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

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Check availability on Old Town Chicago 5 Star Hotels

Tonight
3 Jul - 4 Jul
Tomorrow
4 Jul - 5 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

Top Old Town Chicago 5 Star Hotels

The Peninsula Chicago
Front of property – evening/night

The Peninsula Chicago

5.0 star property
9.8 out of 10, Exceptional, (1001)
"Always love our stay at The Peninsula! "
The price is 16.352.500 ₫
19.196.199 ₫ total
includes taxes & fees
6 Jul - 7 Jul
The Peninsula Chicago
The Langham, Chicago
Lobby

The Langham, Chicago

5.0 star property
9.8 out of 10, Exceptional, (1000)
"I had such a lovely staycation, and I recommend a stay here to everyone I know. "
The price is 14.340.488 ₫
16.834.300 ₫ total
includes taxes & fees
27 Jul - 28 Jul
The Langham, Chicago
Four Seasons Hotel Chicago
Reception

Four Seasons Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (999)
"great hotel and close to all the activite"
The price is 13.997.740 ₫
16.431.947 ₫ total
includes taxes & fees
13 Jul - 14 Jul
Four Seasons Hotel Chicago
Trump International Hotel & Tower Chicago
Terrace/patio

Trump International Hotel & Tower Chicago

5.0 star property
9.4 out of 10, Exceptional, (1627)
"Great hotel with great staff."
The price is 12.264.375 ₫
14.397.003 ₫ total
includes taxes & fees
10 Jul - 11 Jul
Trump International Hotel & Tower Chicago
Waldorf Astoria Chicago
Exterior

Waldorf Astoria Chicago

5.0 star property
9.4 out of 10, Exceptional, (1001)
"The room service and overall staff at this property is excellent "
The price is 13.899.625 ₫
16.316.771 ₫ total
includes taxes & fees
13 Jul - 14 Jul
Waldorf Astoria Chicago
Nobu Hotel Chicago
Indoor pool, open 6:00 AM to 9:00 PM, pool loungers

Nobu Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (684)
"Always a great stay! Staff are amazing and attentive! Will be back. Also great neighborhood for walking and amazing food options. "
The price is 12.431.825 ₫
14.593.719 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Nobu Hotel Chicago
Park Hyatt Chicago
1 bedroom, premium bedding, down duvets, pillow-top beds

Park Hyatt Chicago

5.0 star property
9.6 out of 10, Exceptional, (1001)
"Superb customer service, clean hotel!"
The price is 13.997.740 ₫
16.432.300 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Park Hyatt Chicago
The St. Regis Chicago
Indoor pool

The St. Regis Chicago

5.0 star property
9.0 out of 10, Wonderful, (69)
"Excellent service! Always a great time! "
The price is 15.907.712 ₫
18.674.063 ₫ total
includes taxes & fees
27 Jul - 28 Jul
The St. Regis Chicago
The Ritz-Carlton, Chicago
View from property

The Ritz-Carlton, Chicago

5.0 star property
9.2 out of 10, Wonderful, (1002)
"Best hotel in Chicago "
The price is 12.681.284 ₫
14.886.560 ₫ total
includes taxes & fees
3 Aug - 4 Aug
The Ritz-Carlton, Chicago
Art Villa
Rainfall showerhead, hair dryer, soap, shampoo

Art Villa

5.0 star property
The price is 13.055.836 ₫
22.390.526 ₫ total
includes taxes & fees
10 Jul - 11 Jul
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 4.803.187 ₫ per night from 9 Jul to 10 Jul
4.803.187 ₫
5.638.460 ₫ total
9 Jul - 10 Jul
includes taxes & fees
8.4/10 Very Good! (4,320 reviews)
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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 4.421.716 ₫

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.