Chicago

Highlights & Suggested Itineraries

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Forget residents, this place has characters: itinerant artists babbling Beat, Polish aunties stuffing sausage, African-American mothers organizing the block, blue-collar guys bad-mouthing the Bears, a crooner singing the blues on the South Side.

This diverse mix has built a city with an unrivalled tradition of jazz and blues, an astonishing architecture, an appetite for hearty food, award-winning newspapers and some of the most die-hard sports fans you'll ever meet.

Chicago Tours & Activities

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Chicago Blues - A Century in the Making

Blues and jazz musicians have been flocking to Chicago since 1915, so it's no surprise that the city knows how to celebrate its musical heritage with style. The Chicago Blues Festival is a highly regarded three-day festival held in Grant Park on the first weekend in June.

Soon after, Grant Park hosts the weekend-long Chicago Gospel Festival and, on Labor Day weekend, the Chicago Jazz Festival. The German-American Festival is an enjoyable Oktoberfest-type event held in the heart of an old German neighborhood at Lincoln Square during the third weekend in September.