Fall in the Windy City

Fall in the Windy City

Put on your walking shoes; it’s time to head to the shore of Lake Michigan and explore the third-largest city in the United States.

Okay, if you’ve never been to Chicago, take a day to see all the usual sights and explore the Loop. Your first stop should be one of the city’s two Visitor Information Centers, which are both interesting destinations in and of themselves. The main Visitor Information Center is located inside the Chicago Cultural Center, a sumptuous Gilded Age building that is now a historic landmark. The Center hosts a variety of free art exhibits and concerts each week.

The other Visitors Center–Macy’s flagship store on State Street—offers its own delights (we’re partial to the Frango mints). The golden age of department stores is on display here, including a stunning 1907 Tiffany glass ceiling and the longest running restaurant in the country, the famed Walnut Room.

Now that you’ve looked around, grabbed a map and bought a GoChicago pass, it’s time to check out Chicago’s world-class museums, many of which are right in or close to downtown. Grab a Chicago-style hot dog and find a bench in Millennium Park to do some people-watching before planning out the rest of your day. A visit to the Field Museum, the Art Institute of Chicago or the Museum of Science and Industry could easily take up a whole day each, so don’t try to visit them all at once.

Like any city, there’s more here than just the tourist hotspots. Chicago is especially proud of its neighborhoods, and shows them off to visitors with the free Chicago Greeter program. You can take advantage of free daily tours of Millennium Park and the Loop departing from the Cultural Center, or you can sign up before you arrive for personalized guided tours of whatever aspect of Chicago that interests you—for free. Visit the gardens of Lincoln Park, or explore the boutiques and art galleries of Wicker Park and Bucktown with your very own tour guide. Cutting through many of these north side neighborhoods is The 606, an elevated green space and trail created from an old train line.

Chicago’s many ethnic neighborhoods are also a popular draw. Little Italy is home to some of the city’s oldest and most impressive churches, like The Shrine of Our Lady of Pompeii, and most delicious food, like that found at the Maxwell Street Market. Less well known is Chicago’s Little India, a ten-block stretch of Devon Avenue on the city’s north side where sights, sounds and tastes of India, Pakistan and Bangladesh mix and mingle. Meanwhile on the south side, Chicago’s Chinatown—one of the largest in the country—and Bronzeville boasts incredible public art and cultural history.

For architecture buffs, Chicago’s neighborhoods are a special treat. Visionary architect Frank Lloyd Wright spent the first 20 years of his career in Chicago, and it shows. Oak Park is home to more Wright-designed structures than anywhere else in the world. The Frank Lloyd Wright Trust offers tours of his Oak Park home and studio, as well as day tours around the city highlighting Wright masterpieces like Unity Temple and Robie House.


Before being overtaken by Los Angeles, Chicago was the nation’s second-largest city. The city’s cultural offerings, however, are second to none. Jazz and blues music were nurtured here in the early decades of the 20th century, and they remain woven into city’s soul. The Chicago Jazz Festival takes place yearly in early September in Millennium Park and jazz clubs around town keep the music going all year. A few of note include the Green Mill, Andy’s Jazz Club, Fitzgerald’s and the Jazz Showcase. If blues is more your style, follow in the footsteps of Muddy Waters, Howlin’ Wolf, Bo Diddley, and Buddy Guy. Literally, in this case, as Buddy Guy continues to play at his club, Legends. Other hotspots are the House of Blues, Lee’s Unleaded Blues and the New Checkerboard Lounge.

If the blues get you down, there’s always something here to make you laugh. The city is full of comedy clubs and improv theaters like iO or Second City, where generations of comedians have honed their craft before going on to Hollywood stardom.

And last but certainly not least, Chicago is a foodie town, with dozens of Michelin-star restaurants and James Beard award-winning chefs. Check out up-and-comers The Purple Pig or Girl & the Goat from Top Chef winner Stephanie Izard. Or stick with modern classics like Blackbird, Rick Bayless’ Fronterra Grill or Everest, perched on the 40th floor of the Chicago Stock Exchange.