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Old Town Chicago 5 Stars Hotels

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Check availability on Old Town Chicago 5 Star Hotels

This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

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, (1,004 reviews)
"Liked the layout of our suite and that the hotel was right inside the shopping Mall & Bloomingdales."
United States
August
The price is NT$17,690
NT$21,031 total
includes taxes & fees
Sep 7 - Sep 8
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, (1,985 reviews)
"It was a great place to stay"
United States
Jorge
The price is NT$16,136
NT$19,184 total
includes taxes & fees
Sep 1 - Sep 2
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, (1,019 reviews)
"This place is a true 5 star hotel no question!"
United States
Michael
The price is NT$19,924
NT$23,689 total
includes taxes & fees
Sep 7 - Sep 8
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, (1,013 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$19,921
NT$23,684 total
includes taxes & fees
Aug 30 - Aug 31
The Peninsula Chicago
Exterior

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,006 reviews)
"Beautiful property and excellent service from all staff."
United States
Jim
The price is NT$18,287
NT$21,742 total
includes taxes & fees
Sep 7 - Sep 8
Waldorf Astoria Chicago
Cafe

6. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,001 reviews)
"Great hotel only complaint is on day of check in I sat in lobby and waited 6 hours."
United States
Eric
The price is NT$18,964
NT$22,547 total
includes taxes & fees
Aug 30 - Aug 31
The Ritz-Carlton, Chicago
Indoor pool

7. Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (918 reviews)
"incredible staff and stay here. The team here crushed it and the rooms were fantastic"
Canada
Jordan
The price is NT$12,974
NT$16,221 total
includes taxes & fees
Aug 30 - Aug 31
Nobu Hotel Chicago
Restaurant

8. Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,000 reviews)
"Our room was wonderful"
United States
Jennifer
The price is NT$17,642
NT$20,974 total
includes taxes & fees
Aug 30 - Aug 31
Park Hyatt Chicago
Restaurant

9. The St. Regis Chicago

The St. Regis Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (129 reviews)
"We had a great stay and will come back again in the near future!"
United States
Princess
The price is NT$20,526
NT$24,404 total
includes taxes & fees
Sep 21 - Sep 22
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
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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.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
The price is NT$7,792 per night from Sep 18 to Sep 19
NT$7,792
NT$9,147 total
Sep 18 - Sep 19
includes taxes & fees
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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$5,077

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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