5 Stars Hotels in East Side, Chicago from CA $503

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Check prices for these dates

Tonight
Nov 9 - Nov 10
Tomorrow
Nov 10 - Nov 11
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

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, (1,003 reviews)
"Great place to stay in Chicago!"
United States
ryan
The price is CA $706
CA $840 total
includes taxes & fees
Dec 6 - Dec 7
Four Seasons Hotel Chicago
A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (2,081 reviews)
"Amazing property and hospitality!"
United States
Matthew
The price is CA $652
CA $775 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, (1,009 reviews)
"Always an incredible hotel! Definitely one of the best in the USA"
United States
Vincent Haley
The price is CA $848
CA $1,008 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, (1,007 reviews)
"Attentive staff and beautiful spa, pool and rooms."
United States
Courtney
The price is CA $737
CA $877 total
includes taxes & fees
Dec 6 - Dec 7
The Langham, Chicago
A modern living room with a sofa, coffee table, and chairs, a kitchen area with wooden cabinets, and a dining area with a table and chairs.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,004 reviews)
"Very clean and upscale property. Lovely amenities. Great location and staff very friendly."
United States
Loai
The price is CA $630
CA $750 total
includes taxes & fees
Dec 6 - Dec 7
Waldorf Astoria Chicago
A rooftop lounge with outdoor seating, a fire pit, and a large reflective sculpture.

6. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,001 reviews)
"Very helpful staff good for families"
United States
Krikour
The price is CA $652
CA $775 total
includes taxes & fees
Dec 8 - Dec 9
The Ritz-Carlton, Chicago
Room

7. Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (966 reviews)
"The wellness center was my favorite!"
United States
Mauro
The price is CA $503
CA $634 total
includes taxes & fees
Nov 22 - Nov 23
Nobu Hotel Chicago
A modern living room with a sofa, chairs, a coffee table, and a TV. A large window offers a view of a cityscape and a tower.

8. Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,003 reviews)
"Nice clean hotel in a great location."
United States
Tom
The price is CA $618
CA $735 total
includes taxes & fees
Nov 22 - Nov 23
Park Hyatt Chicago
A modern hotel lobby with a large seating area, a view of the city, and a green accent wall.

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 CA $783
CA $931 total
includes taxes & fees
Nov 23 - Nov 24
The St. Regis Chicago
A rooftop dining area with checkered tablecloths, red and blue plates, and a city skyline in the background.

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 high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
Downtown Chicago

10/10 Excellent

This property is perfect. Truly a 5 star experience.
Canada
James
Reviewed October 21, 2026
Trump International Hotel & Tower Chicago

Find out more about East Side

Five Star Hotels in East Side

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 East Side 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 East Side and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in East Side

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 East Side

The results are in, and East Side 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 East Side! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in East Side 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 East Side?

There are a range of pricing options for a 5-star hotel in East Side on Expedia. How much you'll pay will depend on when you want to travel, trip length and other factors. Compare all of the available properties for your preferred dates and make use of our pricing and other filters to land the perfect high-end stay.

  • Search for the lowest price per night from CA $503

What makes a hotel 5 stars in East Side?

Flawless guest service is the hallmark of every 5-star hotel in East Side. From the moment you enter the lobby, staff are at your beck and call, whether arranging customized tours or providing a nightly turn-down service. What's more, hotels have to feature superior conveniences to be considered for a 5-star rating. These can include luxury toiletries, saunas or spas, pools, gastronomic restaurants and knowledgeable concierge.

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

Our handy filters are the easiest way to search for exactly what you're looking for. Check the "All inclusive" and "5-star" boxes to see the most upscale resorts in East Side where your meals, room, activities and entertainment are included in the price. At these stays, your vacation is absolute indulgence from the moment you check in.

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