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 accommodation with wellness activities.

Are there any 5-star holiday rentals in Chicago?

Our site doesn't offer any 5-star holiday 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 holiday 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.

TOP 10 Luxurious 5 Star Hotels in Chicago for 2026

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Our top choices for Chicago 5-star hotels

Four Seasons Hotel Chicago

Downtown Chicago

lora

includes taxes & fees

11 Jun - 12 Jun

The Langham, Chicago

Downtown Chicago

Simon

includes taxes & fees

11 Jun - 12 Jun

Trump International Hotel & Tower Chicago

Downtown Chicago

Mamta Singh

includes taxes & fees

25 May - 26 May

The Peninsula Chicago

Downtown Chicago

Caron

includes taxes & fees

24 May - 25 May

Waldorf Astoria Chicago

Downtown Chicago

Shante

includes taxes & fees

25 May - 26 May

The Ritz-Carlton, Chicago

Downtown Chicago

Geneva

includes taxes & fees

24 May - 25 May

Breakfast, lunch, dinner served; American cuisine, al fresco dining

Park Hyatt Chicago

Downtown Chicago

Kerry

includes taxes & fees

25 May - 26 May

Indoor pool, open 6:00 AM to 9:00 PM, pool loungers

Nobu Hotel Chicago

Downtown Chicago

Kathryn

includes taxes & fees

25 May - 26 May

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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

S$380

23 May - 24 May

includes taxes & fees

8.4/10 Very Good! (2,310 reviews)

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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.

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Stay in Luxury: 5 Star Hotels in Chicago

There's nothing wrong with enjoying the finer things in life. Indulge your every desire on your upcoming leisure time. Treat yourself with a stay in a 5-star hotel during your Chicago trip. You'll join the multitudes of holidaymakers who have made Chicago so fashionable recently. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Reserve one of our 5-star hotels in Chicago and indulge in the finer things in life for a while.

5-Star Hotels in Chicago

You'll have a wonderful time at one of these 5-star hotels. Exceptional customer care, luxurious bedding, and deeply relaxing spa offerings are waiting for you. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready for a wonderful adventure. What kind of amenities will make your stay a wonderful one? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A body scrub that will leave you feeling refreshed and alive? Butler services? Whatever it is your heart desires, you're bound to find it here. Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs.

But you aren't going to spend your entire holiday in your room, of course. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Chicago are waiting for you to relax after an exciting day.

Make Your Escape

The results are in, and Chicago 5-star hotels are the place to be when you book your next holiday. If you've been dreaming about a holiday set here, then go ahead and book it. It's time to plan your next great escape -- this is a great time to find 5-star hotel deals in Chicago! Choose one of our Chicago 5-star hotels today and soothe yourself in luxe surroundings at your convenience.

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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 holiday dates, length of stay and other factors. Compare all of the available accommodation 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 S$263

What makes a hotel 5 stars in Chicago?

Flawless guest service chatacterises every 5-star hotel in Chicago. From the minute you arrive, staff are at your beck and call, whether arranging customised 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 centre, swimming pools, gourmet kitchens and knowledgeable concierge.

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