Are there any 5-star all-inclusive resorts in Chicago?

Expedia's filter tool is the easiest way to narrow down what you want. Select "5-star" and "All inclusive" to see the most upscale resorts in Chicago where your room, meals, activities and entertainment are included in the price. At these retreats, your trip is pure extravagance from the moment you enter the lobby.

What are the top 5-star spa hotels in Chicago?

Spoil yourself with decadent massages and other restorative treatments at The Peninsula Chicago . It's among Chicago's most impressive 5-star spa properties. Trump International Hotel & Tower Chicago and The Langham, Chicago also combine high-end accommodations with wellness activities.

Are there any 5-star vacation rentals in Chicago?

Our site doesn't offer any 5-star vacation rentals in Chicago. However, you will still find some top-rated stays where the only item on your itinerary will be to kick back and enjoy yourself. See what's available by searching through our vacation rentals in Chicago .

Are there any 5-star hotels in downtown Chicago?

Book a room at The Langham, Chicago . This 5-star hotel is perfect if you want to immerse yourself in Chicago's lively downtown scene.

5 Stars Hotels in Chicago: Compare Hotel Prices & Find the Cheapest Chicago, Illinois 5 Stars Hotels

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Our top choices for Chicago 5-star hotels

A person sitting by a window with a view of a cityscape, including a tall tower.

1. Four Seasons Hotel Chicago

Downtown Chicago

ryan

NT$19,186 total

includes taxes & fees

Nov 22 - Nov 23

A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.

2. Trump International Hotel & Tower Chicago

Downtown Chicago

Cecille

NT$17,870 total

includes taxes & fees

Nov 8 - Nov 9

A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.

3. The Peninsula Chicago

Downtown Chicago

Vincent Haley

NT$24,214 total

includes taxes & fees

Nov 23 - Nov 24

A modern hotel lobby with a reception desk, seating area, and large windows offering city views.

4. The Langham, Chicago

Downtown Chicago

Saramae

NT$20,232 total

includes taxes & fees

Nov 22 - Nov 23

A hotel entrance with a fountain, a car, and a person standing by the entrance.

5. Waldorf Astoria Chicago

Downtown Chicago

Luis

NT$18,943 total

includes taxes & fees

Nov 22 - Nov 23

A rooftop lounge with outdoor seating, a fire pit, and a large reflective sculpture.

6. The Ritz-Carlton, Chicago

Downtown Chicago

Krikour

NT$14,964 total

includes taxes & fees

Nov 25 - Nov 26

A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.

7. Nobu Hotel Chicago

Downtown Chicago

Abhay

NT$13,954 total

includes taxes & fees

Nov 23 - Nov 24

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.

8. Park Hyatt Chicago

Downtown Chicago

Tom

NT$17,957 total

includes taxes & fees

Nov 23 - Nov 24

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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.

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

NT$6,897

NT$8,096 total

Nov 27 - Nov 28

includes taxes & fees

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Pool Spa Hot tub Breakfast included Waterpark

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.

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

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Frequently asked questions

What are the best 5-star hotels in Chicago?

Based on Expedia guest reviews, The Langham, Chicago, Trump International Hotel & Tower Chicago and The Peninsula Chicago are among the best 5-star hotels in Chicago. Providing top-quality amenities and unmatchable service, you'll enjoy an indulgent and memorable stay.

How much does it cost to stay in a 5-star hotel in Chicago?

You'll find many different pricing options for a 5-star hotel in Chicago on Expedia. The amount you pay will depend on your vacation dates, length of stay and other factors. Compare all of the available accommodations for your chosen dates and use our pricing and other filters to discover the perfect luxury stay.

Search for the lowest price per night from NT$4,494

What makes a hotel 5 stars in Chicago?

Flawless guest service characterizes every 5-star hotel in Chicago. From the minute you arrive, staff are at your beck and call, whether arranging customized tours or providing in-room massage treatments. What's more, hotels must offer upscale conveniences to qualify for a 5-star rating. These can include luxury bathrobes, a wellness center, swimming pools, gourmet kitchens and knowledgeable concierge.

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