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AWWT Chicago City Breaks Chicago USA Route 66 self drive

Chicago City Breaks

A big city with a small town heart is the best way to describe Chicago, the capital of America Mid-West and gateway to Route 66.

"The Windy City" as it is known boasts one the worlds spectacular skylines. The 108 story Willis Tower is the most impressive of the skyscrapers that loom over the downtown region, making a visit to its sky deck a must see. Step out onto the glass ledge here and on a good day you will be able to marvel at a view that spans four states! 

Sat on Lake Michigan, Chicago has 29 miles of lakeshore frontage which are perfect for walking, cycling or simply enjoying the skyline views. In summertime its sandy beaches will be full of beachgoers.

Music is a big part of life here, with the Chicago Symphony Orchestra, the star studded performances of the Lyric Opera of Chicago and the massive jazz and blues scene keeping tourists and locals entertained alike.

The city is a shoppers paradise. The centrally located and elegant Michigan Avenue; is known locally as  the Magnificent Mile. It houses some 240 stores including household names such as Bloomingdales and Tiffany.

Some of our favourite hotels in Chicago

The Pensinsula: Combining the high class service you would expect of the Pensinsula Brand with the friendliest of Mid-West welcomes, the Pensinsula is a the most luxurious of Chicago hotels.

Sheraton Grand Chicago: Just off the Magnificent Mile, this riverfront hotel offers its guests spectacular views of the Chicago River and Lake Michigan.

Millenium Knickerbocker Hotel: Luxurious and stylish, this is perfectly positioned for a Chicago city break. Its within easy walking distance of the cities top musuems and galleries including the Chicago Musuem of Contemporary Art.

Doubletree by Hilton, Magnificent Mile: A great value option in the centre of downtown. The hotels rooftop pool is a popular spot to cool off in the hot summer months.  

Silversmith Hotel: Exuding the style and elegance of the prohibiton era this boutique hotel features a spectacular marble and cast iron grand starircase and marble mosaics. It's not just style over substance though, this hotel is also blessed with a fantastic location. 

For further recommendations or a full quotation for a Chicago city break or other tailor-made holiday please email This email address is being protected from spambots. You need JavaScript enabled to view it. or telephone (01892) 779900

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