CHICAGO

The Windy City. The Second City. Chi-Town. The Third Coast. There are many nicknames for Chicago, but I always think of it as my kind of town. I am biased, of course; Chicago is one of two hometowns I claim, having lived there for most of the first ten years of my life. I still travel there frequently to visit family, and it remains, hands down, one of my absolute favorite places. There is a distinct pulse to the city that I can feel the moment I land at Midway or O’Hare. What makes Chicago so great? Is it the people? The cultural diversity? The architecture? The elegant grid of the streets? The food? The music? You could pick any one of these—and add a dozen more—to explain exactly why Chicago is such an incredible place to travel.

ABOUT CHICAGO

While researching this piece, I learned that the name “Chicago” derives from the French interpretation of the Miami-Illinois word shikaakwa, which translates to "wild garlic" or "skunk." This likely referred to the pungent wild leeks that once carpeted the marshy riverbanks. The city's first non-Indigenous settler was Jean Baptiste Point du Sable, a man of African descent who built a prosperous farm near the mouth of the Chicago River and Lake Michigan in the late 1780s. Following the Treaty of Greenville in 1795, Native American tribes ceded the land to the U.S. military, and Fort Dearborn was established shortly after.

In 1829, the city began to take shape in the elegant, grid-like configuration we know today. Chicago quickly evolved into a bustling transportation hub, drawing Yankee settlers eager to cultivate the fertile farmlands of Northern Illinois. The opening of the Illinois and Michigan Canal in 1848 marked a massive turning point, carving out a continuous shipping lane from Lake Michigan all the way to the Mississippi River and the Gulf of Mexico. Capitalizing on its central geography and unparalleled water access, Chicago became the nation's premier crossroads for shipping, rail, and commerce, causing the population to explode from the 1840s onward.

Disaster struck in 1871 when the Great Chicago Fire claimed 300 lives, destroyed 18,000 buildings, and left a third of the city’s population homeless. Yet, Chicago survived and rebuilt with astonishing speed. From the literal ashes of the fire, the modern metropolis was born. Alongside New York, Chicago pioneered the skyward movement, erecting the world's very first skyscrapers. A thriving, iconic skyline rapidly took shape along the shores of Lake Michigan and the winding curves of the Chicago River.

By the mid-20th century, a massive influx of World War II veterans and displaced European immigrants fueled an unprecedented economic boom, triggering another wave of architectural marvels. In 1974, the Sears Tower (renamed Willis Tower in 2009) was completed, holding the title of the world's tallest building for nearly a quarter-century. Today, amidst a stunning mosaic of skyscrapers and architectural masterpieces, stands a city weathered by time but aged to perfection. The people of Chicago form a vibrant patchwork of ethnicities and languages, all proudly calling themselves Chicagoans. As the third-most populous metropolitan area in the United States, Chicagoland boasts a robust population of 9.44 million residents.

CHICAGO CLIMATE

Summers in Chicago are hot and humid, with daytime temperatures averaging in the 80s and 90s. Spring and fall are beautifully fleeting seasons with much milder weather. Then, there is winter in Chicago. To put it simply: it is bitterly cold. The fierce winds whipping off Lake Michigan deliver some of the harshest, most piercing blasts of arctic air you will ever experience. While snowfall is a regular occurrence and the city is masterfully equipped to handle routine accumulations, major blizzards can still bring the metropolis to a grinding halt.

Fun fact: I vividly remember the brutal winter of 1985. I was just a little kid, bundled up in a thick snowsuit over what felt like twenty layers of clothes. For years, I remembered the actual temperature—not the windchill factor—being around -30 degrees. Whenever I told that story later in life, I always worried it sounded like a classic childhood exaggeration. Nope—it actually happened. On January 20, 1985, the thermometer plummeted to a bone-chilling negative 27 degrees, courtesy of an extreme weather event we now commonly known as a polar vortex. Dress warmly, my friends!

WHERE TO STAY

Chicago is a massive metropolis sprawling across roughly 234 square miles. Since most visitors prefer to avoid the outer suburbs, it is best to stick to the vibrant downtown core. So, where should you stay? Personally, I like staying close to the subway system—or as we locals call it, the "L"—to navigate the city with ease. Choosing the perfect base is all about balancing your budget with proximity to the activities on your itinerary.

• River North: A sophisticated neighborhood packed with high-end hotels and an incredible dining scene. Bavette’s Bar & Boeuf and Rick Bayless's Frontera Grill are absolute culinary standouts here.

