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

Old Town Chicago Hotel Guide - 5 Stars Hotels in Old Town Chicago, Chicago

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Check availability on Old Town Chicago 5 Star Hotels

This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Old Town Chicago 5-star hotels

A person sitting by a window with a view of a cityscape, including a tall tower.

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,001 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 Rp9.483.820
Rp11.275.314 total
includes taxes & fees
1 Nov - 2 Nov
Four Seasons Hotel Chicago
A cityscape with a river, a bridge, and a dining area with tables and chairs.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (2,034 reviews)
"beautiful property in a great location highly recommend staying here this will be our go to spot when visiting chicago"
United States
Mark
The price is Rp8.253.608
Rp9.812.712 total
includes taxes & fees
1 Nov - 2 Nov
Trump International Hotel & Tower Chicago
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.

3. The Langham, Chicago

The Langham, Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,014 reviews)
"Enjoyed my stay, lovely staff and great location"
United States
Saramae
The price is Rp10.199.580
Rp12.126.280 total
includes taxes & fees
25 Oct - 26 Oct
The Langham, Chicago
A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.

4. The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,016 reviews)
"This place was everything!! The location, comfort, food and the stamp was top tier!!!"
United States
Levi
The price is Rp11.183.750
Rp13.296.362 total
includes taxes & fees
1 Nov - 2 Nov
The Peninsula Chicago
A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,001 reviews)
"Great hotel"
United States
Luis
The price is Rp9.896.992
Rp11.766.533 total
includes taxes & fees
1 Nov - 2 Nov
Waldorf Astoria Chicago
A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.

6. Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (940 reviews)
"Great location Helpful staff"
United States
Abhay
The price is Rp7.901.234
Rp9.843.301 total
includes taxes & fees
25 Oct - 26 Oct
Nobu Hotel Chicago
A couple dining at a table with a view of a cityscape and a sunset.

7. Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,000 reviews)
"Nice clean hotel in a great location."
United States
Tom
The price is Rp9.823.806
Rp11.679.522 total
includes taxes & fees
1 Nov - 2 Nov
Park Hyatt Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.

8. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,000 reviews)
"Staff was excellent."
United States
Fred
The price is Rp8.517.544
Rp10.126.510 total
includes taxes & fees
1 Nov - 2 Nov
The Ritz-Carlton, Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.

9. The St. Regis Chicago

The St. Regis Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (132 reviews)
"The location is great. Lovely hotel with great staff."
United States
Xiomara
The price is Rp11.201.644
Rp13.317.633 total
includes taxes & fees
29 Oct - 30 Oct
The St. Regis Chicago
A rooftop lounge with a city skyline view, featuring a sofa set with patterned cushions and a table with drinks and snacks.

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.
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
The price is Rp2.988.298 per night from 1 Nov to 2 Nov
Rp2.988.298
Rp3.552.787 total
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (5,455 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 Rp3.041.567

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.