Chicago Travel Guide

A city of neighborhoods, Chicago is wholly unique and no matter where you go, each part has its own draw: the buzzing Loop downtown and upscale River. Read More

A city of neighborhoods, Chicago is wholly unique and no matter where you go, each part has its own draw: the buzzing Loop downtown and upscale River North, artsy Wicker Park, scholarly Hyde Park, and flamboyant Boystown. Add to that some of the world’s best architecture and museums, a thriving music and dining scene, and its multi-cultural make-up, and you’ll see why for many, the Second City is second to none.

Whether you’re in the mood for comedy, jazz clubs, fine dining, glittering skyscrapers, or an afternoon of shopping, T+L’s Chicago travel guide has the scoop on where to go. 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 a standout—but its history as a major port city is still reflected in Chicago’s vibrant waterfront district. Design and architecture buffs should plan a Chicago trip 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 cheer on their favorite team, be it the Cubs, the Bears, the Bulls, the Blackhawks, or the White Sox.

In recent years, the city’s hotel scene has gotten a major boost. While its grand dames like The Drake or Palmer House Hilton are rightfully famous, newcomers like the Thompson Chicago and Virgin Hotel Chicago have both brought a slick, modern vibe. The recently opened Chicago Athletic Association, housed in a Gothic era building with Art Deco interiors, has become a destination itself—especially in the summer, when its rooftop patio is a major draw.

It’s best to visit Chicago 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—though the high season means larger crowds and higher prices at hotels. Winters in Chicago can be chilly and snowy, but you may want to brave a blizzard or two for the lower airfare and hotel prices. When you arrive, the Midwestern friendliness will stay with you no matter what’s happening outside.