East Side 5 Stars Hotels

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Check prices for these dates

Tonight
Nov 6 - Nov 7
Tomorrow
Nov 7 - Nov 8
This weekend
Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

Our top choices for East Side 5-star hotels

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

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,000 reviews)
"Great place to stay in Chicago!"
United States
ryan
The price is NT$16,088
NT$19,127 total
includes taxes & fees
Dec 6 - Dec 7
Four Seasons Hotel Chicago
A cityscape with a river, a bridge, and a dining area with tables and chairs.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (2,077 reviews)
"Amazing property and hospitality!"
United States
Matthew
The price is NT$15,144
NT$18,004 total
includes taxes & fees
Nov 15 - Nov 16
Trump International Hotel & Tower Chicago
A rooftop bar with seating and a view of the city skyline at night.

3. The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,008 reviews)
"Always an incredible hotel! Definitely one of the best in the USA"
United States
Vincent Haley
The price is NT$19,699
NT$23,420 total
includes taxes & fees
Dec 6 - Dec 7
The Peninsula Chicago
A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.

4. The Langham, Chicago

The Langham, Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,004 reviews)
"Attentive staff and beautiful spa, pool and rooms."
United States
Courtney
The price is NT$17,138
NT$20,376 total
includes taxes & fees
Dec 6 - Dec 7
The Langham, Chicago
A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,000 reviews)
"Great hotel"
United States
Luis
The price is NT$14,651
NT$17,419 total
includes taxes & fees
Dec 6 - Dec 7
Waldorf Astoria Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.

6. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,000 reviews)
"Very helpful staff good for families"
United States
Krikour
The price is NT$12,928
NT$15,370 total
includes taxes & fees
Dec 6 - Dec 7
The Ritz-Carlton, Chicago
A modern hotel room with a large window offering a city view, a wooden desk with a laptop, and a small seating area.

7. Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (963 reviews)
"Great location Helpful staff"
United States
Abhay
The price is NT$11,730
NT$14,769 total
includes taxes & fees
Nov 22 - Nov 23
Nobu Hotel Chicago
A couple dining at a table with a view of a cityscape and a sunset.

8. Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,001 reviews)
"Excellent experience. I’d recommend this property for their outstanding service and updated rooms."
United States
Marissa
The price is NT$14,372
NT$17,087 total
includes taxes & fees
Nov 23 - Nov 24
Park Hyatt Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.

9. The St. Regis Chicago

The St. Regis Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (136 reviews)
"Gorgeous and family friendly"
United States
Alise
The price is NT$17,654
NT$20,988 total
includes taxes & fees
Nov 22 - Nov 23
The St. Regis Chicago
A rooftop lounge with a city skyline view, featuring a sofa set with patterned cushions and a table with drinks and snacks.

10. Art Villa

Art Villa
5.0 star property
West Town
10.0 out of 10, Exceptional, (2 reviews)
Art Villa

Top East Side Hotel Reviews

A rooftop bar with seating and a view of the city skyline at night.
The Peninsula Chicago

The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago

10/10 Excellent

Excellent hotel, my only complaint would be the Peninsula food service. We ate at the Shanghai Terrace our first night on site and honestly the food was only 2 stars. Specifically the appetizers were minuscule, and 90% pastry dough. Whatever filling was supposed to be inside all the dough largely wasn’t. The whole Peking duck was arranged haphazardly on the plate, the skin was not really crispy, and the taste experience was completely lackluster. As to the main dining room the service...
United States
Michael
Reviewed September 27, 2025
The Peninsula Chicago

Frequently Asked Questions

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

How much you pay for a 5-star hotel in East Side can vary depending on what time of year you travel and how long you plan to be away, among several factors. Take advantage of our price per night filter and other search tools to land the best rate on a high-end getaway.

  • Search for the lowest price per night from NT$11,730

What makes a hotel 5 stars in East Side?

In East Side, a hotel must offer a specific amount of high-end amenities to be rated 5 stars. These may include on-site gyms, saunas and spas, gourmet restaurants, complimentary luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their guest-centric service. You'll enjoy things like nightly turn-down services, concierge services and in-room massages. Some may also offer additional touches like a welcome gift.

Are there any 5-star all-inclusive resorts in East Side?

Find a luxury stay that includes your room, meals, activities and entertainment in East Side with the help of Expedia's filters. Search for resorts with a 5-star rating and click on the "All inclusive" filter. Be sure to check what's included in the price. This way, you can take full advantage of all the perks on offer from the moment you get there.

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