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5 Star Hotels in Old Town Chicago

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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
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 ...
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Opens in a new windowThe Langham, Chicago
Trump International Hotel & Tower Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 4 min drive from Second City
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 ...
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Opens in a new windowTrump 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
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 ...
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Opens in a new windowFour Seasons Hotel Chicago
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The Peninsula Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 22 min walk from Second City
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 ...
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Opens in a new windowThe Peninsula Chicago
Waldorf Astoria Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 16 min walk from Second City
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. ...
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Opens in a new windowWaldorf Astoria Chicago
Nobu Hotel Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 5 min drive from Second City
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 ...
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Opens in a new windowNobu Hotel Chicago
Park Hyatt Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 21 min walk from Second City
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. ...
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Opens in a new windowPark Hyatt Chicago
The Ritz-Carlton, Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 20 min walk from Second City
Stay at this 5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
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Opens in a new windowThe Ritz-Carlton, Chicago
The St. Regis Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 4 min drive from Second City
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. ...
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Opens in a new windowThe St. Regis Chicago
Art Villa
5 out of 5
  • 4 min drive from Second City
Stay at this 5-star luxury aparthotel in Chicago. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions United Center and Chicago Riverwalk ...
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Opens in a new windowArt Villa
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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.