Compare and book 5 Star hotels in Old Town Chicago, Chicago

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Check availability on Old Town Chicago 5 Star Hotels

Our top choices for Old Town Chicago 5-star hotels

Reception
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (999)
"Amazing hotel"
United States
David
The price is 11.075.400 ₫
13.001.411 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Four Seasons Hotel Chicago
Lobby
The Langham, Chicago

The Langham, Chicago

The Langham, Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1003)
"Langham is always a superior stay"
United States
THADDEUS LAMONT
The price is 10.897.403 ₫
12.792.462 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Langham, Chicago
Front of property – evening/night
The Peninsula Chicago

The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1004)
"Excellent service throughout the hotel"
United States
Karen
The price is 12.525.750 ₫
14.703.977 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Peninsula Chicago
Bar (on property)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1778)
"Amazing hotel, location, staff, and food!!"
United States
Wendy
The price is 7.291.305 ₫
8.559.263 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Trump International Hotel & Tower Chicago
Exterior
Waldorf Astoria Chicago

Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1000)
"Absolutely fantastic hotel great service, you couldn’t ask for more."
United States
J Michael
The price is 10.653.480 ₫
12.506.120 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Waldorf Astoria Chicago
Suite, Terrace (Water Tower) | Premium bedding, down duvets, pillow-top beds, minibar
Park Hyatt Chicago

Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1001)
"Stay was amazing!!! The staff was so friendly, kind, and thoughtful! The rooms were soooo beyond perfect and lovely! And the food at the restaurant was amazing.. especially breakfast! You won’t regret staying here!!! "
United States
Larissa
The price is 11.470.950 ₫
13.465.748 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Park Hyatt Chicago
Indoor pool, open 6:00 AM to 9:00 PM, pool loungers
Nobu Hotel Chicago

Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (757)
"Great location, amenities and staff. "
United States
Nicholas
The price is 8.405.437 ₫
9.867.143 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Nobu Hotel Chicago
Bar (on property)
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1001)
"Great breakfast a la carte menu, perfect bar setting, room was spotless, and service in accordance to the Ritz Brand."
United States
Alejandro Randolph
The price is 9.770.085 ₫
11.469.103 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
The Ritz-Carlton, Chicago
2 restaurants, breakfast served
The St. Regis Chicago

The St. Regis Chicago

The St. Regis Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (83)
"Nice place "
United States
John
The price is 11.761.020 ₫
13.806.261 ₫ total
includes taxes & fees
24 Dec - 25 Dec
The St. Regis Chicago
Interior
Art Villa

Art Villa

Art Villa
5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
Art Villa
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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 Old Town Chicago.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL
The price is 2.636.200 ₫ per night from 25 Dec to 26 Dec
2.636.200 ₫
3.094.636 ₫ total
25 Dec - 26 Dec
includes taxes & fees
8.4/10 Very Good! (5,354 reviews)
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Top Old Town Chicago Hotel Reviews

Frequently asked questions

What are the best 5-star hotels in Old Town Chicago?
Get the indulgent experience at Waldorf Astoria Chicago, Four Seasons Hotel Chicago and Park Hyatt Chicago. These are some of the 5-star options around the North Side neighbourhood of Old Town Chicago that are rated best by Expedia travellers.
How much does it cost to stay in a 5-star hotel in Old Town Chicago?
The amount you pay for a 5-star hotel in Old Town Chicago can vary according to the time of year you travel and how long you plan to stay, among several factors. Use our price per night filter and other search tools to find the best deal on a high-end getaway.

  • Search for the lowest price per night from 3.094.636 ₫

What makes a hotel 5 stars in Old Town Chicago?
In Old Town Chicago, a hotel must offer a specific amount of top-notch amenities to be rated 5 stars. These may include gourmet restaurants, on-site gyms, saunas and spas, complimentary luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their outstanding service. You can look forward to things like in-room massages, concierge services and nightly turn-down services. Some may even offer extra touches such as welcome gifts.

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