An airplane exhibit labeled "Concourse A" in an airport terminal.

Search Luxury Hotels in Southwest 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 Southwest Side Luxury Hotels

Our top choices for Southwest Side luxury hotels

A rooftop bar with seating and a view of the city skyline at night.

1. The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,000 reviews)
  • cleanliness
    Unwind in Chicago's premier luxury hotel with a full-service spa, indoor pool, and 2 exquisite restaurants in a prime location.
The price is ₹49,481
₹58,827 total
includes taxes & fees
13 Dec - 14 Dec
The Peninsula Chicago
A couple dining at a table with a view of a cityscape and a sunset.

2. Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,000 reviews)
  • cleanliness
    Indulge in sophisticated luxury at this Art Deco hotel featuring a full-service spa, indoor pool, and al fresco dining in City centre Chicago.
The price is ₹39,968
₹47,518 total
includes taxes & fees
15 Dec - 16 Dec
Park Hyatt Chicago
A person sitting by a window with a view of a cityscape, including a tall tower.

3. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (999 reviews)
  • cleanliness
    Indulge in sophisticated luxury at this five-star Chicago retreat with a full-service spa, heated indoor pool, and newly renovated spaces.
The price is ₹40,438
₹48,077 total
includes taxes & fees
15 Dec - 16 Dec
Four Seasons Hotel Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.

4. The St. Regis Chicago

The St. Regis Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (136 reviews)
  • cleanliness
    City centre Chicago's newest luxury icon offers indulgent spa treatments, fine dining, and poolside relaxation steps from Millennium Park.
The price is ₹53,062
₹63,085 total
includes taxes & fees
3 Dec - 4 Dec
The St. Regis Chicago
A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.

5. The Langham, Chicago

The Langham, Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,000 reviews)
  • cleanliness
    Indulge in refined riverside luxury at this Chicago hotel with deep-soaking tubs, a seven-treatment-room spa, and exceptional service.
The price is ₹40,998
₹48,743 total
includes taxes & fees
13 Dec - 14 Dec
The Langham, Chicago
A cityscape with a river, a bridge, and a dining area with tables and chairs.

6. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (2,076 reviews)
  • cleanliness
    Immerse in riverside elegance at this 5-star Chicago hotel offering deep-soaking tubs, pillowtop beds, and full-service spa indulgence.
The price is ₹37,029
₹44,024 total
includes taxes & fees
14 Dec - 15 Dec
Trump International Hotel & Tower Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.

7. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    City centre Chicago luxury at the Ritz-Carlton offers spa, pool, and Italian steakhouse near Michigan Avenue.
The price is ₹34,990
₹41,599 total
includes taxes & fees
13 Dec - 14 Dec
The Ritz-Carlton, Chicago
A rooftop terrace with a city skyline view, featuring a mix of modern and classic architecture, and several potted plants.

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

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,000 reviews)
  • cleanliness
    The Gwen invites travellers to indulge in city centre Chicago luxury with rooftop terrace and Mediterranean dining experiences.
The price is ₹28,760
₹36,996 total
includes taxes & fees
13 Dec - 14 Dec
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.

9. Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,001 reviews)
  • cleanliness
    Indulge in urban sophistication at this 5-star Chicago retreat, where spa treatments, poolside relaxation, and Art Deco elegance await.
The price is ₹41,257
₹49,051 total
includes taxes & fees
13 Dec - 14 Dec
Waldorf Astoria Chicago
A modern hotel room with a large window offering a city view, a wooden desk with a laptop, and a small seating area.

10. Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (968 reviews)
  • cleanliness
    Indulgent Chicago escape featuring upscale dining, indoor pool, and a tranquil steam room in the heart of downtown's vibrant atmosphere.
The price is ₹31,316
₹39,583 total
includes taxes & fees
26 Nov - 27 Nov
Nobu Hotel Chicago
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

Top Southwest Side Hotel Reviews

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Friendly staff, great location. Will be booking again"
Priscilla 3-night trip
Posted less than an hour ago
Eurostars Magnificent Mile

Explore a world of travel with Expedia