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

Compare and book 5 Star hotels in Hillside, Chicago

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Check availability on Hillside 5 Star Hotels

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Hillside 5-star hotels

A person sitting by a window with a view of a cityscape, including a tall tower.
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.
An indoor swimming pool with a skylight, a lifeguard chair, and a potted plant.

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
Downtown Chicago
United States
Edda
£473
includes taxes & fees
1 Nov - 2 Nov
Four Seasons Hotel Chicago
A cityscape with a river, a bridge, and a dining area with tables and chairs.
A modern hotel room with large windows, white furniture, and a view of tall buildings.
A modern hotel room with large floor-to-ceiling windows offering a city view.
A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
Downtown Chicago
United States
Cecille
£415
includes taxes & fees
1 Nov - 2 Nov
Trump International Hotel & Tower Chicago
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.
A modern hotel room with a large window offering a city view, three armchairs arranged around a central coffee table, and a decorative hanging plant.
A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.
A modern dining area with round tables, comfortable chairs, and a dessert display.

3. The Langham, Chicago

The Langham, Chicago
Downtown Chicago
United States
Saramae
£507
includes taxes & fees
1 Nov - 2 Nov
The Langham, Chicago
A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.
A rooftop bar with seating and a view of the city skyline at night.
A modern indoor pool area with large windows, potted palm plants, and lounge chairs.
A modern bar area with a checkered floor, bar stools, and a bartender.

4. The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago
United States
Levi
£585
includes taxes & fees
1 Nov - 2 Nov
The Peninsula Chicago
A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.
A bar area with a long counter, multiple stools, and a seating area with a booth.
A couple dining on a balcony with a cityscape view.
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.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
Downtown Chicago
United States
Luis
£486
includes taxes & fees
1 Nov - 2 Nov
Waldorf Astoria Chicago
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 offering a city view, a wooden desk with a laptop, and a small seating area.
A rooftop terrace with a view of a city skyline at dusk.
A modern lobby with a sofa, a coffee table, and a vase of flowers.

6. Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago
United States
Abhay
£428
includes taxes & fees
1 Nov - 2 Nov
Nobu Hotel Chicago
A couple dining at a table with a view of a cityscape and a sunset.
A woman sitting by a window with a city view, holding a cup and saucer.
A rooftop terrace with a dining table, chairs, and a view of the cityscape, including the Water Tower Place building.
A modern hotel room with a large bed, a seating area, a TV, and a view of the city and ocean.

7. Park Hyatt Chicago

Park Hyatt Chicago
Downtown Chicago
United States
Tom
£499
includes taxes & fees
1 Nov - 2 Nov
Park Hyatt Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.
A modern bar area with a central bar, multiple seating options, and a large chandelier.
A modern lobby with a central seating area, large windows, and a decorative ceiling feature.
A rooftop lounge with outdoor seating, a fire pit, and a large reflective sculpture.

8. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
Downtown Chicago
£455
includes taxes & fees
1 Nov - 2 Nov
The Ritz-Carlton, Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.
A rooftop pool area with city views, two lounge chairs, and a small table with a vase.
A modern hotel entrance with a prominent "STREGIS" sign, large glass windows, and a well-lit facade.
A modern hotel lobby with a large seating area, a view of the city, and a green accent wall.

9. The St. Regis Chicago

The St. Regis Chicago
Downtown Chicago
United States
Xiomara
£499
includes taxes & fees
12 Nov - 13 Nov
The St. Regis Chicago
A rooftop lounge with a city skyline view, featuring a sofa set with patterned cushions and a table with drinks and snacks.
A coastal city skyline with modern high-rise buildings, a beach, and a clear blue sky.
A living room with a fireplace, a mounted TV displaying Netflix content, and a staircase leading to another level.
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island with bar stools.

10. Art Villa

Art Villa
West Town
Art Villa
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Hillside.
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
£137
25 Oct - 26 Oct
includes taxes & fees
River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

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£128
9 Nov - 10 Nov
includes taxes & fees
8/10 Very good! (2,492 reviews)
The Chicago Hotel Collection Ambassador Gold Coast
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

172 W Adams St Chicago IL
£161
25 Oct - 26 Oct
includes taxes & fees
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
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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.

Learn more about Hillside

This small village offers a peaceful escape with its charming Hillside Park and community events throughout the year. Grab a bite at local family restaurants before exploring nearby Forest Park's beautiful Concordia Cemetery or Oak Park's Frank Lloyd Wright attractions.

See all hotels in Hillside
A lush green valley with a winding road, steep mountains, and a misty atmosphere.

Top Hillside Hotel Reviews

Find out more about Hillside

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Hillside?
The amount you pay for a 5-star hotel in Hillside depends on things such as when you plan to travel and the length of your escape. Our top tip for landing an awesome deal? Use our pricing filters to check out the available hotels for your chosen dates.
  • Search for the lowest price per night from £128
What makes a hotel 5 stars in Hillside?
Faultless guest service characterises every 5-star hotel in Hillside. From the instant you arrive, staff cater to your every need, whether arranging customised tours or providing in-room massages. On top of that, hotels must offer superior conveniences to be entitled to a 5-star rating. These can include luxury toiletries, spas or saunas, swimming pools, gourmet kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Hillside?
Our convenient filters are the best way to narrow down what you want. Check the "All inclusive" and "5-star" boxes to see the most upscale resorts in Hillside where your accommodation, meals, activities and entertainment are included in the upfront price. At these stays, your holiday is pure extravagance from the moment you enter the lobby.

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