When I first visited Chicago, I was thirteen. One, serendipitous trip with family left me gawking up at a green champagne bottle of a building (the Carbide & Carbon Building) and I knew—the Windy City would always have a special place in my heart. Since then, I’ve visited the city half a dozen times! But if I were a first-time visitor to Chicago once more, and only had the weekend to explore its charm, here’s how I’d plan it.
When is the Best Time to Visit Chicago?
I’ve had the pleasure of visiting Chicago in all four seasons—yes, even the frigid winter, but summer in Chi-Town is unmatched. Honestly, it’s the epitome of summertime in the States! With a heavy rotation of food and music festivals, boating and other water activities on Lake Michigan, scrumptious patio restaurants, and six professional sports teams, Chicago quite literally has it all.
Where Should You Stay in Chicago?
Stay near Grant Park. Bordered by Lake Michigan to the east and the Chicago River just a block to the north, Grant Park is a central, sprawling green space that is home to some of the city’s most iconic events, including Taste of Chicago and Lollapalooza. It also provides an ample base to view several attractions—the Chicago Riverwalk, the “Bean,” the Magnificent Mile, and Navy Pier—on foot. I recommend staying at the Hilton Chicago, a gorgeous, Gatsby-esque property that overlooks the park and the lake.
How Do You Get Around Chicago?
Take the “L” to get around. If you’ve ever seen a film set in Chicago, such as Divergent, The Fugitive, or While You Were Sleeping you’ll probably recall footage of an iconic above-ground train system bumbling along in the background. That system isn’t just a design feature, it’s the “L” (also known as the Chicago Transit Authority (CTA) rail system) and it’s the most reliable way to trek around the city besides using your own two feet. Flying into Midway? Ditch the rental car and take the Orange Line to Roosevelt Station. That’ll put you a block west of Grant Park.
The 9 Best Things to See & Do for a Weekend Trip to Chicago
Check out Millennium Park.
Nestled at the northernmost end of Grant Park, is Millennium Park. In this quaint corner, you can peruse various art installations, a garden full of vibrant perennials, the McCormick Tribune Plaza (which is converted into an ice rink during the winter holiday season) and the “Bean,” an interactive sculpture officially known as Cloud Gate. Adjust your line of sight just so, and you’ll see Chicago’s skyline reflected back in it! Go early (around 7 or 8 AM) to avoid the crowds.
Take a Chicago architecture river cruise.
Did you know that Chicago pioneered the skyscraper? Yes, the modern, steel buildings you see in just about every major U.S. city have Chicago to thank for their existence! The Chicago Fire of 1871 was so vicious that it leveled nearly a third of the city—but it became a mecca for several architecture luminaries, including Louis Sullivan, Frank Lloyd Wright, and Ludwig Mies van der Rohe. Taking an architecture cruise tour along the Chicago River is honestly the best way to get acquainted with the city!
Check out Navy Pier.
This one’s a toss-up for locals, but if it’s your first time, I’d say it’s worth checking out! Explore the shops, ride the ferris wheel, or simply gaze out at Lake Michigan. Pro tip: During the summer, Navy Pier hosts a fireworks show every Wednesday night at 9 PM and Saturday night at 10 PM.
Go museum-hopping.
For the history, art, or science aficionado, Chicago has plenty to offer. To begin, consider the Field Museum for natural history or The Art Institute of Chicago if you’re staying near Grant Park. Or if venturing out, consider the Griffin Museum of Science and Industry in Hyde Park.
Go to the beach.
Yes, you read that right, the beach. Sitting on Lake Michigan, Chicago has over 20 public beaches along the shoreline! If you’re near Navy Pier, you can easily visit Ohio Street Beach for gorgeous views of Willis Tower (also known as Sears Tower) and the surrounding cityscape. The two attractions are a short, five-minute walk apart.
See a baseball game.
The Windy City is home to not one, but two, professional baseball teams. Chance are at least one team will be playing at home when you visit, so why not go cheer them on? Snag tickets to a Chicago Cubs or Chicago White Sox game and enjoy this historic past time.
Grab a Chicago-style “dog” and a slice of deep dish pizza.
The Windy City is a foodie’s haven. That means Chicagoans are serious about their eats and have curated cuisines. Be sure to try Chicago’s take on the hotdog—an all-beef frank on a poppyseed bun, served with diced onions, tomato wedges, a dill pickle, relish, peppers, and mustard. (I usually hold the tomato, though!) And don’t skip out on a slice of pie—Chicagoans prefer deep dish with the tomato sauce on top!
Walk the Magnificent Mile.
Looking to shop until you drop? Head north along Michigan Avenue, crossing the Chicago River, and enter Chicago’s upscale shopping district, the Magnificent Mile. There are plenty of dining options nearby if you work up an appetite as well.
Visit Hyde Park.
Twenty minutes away by the Metra (Chicago’s commuter rail system) is a quaint neighborhood that has served as the home of the University of Chicago and several prominent figures— including President Barack Obama and his family, boxing legend Muhammad Ali, architect Frank Lloyd Wright, and Chicago’s first black mayor, Harold Washington.
Spend the afternoon roaming the Robie House (on the University of Chicago’s campus) which was designed by none other than Frank Lloyd Wright. Or stop by the new Obama Presidential Center. If you have children, consider the Griffin Museum of Science & Technology. End you trip at Promontory Point, observing Chicago’s skyline from a distance as you rest along the colossal limestone blocks that form the peninsula.
