A lush green valley with a winding road, steep mountains, and a misty atmosphere.

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Check availability on Hillside Luxury Hotels

Tonight
24 Oct - 25 Oct
Tomorrow
25 Oct - 26 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

Our top choices for Hillside luxury hotels

A modern building with a glass facade and a sign reading "Le MERIDIEN".
A modern lobby with contemporary furniture, a large abstract mural, and a glass coffee table.
An outdoor patio area with tables and chairs, umbrellas, and a fire pit.
A restaurant with yellow chairs, wooden tables, and a bar area in the background.

1. Le Méridien Chicago - Oakbrook Center

Le Méridien Chicago - Oakbrook Center
Oak Brook
  • Luxurious escape with spa indulgence and dining excellence awaits at this Oak Brook hotel connected to upscale shopping.
₹16,150
₹17,600 total
includes taxes & fees
30 Oct - 31 Oct
Le Méridien Chicago - Oakbrook Center
A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.
A modern indoor pool area with large windows, potted palm plants, and lounge chairs.
A rooftop bar with seating and a view of the city skyline at night.
A spacious hotel lobby with multiple seating areas, a grand staircase, and large windows offering views of the city.

2. The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago
  • Unwind in Chicago's premier luxury hotel with a full-service spa, indoor pool, and 2 exquisite restaurants in a prime location.
₹59,339
₹70,548 total
includes taxes & fees
15 Nov - 16 Nov
The Peninsula Chicago
A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.
A cityscape with a river, a bridge, and a dining area with tables and chairs.
A modern hotel room with large floor-to-ceiling windows offering a city view.
A pool area with a view of a cityscape, a lounge with wicker furniture, and a person relaxing in the pool.

3. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
Downtown Chicago
  • Immerse in riverside elegance at this 5-star Chicago hotel offering deep-soaking tubs, pillowtop beds, and full-service spa indulgence.
₹43,739
₹52,001 total
includes taxes & fees
23 Nov - 24 Nov
Trump International Hotel & Tower Chicago
A multi-story hotel with a prominent "WESTIN" sign on the top.
A terrace with round tables and chairs, a view of a lake, and a building with a white facade.
A long corridor with a patterned carpet, large windows, and a bench on the left.
A spacious lobby with a central seating area, large wooden columns, and potted plants.

4. The Westin Chicago Lombard

The Westin Chicago Lombard
Lombard
  • Luxury pillow-top beds, refined dining, and pool relaxation define this 4-star Chicago hotel near premier shopping.
₹11,583
₹12,855 total
includes taxes & fees
22 Nov - 23 Nov
The Westin Chicago Lombard
A long, narrow hallway with a patterned carpet, recessed lighting, and doors on one side.
A modern bar area with a curved ceiling, wooden slats, and a bar counter with stools.
Exterior
A restaurant interior with a stone accent wall, a bar area, and a seating section.

5. Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel
Rosemont
  • Indulgent urban oasis near Rosemont Theatre offers luxury comforts with Frette Italian sheets, rainfall showers, and designer amenities.
₹14,146
₹16,124 total
includes taxes & fees
23 Nov - 24 Nov
Loews Chicago O'Hare Hotel
A rooftop lounge with outdoor seating, a fire pit, and a large reflective sculpture.
A spacious lobby with a central seating area, a reception desk, and a large chandelier.
A modern lobby with a central seating area, large windows, and a decorative ceiling feature.
A modern bar area with a central bar, multiple seating options, and a large chandelier.

6. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
Downtown Chicago
  • City centre Chicago luxury at the Ritz-Carlton offers spa, pool, and Italian steakhouse near Michigan Avenue.
₹35,247
₹41,906 total
includes taxes & fees
22 Nov - 23 Nov
The Ritz-Carlton, Chicago
A person sitting by a window with a view of a cityscape, including a tall tower.
A group of people on a boat with a city skyline in the background.
A couple walking through a spacious lobby with marble flooring, large white floral arrangements, and a modern staircase in the background.
A modern bar area with a central bar and multiple stools, surrounded by a high ceiling with a decorative light fixture.

7. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
Downtown Chicago
  • Indulge in sophisticated luxury at this five-star Chicago retreat with a full-service spa, heated indoor pool, and newly renovated spaces.
₹45,572
₹54,181 total
includes taxes & fees
22 Nov - 23 Nov
Four Seasons Hotel Chicago
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.
A swimming pool with a ceiling of lights, large windows, and potted plants.
A modern dining area with round tables, comfortable chairs, and a dessert display.
A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.

8. The Langham, Chicago

The Langham, Chicago
Downtown Chicago
  • Indulge in refined riverside luxury at this Chicago hotel with deep-soaking tubs, a seven-treatment-room spa, and exceptional service.
₹49,560
₹58,922 total
includes taxes & fees
22 Nov - 23 Nov
The Langham, Chicago
A hotel entrance with a fountain, a car, and a person standing by the entrance.
A bar area with a long counter, multiple stools, and a seating area with a booth.
An indoor swimming pool with a modern design, a reception area with a sign for Waldorf Astoria Chicago, and a seating area with two people.
A couple dining on a balcony with a cityscape view.

9. Waldorf Astoria Chicago

Waldorf Astoria Chicago
Downtown Chicago
  • Indulge in urban sophistication at this 5-star Chicago retreat, where spa treatments, poolside relaxation, and Art Deco elegance await.
₹46,403
₹55,169 total
includes taxes & fees
22 Nov - 23 Nov
Waldorf Astoria Chicago
A modern living room with a sofa, chairs, a coffee table, and a TV. A large window offers a view of a cityscape and a tower.
A modern hotel room with a large bed, a seating area, a TV, and a view of the city and ocean.
A couple dining at a table with a view of a cityscape and a sunset.
A rooftop terrace with a dining table, chairs, and a view of the cityscape, including the Water Tower Place building.

10. Park Hyatt Chicago

Park Hyatt Chicago
Downtown Chicago
  • Indulge in sophisticated luxury at this Art Deco hotel featuring a full-service spa, indoor pool, and al fresco dining in City centre Chicago.
₹44,006
₹52,319 total
includes taxes & fees
22 Nov - 23 Nov
Park Hyatt Chicago
View all properties

Top Hillside Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Shower pressure could be much better!"
Brandi 3-night trip
Posted 1 hour ago
The Royal Sonesta Chicago Downtown
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Great place to stay! Cool rooftop."
Amber 1-night trip
Posted 1 hour ago
The Chicago Hotel Collection - Magnificent Mile
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Amazing all the way around!!!"
Ruben 1-night trip
Posted 2 hours ago
Congress Plaza Hotel
The Wade

The Wade

8/10 Good
"I don’t know if this is normal but u can always hear the elevator all night long going up and down, Beds are hard, not my ting"
Maximiliano 2-night trip
Posted 3 hours ago
The Wade
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

10/10 Excellent
"Buena ubicación y precio"
Jonathan 1-night trip
Posted 5 hours ago
Hotel Saint Clair- Magnificent Mile
Warwick Allerton - Chicago

Warwick Allerton - Chicago

10/10 Excellent
"The mattress was a little uncomfortable and pillows to high and small, but otherwise good."
Vivian 1-night trip
Posted 16 hours ago
Warwick Allerton - Chicago

Frequently asked questions

Are you searching for a great accommodation for your luxury getaway to Hillside?
Expedia can help you get a flight to Chicago O'Hare International Airport (ORD) airport or Chicago Midway Airport (MDW) airport, and then you can select from a variety of places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Hillside offers. During your visit, you might want to enjoy the restaurants which Hillside is known for.
When can I expect good weather in Hillside?
Planning for the weather is an important factor for making your trip to Hillside a success, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillside are January, November, February and December, with each month seeing an average of 13 cm of snowfall.
What's there to see and do in Hillside?
When you're in Hillside, enjoy exploring the sights and attractions here including Wrigley Field, Soldier Field and Navy Pier. If you have extra time while you're in the area, you might want to stop by United Center and Michigan Avenue.

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