Are there any 5-star holiday rentals in Uptown?

There are no 5-star holiday rentals in Uptown on our site, but there are a few other highly rated properties worth checking out. Scan through our holiday rentals in Uptown to book the ideal place for your stay.

5 Stars Hotels in Uptown: Special Rates & Discounts

A frozen river with a city skyline in the background.

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Check availability on Uptown 5 Star Hotels

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Our top choices for Uptown 5-star hotels

A hotel room with a bed, a seating area with a coffee table, a desk, and a view of the ocean.

1. Four Seasons Hotel Chicago

Downtown Chicago

Edda

HK$4,898 total

includes taxes & fees

1 Nov - 2 Nov

A cityscape with a river, a bridge, and a dining area with tables and chairs.

2. Trump International Hotel & Tower Chicago

Downtown Chicago

Cecille

HK$4,303 total

includes taxes & fees

1 Nov - 2 Nov

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

3. The Langham, Chicago

Downtown Chicago

Saramae

HK$5,076 total

includes taxes & fees

1 Nov - 2 Nov

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

4. The Peninsula Chicago

Downtown Chicago

Levi

HK$6,065 total

includes taxes & fees

1 Nov - 2 Nov

A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.

5. Waldorf Astoria Chicago

Downtown Chicago

Luis

HK$5,036 total

includes taxes & fees

1 Nov - 2 Nov

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

6. Nobu Hotel Chicago

Downtown Chicago

Abhay

HK$4,439 total

includes taxes & fees

1 Nov - 2 Nov

A couple dining at a table with a view of a cityscape and a sunset.

7. Park Hyatt Chicago

Downtown Chicago

Tom

HK$5,156 total

includes taxes & fees

1 Nov - 2 Nov

A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.

8. The Ritz-Carlton, Chicago

Downtown Chicago

Fred

HK$4,719 total

includes taxes & fees

1 Nov - 2 Nov

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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.

River Hotel

75 East Wacker Drive Chicago IL

HK$1,127

HK$1,340 total

25 Oct - 26 Oct

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.

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Frequently asked questions

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

You'll find several pricing options for 5-star hotels in Uptown on Expedia. The amount you pay will depend on when you plan to travel, length of your trip and other factors. Compare all of the available accommodation for your chosen dates and make use of our pricing and other filters to land the ideal luxury stay.

Search for the lowest price per night from HK$1,334

What makes a hotel 5 stars in Uptown?

In Uptown, a hotel must provide a specific number of high-end conveniences to earn 5 stars. These may include on-site gyms, saunas and spas, gourmet restaurants, premium bedding, luxury toiletries and more. What also sets 5-star hotels apart is their guest-focused service. You can expect things like concierge services, nightly turn-down services and in-room massage. Some may also offer extra touches like welcome gifts.

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

Find a luxury stay that includes your lodging, meals, drinks and entertainment in Uptown with our handy filters. Search for hotels with a 5-star rating and click on the "All inclusive" filter. Double-check what's included in the upfront price. This way, you're ready to take advantage of all the perks on offer from the moment you get there.

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Check availability on Uptown 5 Star Hotels