Chicago—where skyscrapers meet deep-dish pizza, jazz fills the air, and the people are as diverse as the city itself. There’s something about this city that grabs you. Whether it’s the iconic skyline, the historic neighborhoods, or the endless food scene, Chicago has a vibe that’s unmistakably its own. With a history rooted in innovation and resilience, this city invites you to explore everything from its famous architecture to its hidden gems.
Start with the Heart of Chicago: The Loop
You can’t visit Chicago without first taking in The Loop, the city’s downtown core. It’s home to some of the city’s most iconic landmarks, and it’s a great place to start your adventure.
Millennium Park: First stop: Millennium Park. It’s a must-see for any visitor, especially because of the famous Cloud Gate sculpture (aka “The Bean”). The reflective surface gives you a cool perspective of the skyline, and it’s a great photo op. Don’t rush past it—there’s something captivating about how the city’s reflection distorts in the shiny surface. Pro tip: If you’re there during the summer, check out the free concerts or outdoor movies.
Art Institute of Chicago: Just a stone’s throw from Millennium Park, the Art Institute is one of the oldest and largest art museums in the U.S. From ancient artifacts to modern masterpieces, it’s a must-visit for art lovers. Even if you’re not an art aficionado, it’s hard not to be awed by the impressive collection. Tip: If you only have time for one room, don’t miss the American Art Collection—it’s got some real gems.
Willis Tower Skydeck: For a jaw-dropping view of the city, head up to the Willis Tower Skydeck (formerly the Sears Tower). Standing at over 1,300 feet, it’s one of the tallest buildings in the world. Pro tip: Brave enough to step out on the Glass Ledge? It’s a terrifying but exhilarating experience—you’ll get a view of the city under your feet!
Chicago’s Neighborhoods: Discover the Real Windy City
While the Loop is where the action happens, Chicago’s neighborhoods are where you’ll find the real heart and soul of the city. From deep-dish pizza to vibrant street art, each area offers something unique.
Wicker Park/Bucktown: These neighborhoods are where the young and creative crowd hang out. Wicker Park is full of indie shops, quirky cafes, and street art. The vibe here is energetic, and you’ll find plenty of spots to spend an afternoon browsing, people-watching, and enjoying local art. Bucktown, right next door, has a more laid-back, residential feel but still boasts fantastic restaurants and bars. Check out The Violet Hour for craft cocktails in an intimate setting.
Lincoln Park: This neighborhood is a blend of green spaces, boutiques, and excellent restaurants. Stroll through Lincoln Park itself (the park, not the neighborhood) to catch a glimpse of the skyline framed by lush gardens and paths. If you’re into animals, the Lincoln Park Zoo is a great spot, and best of all, it’s free. Pro tip: Spend some time at The Second City for a night of comedy—this place has launched the careers of some big names like Tina Fey and Steve Carell.
Pilsen: Known for its vibrant Mexican culture and colorful murals, Pilsen is an up-and-coming neighborhood with plenty of character. It’s a fantastic area to explore if you want to get a taste of Chicago’s Latinx culture. The murals here are Instagram-worthy, and the food—especially at places like Carnitas Uruapan—is absolutely delicious.
Chicago’s Food Scene: A Culinary Mecca
If there’s one thing Chicago is famous for, it’s food. The Windy City offers everything from high-end dining to street food that’s become an institution.
Deep-Dish Pizza: Chicago’s deep-dish pizza is legendary—and for good reason. The crust is buttery, the sauce is tangy, and the cheese…well, it’s just glorious. Lou Malnati’s is a local favorite, but if you want a slice of history, try Giordano’s. It’s a meal in itself, so come hungry. Pro tip: Don’t expect New York-style thin crust here. This pizza is more like a savory pie!
Chicago-Style Hot Dog: A true Chicago hot dog isn’t complete without mustard, onions, relish, a pickle, tomato slices, and a dash of sport peppers—all piled on a poppy seed bun. If you’re really feeling adventurous, head to Portillo’s, which has perfected the art of the Chicago dog. Just remember, no ketchup!
Italian Beef Sandwich: A local classic, the Italian Beef sandwich is made with thinly sliced roast beef, dipped in gravy, and served on a roll with giardiniera (pickled vegetables). Al’s Beef is where you’ll find some of the best. Pro tip: Ask for your beef “wet” if you want that extra gravy soaked into the bread.
Ethiopian Cuisine: Chicago is home to one of the largest Ethiopian communities in the U.S., and you’ll find some seriously flavorful dishes in neighborhoods like Edgewater and Uptown. Demera is a top spot to dive into a traditional Ethiopian feast with injera and spiced stews.
Chicago’s Outdoors: Parks, Lakes, and Stunning Views
Though Chicago is a major urban hub, it doesn’t lack green space. In fact, there are a few standout outdoor spots that make this city feel more connected to nature than you might expect.
Lake Michigan: Chicago’s waterfront along Lake Michigan is stunning. The Chicago Lakefront Trail offers 18 miles of scenic paths for biking, walking, or jogging, with beautiful views of the skyline and the lake. Pro tip: If you visit in the summer, rent a bike and ride all the way to Oak Street Beach to cool off.
Grant Park: Chicago’s “front yard,” Grant Park is home to some of the city’s most iconic landmarks, like the Buckingham Fountain. It’s a great place to stroll or have a picnic. If you’re visiting in the summer, check out Lollapalooza, one of the largest music festivals in the country.
Quick Tips for Visiting Chicago
Dress in layers: Chicago is known for its wind (hence the nickname “The Windy City”), and it can get chilly even in summer. Dress in layers, especially if you’re planning on being outside by the lake.
Public transportation is your friend: Chicago’s L train system is easy to navigate and affordable. It’s also the best way to get around the city, especially if you’re exploring multiple neighborhoods.
Don’t rush: Chicago is a city best enjoyed at a slower pace. Whether you’re savoring a meal or taking in the architecture, make time to explore and really experience the different vibes of each neighborhood.
Take the architecture tour: Chicago is known for its architecture, and the Chicago Architecture Foundation River Cruise is an excellent way to learn about the city’s storied past and its bold, modern buildings.
Final Thoughts: Chicago’s Charms Will Stay with You
From the high rises of downtown to the eclectic neighborhoods full of character, Chicago is a city with a vibe all its own. It’s where history meets innovation, where the food is as diverse as the people, and where the music never stops. Whether you’re indulging in a deep-dish pizza, soaking in the skyline, or walking through one of its many parks, Chicago has a way of welcoming you and making you want to come back for more.
