Old Town Chicago 5 Stars Hotels

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Our top choices for Old Town Chicago 5-star hotels

Suite, 2 Bedrooms, Terrace (Lakeshore) | Lake view
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1003)
"Amazing place! Our family of 6 had a fantastic time here for a night. "
United States
Brooke
The price is NT$13,228
NT$15,528 total
includes taxes & fees
Jan 11 - 2026/1/12
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, (1002)
"Langham is always a superior stay"
United States
THADDEUS LAMONT
The price is NT$12,741
NT$14,957 total
includes taxes & fees
Jan 11 - 2026/1/12
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, (1007)
"Excellent service throughout the hotel"
United States
Karen
The price is NT$13,896
NT$16,313 total
includes taxes & fees
Jan 16 - 2026/1/17
The Peninsula Chicago
Terrace/patio
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, (1784)
"Amazing hotel, location, staff, and food!!"
United States
Wendy
The price is NT$9,370
NT$11,000 total
includes taxes & fees
Jan 4 - 2026/1/5
Trump International Hotel & Tower Chicago
Front of property
Waldorf Astoria Chicago

Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1002)
"Absolutely fantastic hotel great service, you couldn’t ask for more."
United States
J Michael
The price is NT$11,968
NT$14,049 total
includes taxes & fees
Jan 11 - 2026/1/12
Waldorf Astoria Chicago
Breakfast, lunch, dinner served; American cuisine, alfresco dining
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 NT$11,598
NT$13,614 total
includes taxes & fees
Jan 7 - 2026/1/8
Park Hyatt Chicago
Indoor pool, open 6:00 AM to 9:00 PM, sun loungers
Nobu Hotel Chicago

Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (760)
"Great location, amenities and staff. "
United States
Nicholas
The price is NT$10,006
NT$11,746 total
includes taxes & fees
Dec 28 - Dec 29
Nobu Hotel Chicago
Cafe
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)
"Festive, staff, food and bar all a perfect 10!"
United States
Angela
The price is NT$11,669
NT$13,698 total
includes taxes & fees
Jan 2 - 2026/1/3
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, (85)
"Nice place "
United States
John
The price is NT$14,047
NT$16,489 total
includes taxes & fees
Jan 1 - 2026/1/2
The St. Regis Chicago
Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio
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 NT$3,086 per night from Jan 6 to Jan 7
NT$3,086
NT$3,623 total
Jan 6 - 2026/1/7
includes taxes & fees
8.4/10 Very Good! (5,394 reviews)
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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$3,623

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.

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