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Chicago City Breaks
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City Breaks in Chicago

Although sometimes dubbed 'the Second City', Chicago is anything but. The soaring skyscrapers and shops along Michigan Avenue stand in stark contrast to the beautiful waterfront that stretches the length of the city.

Experience Cultural Chicago

Brilliant blues, tasty soul food, rich culture and history; Chicago has something for everybody.

The Blues Trail

Discover the music that’s been a part of Chicago’s soul since the 1920s when the great migration brought musicians from the south. City breaks to Chicago wouldn’t be complete without exploring the rich musical heritage found in the city’s vibrant blues clubs and dive bars. Experience top blues performances at Buddy Guy’s Legends. The club is owned by Buddy, who still makes regular appearances here and performs an annual residency in January, so you might be lucky enough to catch the man in action. Take a look at the memorabilia which covers the walls, to piece together the story of the blues. Alternatively, head to B.L.U.E.S. on Chicago’s north-side to hear local legends and up-and-coming artists perform. If you’d like to explore the city on foot, try one of the many walking tours, which guide you to key spots on the blues trail.

Culture vultures

You can easily fill your Chicago city break with cultural activities. The Art Institute Chicago houses over 300,000 pieces to keep you occupied. See famous works of art including American Gothic by Grant Wood, Edward Hopper’s Nighthawks and The Old Guitarist by Picasso. Curious minds will enjoy the interactive nature of the Museum of Science and Technology. Highlights include an exhibition which delves into the science behind storms; and You! The Experience, which explores what it means to live a healthy life in the 21st century. History buffs can take a trip through billions of years of history at the Field Museum of Natural History and see remains of the world’s largest Tyrannosaurus Rex.

Foodie Adventure

Chicago is a great city break destination for adventurous eaters. You can get an authentic taste of the city by trying these local specialties:  take a bite of a Chicago-style hot dog, grab a slice of deep-dish pizza or savour a famous Italian beef sandwich. The Wicker Park-Bucktown neighbourhood is a foodie paradise with plenty of Mexican and Asian restaurants. And, you can fill up on an eclectic range of American dishes at Feast Restaurant.

Park Life

Millennium Park offers a scenic spot away from the bustle of the city. You can have a picnic in flourishing Lurie Garden, check your reflection in Cloud Gate, see the tribute to Chicagoans at Crown Fountain or watch one of the free concerts here during the spring and summer months. 

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