A river with a yellow boat, surrounded by tall buildings and a bridge.

5 Stars Hotels in Chicago, Illinois from CA $242

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Check availability on Chicago 5 Star Hotels

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Oct 1 - Oct 2
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Oct 2 - Oct 3
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Oct 2 - Oct 4
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Oct 9 - Oct 11

Our top choices for Chicago 5-star hotels

A person sitting by a window with a view of a cityscape, including a tall tower.
An indoor swimming pool with a skylight, a lifeguard chair, and a potted plant.
A group of people on a boat with a city skyline in the background.
A modern bar area with a central bar and multiple stools, surrounded by a high ceiling with a decorative light fixture.

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
Downtown Chicago
United States
Teresa
CA $754
CA $897 total
includes taxes & fees
Nov 1 - Nov 2
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 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.
A modern hotel room with large windows, white furniture, and a view of tall buildings.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
Downtown Chicago
United States
Mark
CA $657
CA $781 total
includes taxes & fees
Nov 1 - Nov 2
Trump International Hotel & Tower Chicago
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.
A modern dining area with round tables, comfortable chairs, and a dessert display.
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.

3. The Langham, Chicago

The Langham, Chicago
Downtown Chicago
United States
Saramae
CA $811
CA $965 total
includes taxes & fees
Oct 25 - Oct 26
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 bar area with a checkered floor, bar stools, and a bartender.
A modern indoor pool area with large windows, potted palm plants, and lounge chairs.

4. The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago
United States
Levi
CA $890
CA $1,058 total
includes taxes & fees
Nov 1 - Nov 2
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
CA $789
CA $938 total
includes taxes & fees
Nov 1 - Nov 2
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 modern lobby with a sofa, a coffee table, and a vase of flowers.
A modern hotel room with a large window, a wooden desk, a bathroom with a mirror, and a view of the cityscape.

6. Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago
United States
Abhay
CA $617
CA $770 total
includes taxes & fees
Oct 25 - Oct 26
Nobu Hotel Chicago
A couple dining at a table with a view of a cityscape and a sunset.
A modern hotel room with a large bed, a seating area, a TV, and a view of the city and ocean.
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 woman sitting by a window with a city view, holding a cup and saucer.

7. Park Hyatt Chicago

Park Hyatt Chicago
Downtown Chicago
United States
Tom
CA $782
CA $929 total
includes taxes & fees
Nov 1 - Nov 2
Park Hyatt Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.
A spacious lobby with a central seating area, a reception desk, and a large chandelier.
A modern bar area with a central bar, multiple seating options, and a large chandelier.
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
United States
Fred
CA $678
CA $806 total
includes taxes & fees
Nov 1 - Nov 2
The Ritz-Carlton, Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.
A modern hotel lobby with a large seating area, a view of the city, and a green accent wall.
A rooftop pool area with city views, two lounge chairs, and a small table with a vase.
A dining area with wicker chairs and tables, overlooking a marina with boats and a Ferris wheel.

9. The St. Regis Chicago

The St. Regis Chicago
Downtown Chicago
United States
Xiomara
CA $888
CA $1,056 total
includes taxes & fees
Oct 29 - Oct 30
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 Chicago.
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
CA $238
CA $283 total
Nov 1 - Nov 2
includes taxes & fees
River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
CA $204
CA $242 total
Nov 1 - Nov 2
includes taxes & fees
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
CA $282
CA $336 total
Oct 23 - Oct 24
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
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Chicago and related destinations

Towering skyscrapers frame the stunning Millennium Park where 'The Bean' reflects the city's vibrant energy. Cruise along the Chicago River for spectacular architecture views or catch a Cubs game at historic Wrigley Field.

See all hotels in Chicago
A river with a yellow boat, surrounded by tall buildings and a bridge.

Top Chicago Hotel Reviews

Find out more about Chicago

Five Star Hotels in Chicago

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Chicago so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Chicago and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Chicago

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Chicago

The results are in, and Chicago 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Chicago! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Chicago today and settle down in the lap of luxury tomorrow.

Frequently asked questions

What are the best 5-star hotels in Chicago?
The Langham, Chicago, Trump International Hotel & Tower Chicago and The St. Regis Chicago are some of the top 5-star hotels in Chicago, according to our traveller reviews. These upmarket hotels rate highly for things like their amenities, location and guest services. Select your favourite and experience the best of everything.
How much does it cost to stay in a 5-star hotel in Chicago?
The amount you pay for a 5-star hotel in Chicago can vary depending on the time of year you travel and how long you plan to be away, among several factors. Take advantage of our price per night filter and other search tools to find the best rate on a plush stay.
  • Search for the lowest price per night from CA $242
What makes a hotel 5 stars in Chicago?
Flawless guest service characterizes every 5-star hotel in Chicago. From the moment you arrive, staff attend to your every whim, whether arranging valet parking or providing in-room massages. Also, hotels have to feature superior conveniences to be eligible for a 5-star rating. These can include deluxe baths, a wellness centre, pools, gourmet kitchens and knowledgeable concierge.

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