As Nelson Algren once famously penned, “Chicago is an October sort of city even in spring.” While we’d be delighted to tell you that the Windy City boasts golden and rust-colored foliage year-round, it’d be more accurate to assume Algren was writing about the feeling the city gives you. Although you’ll feel small when walking in the shadow of the Willis Tower and while gazing at the behemoth cats inside the Lincoln Park Zoo, the city emanates a warmness that will make you feel like you’ve been there your whole life—especially through the many autumns of your life. Cozy up inside one of the best places to stay in Chicago and let the city’s welcome soak in as you gaze out over the skyline.
Things to do in Chicago
Let yourself wander aimlessly through the city; steely skyscrapers rise up all around you, but your feet will eventually carry you to Navy Pier. From the unique position of the pier, you can look back at the city and get a sense of its grandeur. A quick ride on the Navy Pier Ferris wheel will leave you feeling infatuated with the Windy City and its scenic views of Lake Michigan. Afterward, bid the choppy slate-colored waters adieu and head toward the Magnificent Mile. You’ll try your darndest to take it all in, but with sparkling lights announcing the names of department stores, artisan boutiques, art galleries, and quaint cafes, you’ll need more than a magnificent minute to explore all the shopping and entertainment the area has to offer.
You return shopping bags stuffed to the brim to your Chicago lodging but are still itching to explore the Midwestern city. Set out to see one of the most iconic spots in the city—Wrigley Field. Home to the Chicago Cubs, the stadium has seen more than its fair share of victories, losses, and die-hard fans pass through its hallowed halls. The crowd’s heartfelt cheers will have you sitting on the edge of your seat as men in white, blue, and red take to the mound to instill a bit of hometown pride. And while you might be tempted to load up on traditional baseball fare, such as a piping hot Chicago dog, you’re better off waiting until you exit the stadium to enjoy a Midwestern feast.
Eating and Drinking
The city is teeming with diverse culinary options to explore. But first things first, you need to try the dish that has become iconic in this region of the United States—the deep dish, that is. As you sit down at an unassuming pizza joint and admire its classic red cups, you overhear a local speaking to another diner. “I only eat here when I’m showing tourists around, real Chicagoans don’t eat deep-dish on the regular.” You laugh as the waiter nudges you and whispers, “He’s in here every week.” The dish might be carb-centric, but you find that locals and tourists alike are drawn to the doughy haven known as deep-dish pizza. Your mouth will be watering as you prepare yourself to take a bite of the flaky, buttery pizza crust cooked in a deep pan, topped with crumbling seasoned sausage, a mountain of gooey cheese, and homemade tomato sauce—an Italian cherry on top.
You’re not sure you can eat anymore, but as you walk through Chicago’s various neighborhoods, you feel yourself salivating once again. In Chinatown, your nostrils are accosted by the sweet and spicy smells of roast duck hanging in charming windows, while in Pilsen, you can’t help but guffaw over the array of Mexican eateries that call out to you with their colorful store fronts and promises of homemade tortillas. You decide to grab dinner in the West Loop; a decision your future self will thank you for. Known to be the neighborhood with the most contemporary restaurants, there’s always something new and delicious to sink your teeth into in the West Loop. Whether you’re looking for artisan charcuterie boards paired with a nice glass of red wine, comforting sauce-laden French food, or a cheeseburger that feels less dirty diner and more upscale American, you’ve come to the right place.
Green Spaces Galore
Arguably, once you’ve finished sampling the best cuisine the city has to offer, you’ll want to walk it off. Millennium Park presents the ideal space for an after-dinner stroll. Not only does the expansive 25-acre space offer numerous lawns where you can walk, sit, watch the clouds roll in, and lazily lay to read your favorite book, but numerous public art installations as well.
You’ll want to fetch your camera from inside your leather satchel as you walk about Millennium Park. The most iconic art piece at the heart of the park is Cloud Gate, better known to locals as The Bean. The massive stainless steel installation is representative of the city as a whole, though it might be gray and steely, it attracts thousands of visitors and has drawn admiration from locals and tourists alike.
Day Trips from Chicago
Now that you’ve figured out what to eat and where to stay in Chicago, you’re curious as to what other Midwestern treasures are in your midst. Rent a car and drive 148 miles northwest to Madison, Wisconsin. This charming city is oozing with personality, as well as its fair share of cheese curds and craft beer. Whether you spend your day out of Chi-town sampling the best brews the lakeside city has to offer or attending a live performance at the oldest venue in the city, Majestic Theatre, you’ll find you almost don’t want to leave. But the intoxicating promises of Chicago improv theatre and deep-dish pizza will have you returning to Illinois by the end of the evening.
That Toddlin’ Town
There are so many things to do in Chicago that you’ll need more than a few days there to soak in all the city has to offer. Reserve affordable accommodations with Travelocity today and prepare to experience the city of eternal Octobers—any time of year.