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5 Star Hotels in Old Town Chicago

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Featured 5 Star Old Town Chicago Hotels

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 Jan 2 to Jan 3
$374
includes taxes & fees
Jan 2 - Jan 3, 2025
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
Four Seasons Hotel Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 18 min walk from Second City
The price is $417 per night from Jan 16 to Jan 17
$417
includes taxes & fees
Jan 16 - Jan 17, 2025
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
The Langham, Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 4 min drive from Second City
The price is $411 per night from Jan 6 to Jan 7
$411
includes taxes & fees
Jan 6 - Jan 7, 2025
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 $502 per night from Jan 19 to Jan 20
$502
includes taxes & fees
Jan 19 - Jan 20, 2025
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
Park Hyatt Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 21 min walk from Second City
The price is $424 per night from Jan 23 to Jan 24
$424
includes taxes & fees
Jan 23 - Jan 24, 2025
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
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 Jan 5 to Jan 6
$558
includes taxes & fees
Jan 5 - Jan 6, 2025
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
Nobu Hotel Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 5 min drive from Second City
The price is $417 per night from Jan 12 to Jan 13
$417
includes taxes & fees
Jan 12 - Jan 13, 2025
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 $389 per night from Jan 2 to Jan 3
$389
includes taxes & fees
Jan 2 - Jan 3, 2025
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 $528 per night from Jan 14 to Jan 15
$528
includes taxes & fees
Jan 14 - Jan 15, 2025
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.