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Chicago Travel Guide

Photo: Jonny Valiant

Photo: Jonny Valiant

Photo: Jonny Valiant

Photo: Marcus Nilsson

Photo: David Nicolas


Comedy, jazz clubs, fine dining and glittery skyscrapers to rival New York’s, plus a Midwestern friendliness that’s all its own – when you travel to Chicago, you’ll be charmed by a wholly unique metropolis. During the 19th century, Chicago was a major hub for the shipping industry; present day Chicago is better known for its vibrant music scene – the city played a seminal role in the emergence of jazz and blues, and its symphony orchestra is second to none – but its history as a major port city is still reflected in Chicago’s vibrant waterfront district. Design and architecture buffs should visit Chicago for some of the country’s most cutting-edge buildings and monuments, like Cloud Gate, the giant reflective bean sculpture found in Millennium Park; sports fans will want to plan a trip to cheer on their favorite team, be it the Cubs, the Bears, the Bulls, the Blackhawks, or the White Sox.

Things Not to Miss in Chicago

• Viewing the Chicago skyline from Millennium Park
 • Visiting the Lincoln Park Zoo
 • Watching a game at Wrigley Field
 • Visiting the Chicago Art Institute
 • Seeing a comedy show at Second City Theater
 • Shopping in downtown Chicago, especially in The Loop
 • Hop on the “L” – the elevated train that connects the different neighborhoods of Chicago

When to Go to Chicago

It’s best to make your Chicago travel plans in the spring or in fall, when temperatures are warm and the city offers plenty of festivals and activities. Peak travel season occurs during the summer months, when the weather is at its warmest – however; the high season means larger crowds and higher prices at hotels. Winters in Chicago can be very chilly – and snowy – but you may want to brave a blizzard or two for the lower airfare and hotel prices.

Don't Miss

  • Watching a Cubs game from the bleachers at Wrigley Field—the second oldest ballpark in the majors

  • Laughing ‘til your sides hurt at Second City, Chicago’s famous home for comedy improv; or, taking in some serious drama at acclaimed Steppenwolf Theatre

  • Catching a glimpse of the historic Windy City skyline—the John Hancock Center, the Sears Tower, and the Wrigley Building—on an architecture river cruise along the Chicago River

Chicago Tips and Advice from Our Local Experts


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