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Chicago Vacations & Travel Tips

When to Go

Hold onto your hat. The Windy City is probably at its best in the fall. However, summer also sizzles with a great lineup of events and festivals including Lollapalooza. The breezes off the lake make it all worthwhile. Spring is also lovely. Winter sees frigid temperatures, with the wind chill making it feel even colder; if you have a mind to brave the cold, the city transforms into a wonderland around the holidays. 

Region: USA

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Featured Chicago Hotel

  • The Drake Hotel

    The Drake Hotel

    AAA Four Diamond Hotel
    Magnificent Mile, Chicago, IL
    Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.
    • No Golf on Property
      No Golf on Property
    • No Spa Services
      No Spa Services
    • Family Program Not Offered
      Family Program Not Offered
    • Breakfast Not Included
      Breakfast Not Included
    • Not A Beachfront Property
      Not A Beachfront Property
    • Pets Allowed
      Pets Allowed
    • Non-Smoking Property
      Non-Smoking Property
    • Gym/Fitness Center
      Gym/Fitness Center
    • Charge for Wi-Fi
      Charge for Wi-Fi
    • Air Conditioning
      Air Conditioning

    This acclaimed hotel is an elegant symbol near Oak Street Beach at the onset of Chicago's Magnificent Mile, affording guests easy access to the city's most exclusive shopping, nightlife and dining.

    • No Golf on Property
      No Golf on Property
    • No Spa Services
      No Spa Services
    • Family Program Not Offered
      Family Program Not Offered
    • Breakfast Not Included
      Breakfast Not Included
    • Not A Beachfront Property
      Not A Beachfront Property
    • Pets Allowed
      Pets Allowed
    • Non-Smoking Property
      Non-Smoking Property
    • Gym/Fitness Center
      Gym/Fitness Center
    • Charge for Wi-Fi
      Charge for Wi-Fi
    • Air Conditioning
      Air Conditioning

    This acclaimed hotel is an elegant symbol near Oak Street Beach at the onset of Chicago's Magnificent Mile, affording guests easy access to the city's most exclusive shopping, nightlife and dining.

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Fast Facts

The renowned Second City improvisational group got its start in December 1959 and has since grown to become one of the world’s favorite comedy clubs, theatres, and improv schools. Some of the legendary stars who first shined their comedic lights here include Bill Murray, Mike Myers, Joan Rivers, Dan Aykroyd, James Belushi, John Belushi, John Candy, Steve Carell, Tina Fey, and a host of others.

The Willis Tower, formerly known as the Sears Tower, is one of the tallest buildings in the Western Hemisphere. Its 360-degree views span fifty miles and four states.

Chicago’s many nicknames include The Windy City, Chi-town, the City of Big Shoulders, the Second City, and The City That Works.

There are more than 200 theaters, 200 art galleries, and 7,300 restaurants in this cultural mecca.

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