Photo by trenton.badillo

Old Town Chicago 5 Stars Hotels

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Old Town Chicago 5 Star Hotels

Tonight
Nov 2 - Nov 3
Tomorrow
Nov 3 - Nov 4
Next weekend
Nov 7 - Nov 9
In two weeks
Nov 14 - Nov 16

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

Lobby
The Langham, Chicago
The Langham, Chicago
5.0 star property
9.8 out of 10, Exceptional, (1018)
"Excellent stay"
United States
KEDARNATH
The price is NT$15,377
NT$18,051 total
includes taxes & fees
Nov 23 - Nov 24
The Langham, Chicago
Bar (on property)
Trump International Hotel & Tower Chicago
Trump International Hotel & Tower Chicago
5.0 star property
9.4 out of 10, Exceptional, (1758)
"Very clean very nice hotel. Easy accesss to restaurants and shopping. "
United States
Melvin
The price is NT$13,256
NT$15,561 total
includes taxes & fees
Nov 9 - Nov 10
Trump International Hotel & Tower Chicago
Reception
Four Seasons Hotel Chicago
Four Seasons Hotel Chicago
5.0 star property
9.4 out of 10, Exceptional, (999)
"Amazing hotel"
United States
David
The price is NT$15,062
NT$17,681 total
includes taxes & fees
Nov 24 - Nov 25
Four Seasons Hotel Chicago
Front of property - evening/night
The Peninsula Chicago
The Peninsula Chicago
5.0 star property
9.8 out of 10, Exceptional, (1025)
"Fantastic hotel "
United States
Jennifer
The price is NT$17,674
NT$20,748 total
includes taxes & fees
Nov 16 - Nov 17
The Peninsula Chicago
Exterior
Waldorf Astoria Chicago
Waldorf Astoria Chicago
5.0 star property
9.4 out of 10, Exceptional, (1001)
"This is a very nice hotel. The staff is super accommodating. The location is one of the best in the area for shopping and dining. "
United States
william
The price is NT$14,493
NT$17,013 total
includes taxes & fees
Nov 23 - Nov 24
Waldorf Astoria Chicago
Indoor pool, open 6:00 AM to 9:00 PM, sun loungers
Nobu Hotel Chicago
Nobu Hotel Chicago
5.0 star property
9.4 out of 10, Exceptional, (742)
"Everything was perfect. "
United States
Kaitlyn
The price is NT$10,651
NT$12,503 total
includes taxes & fees
Nov 23 - Nov 24
Nobu Hotel Chicago
Suite, Terrace (Water Tower) | 1 bedroom, premium bedding, down comforters, pillowtop beds
Park Hyatt Chicago
Park Hyatt Chicago
5.0 star property
9.6 out of 10, Exceptional, (1000)
"beautiful room and hotel great bar!"
United States
ravi
The price is NT$15,215
NT$17,862 total
includes taxes & fees
Nov 23 - Nov 24
Park Hyatt Chicago
Bar (on property)
The Ritz-Carlton, Chicago
The Ritz-Carlton, Chicago
5.0 star property
9.2 out of 10, Wonderful, (1001)
"Great location"
United States
Peter
The price is NT$13,648
NT$16,021 total
includes taxes & fees
Nov 9 - Nov 10
The Ritz-Carlton, Chicago
2 restaurants, breakfast served
The St. Regis Chicago
The St. Regis Chicago
5.0 star property
9.2 out of 10, Wonderful, (77)
"Top tier "
United States
Maurice
The price is NT$14,262
NT$16,743 total
includes taxes & fees
Nov 24 - Nov 25
The St. Regis Chicago
Interior
Art Villa
Art Villa
5.0 star property
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
The price is NT$16,568
NT$31,681 total
includes taxes & fees
Nov 5 - Nov 6
Art Villa
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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$3,632 per night from Nov 23 to Nov 24
NT$3,632
NT$4,263 total
Nov 23 - Nov 24
includes taxes & fees
8.4/10 Very Good! (5,180 reviews)
Still don't see what you're looking for?
See all properties in Old Town Chicago.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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$3,645

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.

Explore a world of travel with Expedia