• The Loop: This is my personal go-to area because its central location puts you at the heart of everything. The Loop features the scenic Chicago Riverwalk, the historic Theater District, Millennium Park, and endless architectural landmarks.

• West Loop: A trendy, buzzing neighborhood that has evolved into a world-class culinary hotspot, packed with eclectic restaurants along Randolph Street's famous "Restaurant Row."

• Streeterville: An upbeat waterfront area located steps away from the iconic Navy Pier and the premier shopping along the Magnificent Mile.

• South Loop: A dynamic, newly revitalized district that puts you incredibly close to the Museum Campus—home to the iconic Field Museum, Adler Planetarium, Shedd Aquarium, and Soldier Field.

For most travelers, The Loop—named for the historic circuit of elevated tracks where the "L" trains run—is the prime location to stay. From here, you are within easy walking distance of almost every major downtown attraction, including the soaring Willis Tower, while remaining steps away from both the gorgeous lakefront and the riverfront.

CHICAGO FOOD

Death row inmates are famously granted a final meal request before execution. While I certainly hope I am never in a position to choose a "last meal," if I were, it would easily be a Chicago Italian beef—"baptized" in gravy, loaded with both sweet and hot giardiniera peppers—alongside a classic Chicago-style hot dog, and a side of crinkle-cut fries with a warm cup of cheese sauce. I simply could not be more quintessentially "Chicago" if I tried.

Chicagoans take their Italian beef incredibly seriously. I recently had a debate about a Middle Tennessee restaurant that boasts authentic "Chicago-style" food. They get it close—really close—but the flaw is always the thinness of the shaved beef. Much like Italy protects its authentic DOP products, I firmly believe a true Chicago beef must be shaved to a precise millimeter to earn the title. So, who makes the absolute best? If you want the ultimate combo of both Italian beef and hot dogs under one roof, my vote goes to Portillo’s. Ask ten different locals, and you will get ten different answers ranging from Al’s #1 to Tony’s or Buona. The ultimate takeaway is simple: you cannot leave the city without trying both.

Then, there is the broader Italian dining scene. When I brought my husband to Chicago for his very first visit in 2016, I took him to an authentic local Italian restaurant. His mind was so thoroughly blown that he flat-out refused to step foot inside an Olive Garden for the next year. The secret is to bypass the national chains and seek out independent neighborhood joints.

Beyond the beef and dogs, the city's culinary landscape is legendary. While global tourists flock to Chicago for deep-dish pizza, true locals know that our square-cut, ultra-thin tavern-style crust is the real hometown hero. For dessert, a trek to the Northwest Side for a slice of Eli’s Cheesecake is mandatory (and they ship nationwide!). From neighborhood delis to world-class gastronomic masterpieces like Alinea, Frontera Grill, Girl & the Goat, and Bar Mar, Chicago is a playground for your palate. Whatever brings you to the Windy City, make sure you come hungry.

CHICAGO TRANSPORTATION

Chicago is a highly drivable city—assuming you know exactly where you are going. Because I frequently visit family on the Northwest Side, having a vehicle is always a necessity for my specific trips. However, can you comfortably explore Chicago without a car? Absolutely. Taxis and rideshares are ubiquitous, and the city boasts one of the most comprehensive public transportation networks in the world: the Chicago Transit Authority (CTA).

Conveniently, both major airports connect directly to the train system. From O’Hare, the Blue Line takes you straight into the city, while the Orange Line services Midway, whisking you into the heart of downtown Chicago in about 30 to 45 minutes. The train routes are color-coded and incredibly easy to navigate. To maximize your budget, you can purchase unlimited-ride passes for 1-day, 3-day, 7-day, or 30-day periods, which grant you unrestricted access to both the "L" trains and the city buses. For real-time updates, head directly to transitchicago.com to access official route maps, fare details, and train trackers.

WHAT TO DO IN CHICAGO

The short answer? Everything. The city is packed with an overwhelming amount of things to see and do. If I had to give just one ultimate recommendation, it is to take an architecture cruise on the Chicago River. It is hands-down the best experience in the city, offering a masterclass in both Chicago's history and its soaring skyline. If you can line up your cruise with the golden hour, watching the sunset bounce off the glass and steel towers is absolutely spectacular.

• Willis Tower (formerly Sears Tower): I still catch myself calling it the Sears Tower—I just can't help it! Once the tallest building in the world, it stands like a beacon over the city. As a child, I remember peeking around street corners, always hoping to catch a glimpse of it in the distance. It is an iconic landmark and well worth a trip to the Skydeck at the top.

