A street with outdoor seating, brick buildings, and signs for a barbershop and a restaurant.

Old Town Chicago 5 Stars Hotels

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Old Town Chicago 5 Star Hotels

Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4

Our top choices for Old Town Chicago 5-star hotels

Suite, 2 Bedrooms, Terrace (Lakeshore) | Lake view

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,000 reviews)
"The staff was so kind and helpful. Great location and dining options. The room was spotless and comfortable"
United States
Teresa
The price is NT$20,049
NT$23,836 total
includes taxes & fees
Oct 4 - Oct 5
Four Seasons Hotel Chicago
Terrace/patio

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (2,019 reviews)
"It was a great place to stay"
United States
Jorge
The price is NT$16,588
NT$19,722 total
includes taxes & fees
Oct 4 - Oct 5
Trump International Hotel & Tower Chicago
Lobby

3. The Langham, Chicago

The Langham, Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,002 reviews)
"Enjoyed my stay, lovely staff and great location"
United States
Saramae
The price is NT$20,826
NT$24,760 total
includes taxes & fees
Oct 4 - Oct 5
The Langham, Chicago
Front of property - evening/night

4. The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,004 reviews)
"First time staying at this Property and we absolutely loved it! Will definitely go back and recommend"
United States
Angela
The price is NT$21,528
NT$25,594 total
includes taxes & fees
Oct 4 - Oct 5
The Peninsula Chicago
Exterior

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,001 reviews)
"Very nice hotel With beautiful rooms"
United States
Victoria
The price is NT$22,993
NT$27,336 total
includes taxes & fees
Oct 1 - Oct 2
Waldorf Astoria Chicago
Indoor pool, open 6:00 AM to 9:00 PM, sun loungers

6. Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (933 reviews)
"Great location Helpful staff"
United States
Abhay
The price is NT$15,529
NT$19,258 total
includes taxes & fees
Sep 20 - Sep 21
Nobu Hotel Chicago
Cafe

7. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,002 reviews)
"Staff was excellent."
United States
Fred
The price is NT$20,240
NT$24,063 total
includes taxes & fees
Oct 18 - Oct 19
The Ritz-Carlton, Chicago
Breakfast, lunch, dinner and brunch served

8. Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,001 reviews)
"Top notch hotel, we were only there for a night but it likely ruined staying at any other hotel now, it was a great experience."
United States
Catherine
The price is NT$21,481
NT$25,539 total
includes taxes & fees
Oct 18 - Oct 19
Park Hyatt Chicago
2 restaurants; breakfast, lunch, dinner, and brunch served

9. The St. Regis Chicago

The St. Regis Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (131 reviews)
"The location is great. Lovely hotel with great staff."
United States
Xiomara
The price is NT$21,354
NT$25,388 total
includes taxes & fees
Oct 4 - Oct 5
The St. Regis Chicago
Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio

10. Art Villa

Art Villa
5.0 star property
West Town
10.0 out of 10, Exceptional, (2 reviews)
Art Villa
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Old Town Chicago.
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
The price is NT$4,836 per night from Sep 30 to Oct 1
NT$4,836
NT$5,750 total
Sep 30 - Oct 1
includes taxes & fees
Still don't see what you're looking for?
See all properties in Old Town Chicago.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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.

Top Old Town Chicago Hotel Reviews

Frequently asked questions

What are the best 5-star hotels in Old Town Chicago?
Waldorf Astoria Chicago is one of the leading picks around the North Side neighborhood of Old Town Chicago based on reviews by Expedia customers. Four Seasons Hotel Chicago and Park Hyatt Chicago are other 5-star hotels in this area that rate highly with travelers.
How much does it cost to stay in a 5-star hotel in Old Town Chicago?
How much you pay for a 5-star hotel in Old Town Chicago can vary depending on when you decide to travel and how long you plan to stay, among other factors. Use our price per night filter and other search tools to land the best rate on a luxurious stay.

  • Search for the lowest price per night from NT$5,750

What makes a hotel 5 stars in Old Town Chicago?
In Old Town Chicago, a hotel needs to provide a specific amount of high-end amenities to earn a 5-star rating. These can include on-site gyms, spas and saunas, gourmet restaurants, luxury bathroom products, premium bedding and more. What also sets 5-star hotels apart is their extraordinary service. You can expect things like nightly turn-down services, concierge services and in-room massages. Some may even offer thoughtful touches like welcome gifts.

Explore a world of travel with Expedia