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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 $445 per night from Apr 28 to Apr 29
$445
per night
Apr 28 - Apr 29
Stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the helpful staff and the property condition in our ...
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 $390 per night from Apr 28 to Apr 29
$390
per night
Apr 28 - Apr 29
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the restaurant and the helpful staff in our ...
Trump International Hotel & Tower Chicago
Waldorf Astoria Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 16 min walk from Second City
The price is $446 per night from Apr 28 to Apr 29
$446
per night
Apr 28 - Apr 29
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the helpful staff in our reviews. Popular ...
Waldorf Astoria Chicago
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The Langham, Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 4 min drive from Second City
The price is $425 per night from Apr 28 to Apr 29
$425
per night
Apr 28 - Apr 29
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the restaurant and the helpful staff in our ...
The Langham, Chicago
The Peninsula Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 22 min walk from Second City
The price is $475 per night from Apr 28 to Apr 29
$475
per night
Apr 28 - Apr 29
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and a full-service spa. Our guests praise the helpful staff and the property condition ...
The Peninsula Chicago
Nobu Hotel Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 5 min drive from Second City
The price is $409 per night from Apr 28 to Apr 29
$409
per night
Apr 28 - Apr 29
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the restaurant and the helpful staff in our reviews. ...
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 $405 per night from May 26 to May 27
$405
per night
May 26 - May 27
Stay at this spa hotel in Chicago. Enjoy 2 restaurants, a full-service spa, and a fitness center. Popular attractions Michigan Avenue and Chicago Riverwalk are ...
The Ritz-Carlton, Chicago
Park Hyatt Chicago
5 out of 5
Fully refundable
  • 21 min walk from Second City
The price is $455 per night from Apr 26 to Apr 27
$455
per night
Apr 26 - Apr 27
Stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Park Hyatt 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 $605 per night from May 12 to May 13
$605
per night
May 12 - May 13
Stay at this 5-star luxury hotel in Chicago. Enjoy 2 restaurants, a full-service spa, and breakfast. Popular attractions Chicago Riverwalk and Millennium Park ...
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.