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Find 5 Star Hotels in Old Town Chicago, IL from AED 555

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Check availability on Old Town Chicago 5 Star Hotels

Tonight
28 Aug - 29 Aug
Tomorrow
29 Aug - 30 Aug
This weekend
29 Aug - 31 Aug
Next weekend
5 Sep - 7 Sep

Compare Old Town Chicago 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Our top choices for Old Town Chicago 5-star hotels

Trump International Hotel & Tower Chicago
Bar (on property)

Trump International Hotel & Tower Chicago

5.0 star property
9.4 out of 10, Exceptional, (1696)
"Location, staff and accommodations were excellent. "
The price is AED 1,694
AED 1,989 total
includes taxes & fees
7 Sep - 8 Sep
Trump International Hotel & Tower Chicago
Four Seasons Hotel Chicago
Reception

Four Seasons Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (1001)
"Great location "
The price is AED 1,947
AED 2,285 total
includes taxes & fees
3 Sep - 4 Sep
Four Seasons Hotel Chicago
The Langham, Chicago
Lobby

The Langham, Chicago

5.0 star property
9.8 out of 10, Exceptional, (1003)
"Location can’t be beat. Hotel is excellent! "
The price is AED 2,045
AED 2,401 total
includes taxes & fees
21 Sep - 22 Sep
The Langham, Chicago
The Peninsula Chicago
Front of property - evening/night

The Peninsula Chicago

5.0 star property
9.8 out of 10, Exceptional, (1005)
"Fantastic hotel "
The price is AED 2,296
AED 2,695 total
includes taxes & fees
1 Sep - 2 Sep
The Peninsula Chicago
Waldorf Astoria Chicago
Exterior

Waldorf Astoria Chicago

5.0 star property
9.4 out of 10, Exceptional, (1003)
"Great location "
The price is AED 1,954
AED 2,294 total
includes taxes & fees
21 Sep - 22 Sep
Waldorf Astoria Chicago
Park Hyatt Chicago
Suite, Terrace (Water Tower) | 1 bedroom, premium bedding, down comforters, pillowtop beds

Park Hyatt Chicago

5.0 star property
9.6 out of 10, Exceptional, (1000)
"It's a beautiful and comfortable hotel."
The price is AED 2,259
AED 2,652 total
includes taxes & fees
1 Sep - 2 Sep
Park Hyatt Chicago
Nobu Hotel Chicago
Indoor pool, open 6:00 AM to 9:00 PM, sun loungers

Nobu Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (714)
"Great location, amenities and staff. "
The price is AED 1,245
AED 1,462 total
includes taxes & fees
21 Sep - 22 Sep
Nobu Hotel Chicago
The Ritz-Carlton, Chicago
Bar (on property)

The Ritz-Carlton, Chicago

5.0 star property
9.2 out of 10, Wonderful, (1003)
"Beautiful place "
The price is AED 1,895
AED 2,225 total
includes taxes & fees
28 Sep - 29 Sep
The Ritz-Carlton, Chicago
The St. Regis Chicago
2 restaurants, breakfast served

The St. Regis Chicago

5.0 star property
9.0 out of 10, Wonderful, (73)
"Top tier "
The price is AED 2,398
AED 2,815 total
includes taxes & fees
21 Sep - 22 Sep
The St. Regis Chicago
Art Villa
Hot tub

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is AED 2,755
AED 4,556 total
includes taxes & fees
1 Sep - 2 Sep
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.
The Wade

The Wade

644 N Lake Shore Dr, Chicago, IL
The price is AED 555 per night from Sep 2 to Sep 3
AED 555
AED 651 total
2 Sep - 3 Sep
includes taxes & fees
8.2/10 Very Good! (1,220 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

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Frequently asked questions

What are the best 5-star hotels in Old Town Chicago?
According to reviews by our customers, Waldorf Astoria Chicago is one of the leading retreats for an indulgent stay in the North Side neighborhood of Old Town Chicago. Looking for more 5-star hotels around the area? Four Seasons Hotel Chicago and Park Hyatt Chicago will meet your high-end needs.
How much does it cost to stay in a 5-star hotel in Old Town Chicago?
You can find various pricing options for 5-star hotels in Old Town Chicago on Expedia. How much you'll pay will depend on when you travel, length of stay and other factors. Compare all of the available accommodations for your preferred dates and use our pricing and other filters to score the perfect high-end stay.

  • Search for the lowest price per night from AED 555

What makes a hotel 5 stars in Old Town Chicago?
In Old Town Chicago, a hotel must offer a certain number 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 guest-focused service. You can expect things like concierge services, in-room massages and nightly turn-down services. Some may also offer extra touches such as welcome gifts.