Are there any 5-star vacation rentals in Downtown Chicago?

Although there aren't any 5-star vacation rentals in Downtown Chicago on our site, we have a range of retreats that promise an unforgettable getaway. Discover one that suits your style by checking out our vacation rentals in Downtown Chicago .

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

A busy city street with tall buildings, a bus, and cars.

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Our top choices for Downtown 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

Teresa

NT$23,197 total

includes taxes & fees

Oct 4 - Oct 5

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

2. Trump International Hotel & Tower Chicago

Downtown Chicago

Jorge

NT$19,661 total

includes taxes & fees

Oct 4 - Oct 5

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

3. The Langham, Chicago

Downtown Chicago

Saramae

NT$23,046 total

includes taxes & fees

Oct 25 - Oct 26

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

NT$25,460 total

includes taxes & fees

Oct 4 - Oct 5

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

NT$24,929 total

includes taxes & fees

Oct 25 - Oct 26

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

NT$17,425 total

includes taxes & fees

Oct 25 - Oct 26

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

7. Park Hyatt Chicago

Downtown Chicago

Tom

NT$24,951 total

includes taxes & fees

Sep 27 - Sep 28

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

8. The Ritz-Carlton, Chicago

Downtown Chicago

Fred

NT$18,921 total

includes taxes & fees

Oct 25 - Oct 26

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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 Downtown Chicago.

River Hotel

75 East Wacker Drive Chicago IL

NT$5,137

NT$6,107 total

Sep 27 - Sep 28

includes taxes & fees

8.8/10 Excellent! (5,440 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.

Learn more about Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

See all hotels in Downtown Chicago

A cityscape with tall skyscrapers and a historic tower.

Top Downtown Chicago Hotel Reviews

Frequently asked questions

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

The amount you pay for a 5-star hotel in Downtown Chicago depends on factors like when you plan to travel and the length of your getaway. Our top tip for bagging an awesome deal? Use our pricing filters to check out the available accommodations for your selected dates.

Search for the lowest price per night from NT$6,017

What makes a hotel 5 stars in Downtown Chicago?

In Downtown Chicago, a hotel must offer a certain number of high-end conveniences to earn a 5-star rating. These may include gourmet restaurants, saunas and spas, on-site gyms, complimentary luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their exceptional service. You can look forward to things like nightly turn-down services, in-room massages and concierge services. Some may even offer thoughtful touches such as a welcome gift.

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

Our handy filters are the easiest way to find exactly what you want. Check the "All inclusive" and "5-star" boxes to see the most upscale resorts in Downtown Chicago where your meals, lodging, entertainment and activities are included in the price. At these stays, your trip is pure extravagance from the moment you pull up to the entrance.

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