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5 Star Hotels in Old Town Chicago

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Tonight Apr 12 - Apr 13Next weekend Apr 18 - Apr 20

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Featured 5 Star Old Town Chicago Hotels

The Langham, Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 4 min drive from Second City
The price is $558 per night from Apr 20 to Apr 21
$558
includes taxes & fees
Apr 20 - Apr 21
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
Four Seasons Hotel Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 18 min walk from Second City
The price is $446 per night from Apr 20 to Apr 21
$446
includes taxes & fees
Apr 20 - Apr 21
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 $392 per night from Apr 20 to Apr 21
$392
includes taxes & fees
Apr 20 - Apr 21
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
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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 $446 per night from Apr 21 to Apr 22
$446
includes taxes & fees
Apr 21 - Apr 22
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 Apr 13 to Apr 14
$558
includes taxes & fees
Apr 13 - Apr 14
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 $484 per night from Apr 13 to Apr 14
$484
includes taxes & fees
Apr 13 - Apr 14
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 $468 per night from Apr 20 to Apr 21
$468
includes taxes & fees
Apr 20 - Apr 21
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 St. Regis Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 4 min drive from Second City
The price is $675 per night from Apr 20 to Apr 21
$675
includes taxes & fees
Apr 20 - Apr 21
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
The Ritz-Carlton, Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 20 min walk from Second City
The price is $427 per night from Apr 20 to Apr 21
$427
includes taxes & fees
Apr 20 - Apr 21
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
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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.