Popular Illinois Vacation Cities

What to Know

If you’ve never visited Chicago, you may think the "Hub of the Midwest" is just a friendly Midwestern town known for its deep-dish pizzas and "Da Bears", but this city is that and so much more. Located on scenic Lake Michigan, Chi-town’s world-class museums, incredible modern architecture and trendy shopping and dining scenes are sure to impress any visitor.

While the city itself has many must-see attractions downtown, most Chicagoans live and play outside of the central business district If you want to really soak up the local culture, venture to the outlying neighborhoods like Little Italy, Chinatown, Andersonville and Devon Avenue to see traces of immigrant groups and sample their cultures and cuisines. Other popular neighborhoods include the swanky Gold Coast, the raucous Wrigleyville (home of Wrigley Field), Old Town (site of the some of the city's oldest homes) and trendy Bucktown/Wicker Park (filled with boutiques and popular restaurants). Thanks to the city's massive public transit system, every part of Chicago is much closer than you may think.

From upscale dining spots like the posh Alinea to the dives known for Polish sausage like Jim’s Original, foodies will be in hog heaven. Visitors should not leave town without sampling the gooey Chicago deep-dish pizza at Gino’s East, a classic Chicago hot dog (topped with onions, green relish, yellow mustard, pickle spears, fresh tomato and celery salt) at Gold Coast Dogs and a classic Chicago-style Italian beef sandwich at Mr. Beef.

Where to Go

Start with the famous downtown attractions. The heart of the downtown area is called The Loop, named for the circuitous route that the elevated trains make through the business district. The Loop is most active during the business week when downtown workers are out and about, but at night and on weekends, the surge of energy subsides. For scenic views of Chicago’s stunning skyline, check out the Sears Tower Skydeck; ascend to the 103rd-floor observatory where you can see to Michigan, Wisconsin and Indiana on clear days. Or head to the John Hancock Center’s Signature Lounge, a sky-high full bar which also boasts impressive panoramic views of the lake and surrounding skyline. For some fresh air, head to Millennium Park, where you can admire architect Frank Gehry's signature ribbons of steel above the Pritzker Music Pavilion. Shopping is on every tourist’s agenda, and there’s no better place than the legendary Magnificent Mile lined with swanky shops and department stores on Michigan Avenue.

During the warmer months, take one of the many tours offered by the Chicago Architecture Foundation: There are several options available, including walking and bicycle tours and the very popular Chicago architecture river cruise.

Chicago’s cultural scene is vibrant, from the renowned Art Institute of Chicago (featuring Asian, African, Amerindian and American art, European decorative pieces and photography) to many lower-budget independent theater companies. Top draws include the Chicago Symphony Orchestra, the Lyric Opera, the Steppenwolf Theatre Company and the city's gallery scene in the River North neighborhood.

What sets Chicago’s nightlife scene apart from most other big cities is its lack of pretension. While there are plenty of trendy spots (check out the uber-hip Reserve or Rockit Bar), most locals still think the neighborhood pub is where it’s at (try Duffy’s Tavern or Jack Sullivan’s in Lincoln Park). Chicago is a legendary blues town, and tourists shouldn’t miss the North Side clubs, like Kingston Mines, or South Side venues, like the Checkerboard or Lee's Unleaded Blues, where legends like Muddy Waters and Buddy Guy first honed their talent. Need your funny bone ticked? Chicago is also the home of Second City, the country's best-known improv comedy troupe.

When to Go

According to the locals, the only thing that’s certain about the weather is that you can’t predict it-you might encounter the odd 60-degree day in January or February and sometimes August temps drop down to the 50s. In general, however, winters range from cool to bitter cold and late summer is usually oppressively hot and humid. The most pleasant weather tends to occur in the spring and fall.

Chicago is a city of many festivals so keep the following dates in mind when planning your trip. In March is the city’s St. Patrick’s Day celebration, when the Chicago River is dyed green for the occasion. Summer brings the Chicago Blues Festival in June, the Taste of Chicago dishes out tons of fabulous food in July and jet engines roar overhead during the Air & Water Show in August.