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5 Star Hotels in Old Town Chicago

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Featured 5 Star Old Town Chicago Hotels

Four Seasons Hotel Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 18 min walk from Second City
The price is $458 per night from Mar 2 to Mar 3
$458
includes taxes & fees
Mar 2 - Mar 3
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
Four Seasons Hotel Chicago
Trump International Hotel & Tower Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 4 min drive from Second City
The price is $374 per night from Feb 9 to Feb 10
$374
includes taxes & fees
Feb 9 - Feb 10
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Trump International Hotel & Tower Chicago
The Langham, Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 4 min drive from Second City
The price is $465 per night from Feb 23 to Feb 24
$465
includes taxes & fees
Feb 23 - Feb 24
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
The Langham, Chicago
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Waldorf Astoria Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 16 min walk from Second City
The price is $449 per night from Feb 19 to Feb 20
$449
includes taxes & fees
Feb 19 - Feb 20
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Waldorf Astoria Chicago
The Peninsula Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 22 min walk from Second City
The price is $558 per night from Feb 3 to Feb 4
$558
includes taxes & fees
Feb 3 - Feb 4
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition ...
The Peninsula Chicago
Park Hyatt Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 21 min walk from Second City
The price is $444 per night from Feb 6 to Feb 7
$444
includes taxes & fees
Feb 6 - Feb 7
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Park Hyatt Chicago
Nobu Hotel Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 5 min drive from Second City
The price is $405 per night from Feb 9 to Feb 10
$405
includes taxes & fees
Feb 9 - Feb 10
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
Nobu Hotel Chicago
The Ritz-Carlton, Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 20 min walk from Second City
The price is $414 per night from Feb 9 to Feb 10
$414
includes taxes & fees
Feb 9 - Feb 10
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
The Ritz-Carlton, Chicago
The St. Regis Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 4 min drive from Second City
The price is $524 per night from Feb 23 to Feb 24
$524
includes taxes & fees
Feb 23 - Feb 24
Stay at this 5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
The St. Regis Chicago
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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.