• 875 North Michigan Avenue (formerly the John Hancock Center): Located further north on Michigan Avenue, this engineering marvel offers a view that—unpopular opinion—is actually better than the Willis Tower. Because of its location, you get an unparalleled view looking straight up and down Chicago's stunning Gold Coast lakefront. If it’s your first time in the city, check out the Willis Tower. If you have the time for a second view, do not skip this one.

• Museums. Chicago boasts some of the finest museums on the planet. The majestic Field Museum of Natural History sits on the scenic Museum Campus, a lakefront park that also houses the iconic Shedd Aquarium and Adler Planetarium. Housed in a gorgeous, neoclassical building of white Georgian marble, the Field Museum protects precious pieces of our world's natural history.

  
  

  Just a short trip from the Museum Campus is the Art Institute of Chicago, home to one of the greatest global collections of art. Guarded by two famous bronze lions flanking the grand outdoor staircase, the galleries inside hold historic masterpieces from legendary artists like Vincent van Gogh, Henri Matisse, Claude Monet, Grant Wood, Marc Chagall, Andy Warhol, and Salvador Dalí, to name just a few. If you have extra time, the Museum of Science and Industry (in Hyde Park) and the Chicago History Museum (in Lincoln Park) are absolute gems.

To the east of downtown lies the vast expanse of Lake Michigan. So much of the city's energy is concentrated along this glorious shoreline. Here are the best ways to enjoy its ever-changing hues:

• Take a Boat Tour: Beyond the river cruises, many architecture tours extend out through the lock system into Lake Michigan itself. Departing from Navy Pier or Michigan Avenue, these cruises offer a truly majestic view of the complete Chicago skyline. 

• Navy Pier: Located in the Streeterville neighborhood, this historic pier juts out into Lake Michigan. It is home to the soaring Centennial Wheel, alongside a children's museum, shopping, restaurants, and the acclaimed Chicago Shakespeare Theater.

• Grant Park: Just south of the pier lies this massive, 300-plus-acre urban park. Affectionately known as "Chicago's Front Yard," it encompasses the Museum Campus, Millennium Park, and the grand Buckingham Fountain. It features excellent walking and running trails and serves as the epicenter for massive city events like Lollapalooza and the Taste of Chicago.

• Riverwalk. The Chicago River is the entire reason Chicago became a metropolis. Early traders and settlers were drawn here because the river—via interconnecting tributaries and modern canals—effectively linked Lake Michigan all the way to the Mississippi River and the Gulf of Mexico. Today, the Chicago Riverwalk, built along the south bank of the river's main stem, is a beautifully landscaped pedestrian oasis packed with vibrant bars, outdoor restaurants, and kayak rentals directly beneath the skyscrapers.

Along Michigan Avenue lies the world-famous Magnificent Mile. This buzzing 13-block stretch features high-end luxury shopping, flagship stores, upscale dining, and beautiful historic architecture. If massive premier brands aren't your style, head into the neighborhoods to explore eclectic, independent boutique shopping. North Clark Street in Andersonville, alongside the trendy streets of Wicker Park, Bucktown, Old Town, and Lincoln Park, are perfect for finding unique local treasures.

THE NEXT TIME I GO.....

Chicago is truly one of our nation's greatest metropolises. Whether you visit for the world-class food, the art, the rich history, or the premium shopping, this vibrant city offers an endless array of experiences.

So, what will I be doing the next time I return? Unsurprisingly, I plan to eat my way through some incredible local spots. First on the list is a mandatory stop at Portillo's to conquer my ultimate hometown order: a Chicago-style hot dog dragged "through the garden," a "wet and baptized" Italian beef sandwich loaded with hot and sweet peppers, and a side of crinkle-cut fries with warm nacho cheese. Can I actually finish all of that in one sitting? Absolutely not. Will I try anyway? You bet.

For a classic Italian night out, I always love dining at local staples like Carmine's or Rosebud on Rush. The Purple Pig is another absolute standout on Michigan Avenue that I can't pass up. I am also thrilled to try a few legendary spots I've somehow missed on past trips, such as booking a table at Bavette’s Bar & Boeuf in River North and embarking on an epic dim sum dumpling crawl through Chinatown.

Beyond the food, what does my next trip hold? I’m as eager to find out as you. My all-time favorite cultural institutions, the Field Museum and the Art Institute of Chicago, are both on the itinerary, and I am eager to finally check out the Museum of Illusions and the historic Newberry Library.

Yet, regardless of what specific sights I map out, the simple truth is that the absolute best time in Chicago is found by just wandering down the sidewalk in any direction, looking up, and letting the electric energy of the city enfold you.