A frozen river with a city skyline in the background.

5 Stars Hotels in Uptown, Chicago from CA $273

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Our top choices for Uptown 5-star hotels

Rooftop terrace

The Guesthouse Hotel

The Guesthouse Hotel
4.0 star property
Uptown
9.8 out of 10, Exceptional, (405 reviews)
"We had an excellent stay . The accommodations were so clean and comfortable and the staff made us feel so welcome and at home . We wouldn’t stay anywhere else if we travel to Chicago again ."
United States
Dianne
The Guesthouse Hotel
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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 Uptown.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
The price is CA $395 per night from Aug 2 to Aug 3
CA $395
CA $464 total
Aug 2 - Aug 3
includes taxes & fees
8.4/10 Very good! (2,342 reviews)
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Top Uptown Hotel Reviews

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Five Star Hotels in Uptown

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 Uptown 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 Uptown and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Uptown

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 Uptown

The results are in, and Uptown 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 Uptown! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Uptown today and settle down in the lap of luxury tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Uptown?
You'll find a range of pricing options for 5-star hotels in Uptown on Expedia. How much you'll pay will depend on when you want to travel, length of stay and other factors. Compare available accommodations for your chosen dates and make use of our pricing and other filters to discover the ideal luxury stay.

  • Search for the lowest price per night from CA $273

What makes a hotel 5 stars in Uptown?
Flawless guest service is the foundation of every 5-star hotel in Uptown. From the moment you enter the lobby, staff cater to your every whim, whether recommending activities or providing a turn-down service. Plus, hotels have to feature upscale conveniences to be eligible for a 5-star rating. These can include luxury toiletries, on-site spa facilities, pools, fine dining kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Uptown?
Use Expedia's filter tool to find a luxury getaway in Uptown where most of what you need is included. Next, refine your results for accommodations that have a rating of 5 stars and are described as "All inclusive." The most important thing on the to-do list at these stays? Relaxation and enjoyment.

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