Chicago

Chicago Travel Guide

Credit :

Jonny Valiant

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

RECOMMENDED LINKS

Articles about Chicago

When seasoned travelers are told that a hotel promises an “authentic” experience, the visceral response is an eye roll. Authenticity is a vibe, not an adjective that can be blithely assigned to a space. But this type of emotional nirvana—the warm ...
When seasoned travelers are told that a hotel promises an “authentic” experience, the visceral response is an eye roll. Authenticity is a vibe, not an adjective that can be blithely assigned to a space. But this type of emotional nirvana—the warm ...
On her first visit to China earlier this year, chef Stephanie Izard returned with a newfound appreciation for hand-pulled noodles, homemade dumplings, and more. The trip was a fact- and food-finding mission for her newest restaurant, Duck Duck Goa...
On her first visit to China earlier this year, chef Stephanie Izard returned with a newfound appreciation for hand-pulled noodles, homemade dumplings, and more. The trip was a fact- and food-finding mission for her newest restaurant, Duck Duck Goa...
In every great city, there is a flea market that attracts the locals like bees to a strawberry rhubarb pie. In Chicago, it’s Randolph Street Market, a Brooklyn-meets-Paris-style outdoor emporium that pops up once a month during the summer. Get rea...
David Burke’s Primehouse at The James Chicago is known for massive steaks and classic, gut-expanding sides. But every summer, the restaurant veers from its meat-and-potato repertoire with its beloved weekly Ice Cream Pop-Up. Kicking off today a...
In this landscape of hyper esoteric menus, it’s refreshing to break bread—or ham-hock hush puppies—al fresco in the company of high flavor and low pretension. The Logan Square hot spot Parsons Chicken & Fish is a beacon for anyone with a penchant ...
Windy City winters are abysmal. The light at the end of the sub-zero tunnel for long-suffering Chicagoans? A summertime escape; an opportunity to spend hours perched upon sun drenched rooftop decks drinking in the city and, of course, its killer c...
Her father may be fashion royalty, but Dylan Lauren’s achievements in the sweets sector have cemented her status as America’s confectionary queen. With her latest branch of Dylan’s Candy Bar now open on Chicago’s Magnificent Mile, she has big plan...
The Windy City is widely considered the birthplace of the modern skyscraper, so perhaps it’s no surprise that Chicago will soon welcome the country’s first-ever architecture biennial—and also the biggest architecture show ever put on in North Amer...