Explore top 2025 5 Star Hotels in Old Town Chicago
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Top Old Town Chicago 5 Star hotels
Four Seasons Hotel Chicago
120 East Delaware Place Chicago IL
Fully refundableReserve now, pay when you stay
$420 nightly
The price is $493 total per night from Dec 7 to Dec 8
$493 total
Dec 7 - Dec 8
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business ...
9.4/10 Exceptional! (999 reviews)
staff very professional
Reviewed on Nov 9, 2025
The Langham, Chicago
330 North Wabash Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$457 nightly
The price is $536 total per night from Dec 15 to Dec 16
$536 total
Dec 15 - Dec 16
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, ...
9.6/10 Exceptional! (1,003 reviews)
Spa ,pool are awesome
Reviewed on Nov 16, 2025
The Peninsula Chicago
108 East Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$486 nightly
The price is $571 total per night from Dec 9 to Dec 10
$571 total
Dec 9 - Dec 10
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and babysitting. ...
9.6/10 Exceptional! (1,006 reviews)
We love staying at the Peninsula in Chicago. The hotel is clean, the staff is exceptional and the food is delicious. They pay attention to every detail and ensure that you are enjoying your stay. We will definitely keep returning to this hotel when we’re in Chicago!
Reviewed on Nov 19, 2025
Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$394 nightly
The price is $462 total per night from Dec 7 to Dec 8
$462 total
Dec 7 - Dec 8
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly ...
9.4/10 Exceptional! (1,772 reviews)
It was absolutely wonderful. We were upgraded to a suite which was pretty sweet (no pun intended)! At night the surrounding view of the lake along the lakeside of the hotel was spectacular. The Rebar on the mezzanine floor with a live musician playing a saxophone on a Saturday, was a cozy and lively ...
Reviewed on Nov 14, 2025
Waldorf Astoria Chicago
11 E. Walton Street Chicago IL
Fully refundableReserve now, pay when you stay
$406 nightly
The price is $476 total per night from Dec 14 to Dec 15
$476 total
Dec 14 - Dec 15
Total with taxes and fees
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi ...
9.2/10 Wonderful! (1,000 reviews)
Beautiful place and service
Reviewed on Oct 29, 2025
Park Hyatt Chicago
800 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$465 nightly
The price is $546 total per night from Dec 7 to Dec 8
$546 total
Dec 7 - Dec 8
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, ...
9.4/10 Exceptional! (1,001 reviews)
Room was beautiful, large, clean, well equipped. Staff was super friendly and helpful. I wish I could have stayed longer to enjoy the spa and restaurants. Would stay again.
Reviewed on Nov 18, 2025
Nobu Hotel Chicago
155 N. Peoria Street Chicago IL
Fully refundableReserve now, pay when you stay
$327 nightly
The price is $384 total per night from Nov 23 to Nov 24
$384 total
Nov 23 - Nov 24
Total with taxes and fees
This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. There's a bar/lounge on site, and a 24-hour ...
9.2/10 Wonderful! (749 reviews)
Nice room, professional staff, nice welcome, perfect location
Reviewed on Nov 9, 2025
The Ritz-Carlton, Chicago
160 E Pearson Street Chicago IL
Fully refundableReserve now, pay when you stay
$386 nightly
The price is $453 total per night from Dec 21 to Dec 22
$453 total
Dec 21 - Dec 22
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, ...
9/10 Wonderful! (1,001 reviews)
Great breakfast a la carte menu, perfect bar setting, room was spotless, and service in accordance to the Ritz Brand.
Reviewed on Nov 14, 2025
The St. Regis Chicago
401 East Upper Wacker Drive Chicago IL
$446 nightly
The price is $524 total per night from Dec 14 to Dec 15
$524 total
Dec 14 - Dec 15
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public ...
9/10 Wonderful! (79 reviews)
Room was wonderful
Reviewed on Nov 6, 2025
Art Villa
467 N Armour St Chicago IL
$645 nightly
The price is $802 total per night from Nov 30 to Dec 1
$802 total
Nov 30 - Dec 1
Total with taxes and fees
A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. ...
10/10 Exceptional! (2 reviews)
Reviewed on Aug 12, 2025
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Recent Old Town Chicago hotel reviews by fellow wanderers
Congress Plaza Hotel
5 out of 5
Posted 14 hours ago
Travelocity Verified Review
"Lovely room, walkable or bus / drive to attractions. "
A verified traveler stayed at Congress Plaza Hotel
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