Chicago Holidays

Holidays in Chicago

Chicago will not disappoint your big city expectations – you can spend hours shopping along the Magnificent Mile, Oak Street or the State Street Retail Historic District or for sports fans, support the Chicago Cubs, Bulls or Bears in a game. Don't miss the traditional cuisine of the city with the renowned deep-dish pizza or a Chicago-style hot dog. Along the shores of Lake Michigan you will find bustling Navy Pier, where the attractions will keep you captivated all day.

For evening entertainment, catch a show in the Downtown Theatre District or pick your perfect gourmet restaurant to dine in before tapping your toes along to blues or jazz music emanating from one of the popular bars or clubs.

Admire the distinct urban culture of the ‘Second City’ of the USA by visiting one of Chicago’s many cultural institutions, especially the Museum Campus, which is both scenic and enlightening. Gazing over the impressive landscape of the city on the 103rd floor of Skydeck Chicago in the Willis Tower, or the 94th floor of the Hancock Observatory allows you to take in the beauty of this Illinois city.

The city of Chicago is also a place where you can enjoy the urban landscape combined with wide open spaces, as there are over 7,300 acres of municipal parkland to roam. In the summer you can explore the ‘Taste of Chicago’ event in Grant Park to savour the flavours of the city. Ice skate in the winter in Millennium Park, where you can also view the stainless steel Cloud Gate sculpture. Other exciting outdoor artwork includes the interactive Crown Fountain or the 50 tonne bright red flamingo sculpture. For further exploration, the world-class Art Institute of Chicago showcases an outstanding collection of art work.

Whilst Chicago may have the nickname ‘The Windy City,’ do not be alarmed because the city can be enjoyed at any time of the year. Snowy winters exaggerate the city’s charm, while warm summers make strolling around attractions more pleasurable.

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We Found 7 Hotels
Waldorf Astoria Chicago
  • City Break
USA | Chicago
A stunning and luxurious hotel tucked away, with easy walk access to many of Chicago's attractions including 360 Chicago, formerly John Hancock Observatory.
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Trump International Hotel and Tower
  • City Break
USA | Chicago
A contemporary and luxurious hotel with fantastic dining and a spa, located in downtown Chicago by the river.
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Peninsula Chicago
  • City Break
USA | Chicago
An extremely luxurious and classic hotel located in the Magnificent Mile area, perfect for a central location to shops and restaurants.
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Hotel Monaco Chicago, a Kimpton Hotel
  • City Break
USA | Chicago
Situated in downtown Chicago by the river, Hotel Monaco is a unique setting for a stay in the city.
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Radisson Blu Aqua Hotel
  • City Break
USA | Chicago
Contemporary and modern hotel situated nearby to the Magnificent Mile for shopping.
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Palmer House Hilton
  • City Break
USA | Chicago
Iconic Chicago hotel situated close by to State Street and Michigan Avenue for shopping and well suited to both couples and families.
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The Langham
  • City Break
USA | Chicago
Located within walking distance of Grant Park and the Magnificent Mile, this is a luxurious hotel with a fantastic afternoon tea service.
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Western & Oriental Brochures