with four chairs, and a ceiling with recessed lighting.
A modern hotel room with a large window offering a cityscape view, a green sofa, two armchairs, and a coffee table with flowers.
The exterior of the Swissotel building with its distinctive glass facade and the hotel's name displayed prominently.

4. Swissotel - Chicago

Swissotel - Chicago
Downtown Chicago
AU$378
includes taxes & fees
31 Oct - 1 Nov
Swissotel - Chicago
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 modern lounge with a fireplace, comfortable seating, and large windows offering city views.
A spacious lobby with a large window, a central floral arrangement, and modern seating.

5. 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.
AU$431
includes taxes & fees
30 Oct - 31 Oct
theWit Chicago, a Hilton Hotel
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 modern bar area with a central bar, seating, and a distinctive ceiling design.
A Fairmont hotel with a prominent entrance, large windows, and a sculpture on the facade.

6. Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
Downtown Chicago
AU$341
includes taxes & fees
31 Oct - 1 Nov
Fairmont Chicago at Millennium Park
A bar area with a long counter, multiple bar stools, and a wall of bookshelves.
A marble-floored hallway with a central archway, flanked by columns and modern lighting fixtures.
A modern indoor lounge area with seating, a coffee table, and potted plants.
A spacious lobby with a glass ceiling, seating areas, and a reception desk.

7. Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG
Downtown Chicago
  • Luxurious Chicago escape with exceptional service delivers refined comfort and deep-soaking tubs in the heart of city centre.
AU$493
includes taxes & fees
25 Oct - 26 Oct
Kimpton Gray Hotel by IHG
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.
A modern hotel room with a desk, a sofa, a coffee machine, a TV, and a unique wall art piece.
A modern living room with a sofa, coffee table, and ottoman, a fireplace, and a large window with a city view.
A modern room with a view of a river and high-rise buildings.

8. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
  • Unwind in city centre Chicago's LondonHouse with rejuvenating spa treatments and riverfront luxury.
AU$474
includes taxes & fees
1 Nov - 2 Nov
LondonHouse Chicago, Curio Collection by Hilton
A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.
A modern hotel room with a large window, a wooden desk, a bathroom with a mirror, and a view of the cityscape.
A modern lobby with a sofa, a coffee table, and a vase of flowers.
A modern hotel room with a large window offering a city view, a wooden desk with a laptop, and a small seating area.

9. Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago
  • Indulgent Chicago escape featuring upscale dining, indoor pool, and a tranquil steam room in the heart of downtown's vibrant atmosphere.
AU$814
includes taxes & fees
1 Nov - 2 Nov
Nobu Hotel 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 modern lobby with a bar area, plush seating, and a chandelier.
A hotel entrance with a sign reading "The Lasalle Hotel" and a "Grill on 21" sign.

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.
AU$565
includes taxes & fees
30 Oct - 31 Oct
The LaSalle Chicago, Autograph Collection by Marriott
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Top Southwest Side Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Hotel was very clean, grateful housekeeping came in everyday and provided clean towels. Room view was very nice and as advertised."
Erica 4-night trip
Posted 5 hours ago
The Royal Sonesta Chicago Downtown
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

10/10 Excellent
"Staff was very helpful"
Bryce 1-night trip
Posted 6 hours ago
Hotel Saint Clair- Magnificent Mile
Central Loop Hotel

Central Loop Hotel

10/10 Excellent
"I liked the location and staff"
Murray 1-night trip
Posted 7 hours ago
Central Loop Hotel
Hilton Chicago

Hilton Chicago

10/10 Excellent
"Convenient location walk to anything you might need, restaurants, shopping, Room was so nice and comfortable"
Jenessa 1-night trip
Posted 9 hours ago
Hilton Chicago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"If I could give more than 5 stars I would. The staff was amazing and extremely accommodating and flexible. The rooms were gorgeous and the hotel was beautiful."
Afra 1-night trip
Posted 16 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Traveling cross country and stayed at several hotel. This one was on point, from entering the hotel, smelling clean, the staff checking in was great, and the room was clean. I had an awesome stay."
Jose 2-night trip
Posted 2 days ago
Hampton Inn Chicago Downtown/Magnificent Mile

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