Visiting Chicago
As the third-largest metropolis in the United States, set against the shores of Lake Michigan in the Midwest, the monumental city of Chicago has left its days of Al Capone and Prohibition far behind. After the Great Chicago Fire of 1871 leveled the downtown area, the city transformed into an architectural laboratory, drawing millions of immigrants, mostly from Scandinavia, all looking to stake their claim in the American dream. Long celebrated as a blue-collar powerhouse, Chicago was once the industrial heartbeat for the eastern half of the country, defined by its steel mills and stockyards. Famous for its blues music, a buzzing arts scene, and some 8,000 hot dog stands, the Chicagoans will tell you straight: this is the real America. Its motto, Urbs in Horto (City in a Garden), speaks to the high quality of life and green space integrated into the urban fabric. You will also have the chance to grab a deep-dish pizza, which can be two inches thick, while catching a game featuring the legendary Bulls.
Four distinct seasons define the year, featuring winters that are cold but manageable and summers that are warm with a steady lake breeze.
The Loop, an immense business district with hidden charms
Bounded by the Chicago River, The Loop packs in most of the city's iconic skyscrapers, such as the Willis Tower, the John Hancock Center, and the home of the Tribune, alongside museums and sprawling urban parks. This area is unpredictable and fascinating, where vibrant street art sits comfortably next to sculptures by masters like Chagall, Miro, or Picasso.
Discovering remarkable architecture
If you can, book one of the 85 guided tours offered by the Chicago Architecture Foundation (about $15). You will learn to distinguish the various schools of modern urban planning and see how the modernist style became the standard here. For a different perspective, the Chicago's First Lady Cruises river tour makes the city's forest of skyscrapers feel truly massive from the water. For a more active approach, try a kayak tour.
The Chicago Architecture Foundation center is free to enter and features an impressive scale model of the city. For a quick 15-minute overview, hop on the Brown Line at the Merchandise Mart station heading south. If you are interested in the city's criminal history, don't miss the Untouchable Gangster tour, which features costumed guides who fully lean into their roles.
Start your exploration at the stunning Chicago Cultural Center, a former neoclassical library turned exhibition space. You will be struck by the marble staircases, the Tiffany glass dome, and the pastel mosaics. On weekdays, it hosts free concerts. Next, head up to the Willis Tower (formerly the Sears Tower), standing at 1,450 feet, for a panoramic view of the Loop. Its Skydeck on the 103rd floor features exhibits on the city's history and icons. The brave can step out onto The Ledge, a glass balcony suspended over the street. Another exceptional vantage point is the John Hancock Center 360° Chicago Observatory. For a free alternative, head to the 9th floor of the Harold Washington Public Library. Nearby, don't miss the Auditorium Building or the Carsons Camp Store, housed in the opulent Sullivan Center (formerly the Carson Pirie Scott store).
Windy City, a place of endless possibilities
Art and culture
Make your way to Millennium Park, home to famous sculptures like the reflective Cloud Gate by Anish Kapoor, the scarlet Flamingo by Alexander Calder, and the stunning Crown Fountain by Jaume Plensa. The park connects to the lush Grant Park, which holds the world-class Art Institute. Fans of Impressionist and Post-Impressionist art will find plenty to admire here.
For a trip back in time, visit the campus of the University of Chicago, where the most famous student was undoubtedly Barack Obama. The neo-Gothic buildings, the Robie House, and the studious atmosphere offer a peaceful escape from the city noise.
Shopping
Shoppers should head straight for the Magnificent Mile, which hosts the most recognizable American brands. The busiest spot for retail is the Water Tower Place mall. Nearby, check out the elegant Wrigley Building, which takes inspiration from the Seville Cathedral. It is especially striking at night when fully illuminated.
Relaxation
If you are traveling with children, the John G. Shedd Aquarium is a standout. Free alternatives include the Lincoln Park Zoo and the Lincoln Park Conservatory.
In warmer weather, you can enjoy one of the 34 beaches in the city, accessible from the Navy Pier. Sunbathing at Oak Street Beach is a surreal experience, as you are lounging in the sand right in the shadow of the downtown skyline. If you have time, take a bike ride along the Lakefront Trail, where you will quickly forget you are in the middle of a major city.
When to go?
The best time to visit Chicago is during the fall.
How to get there?
Air Canada, Air France, American Airlines, Delta Airlines, Icelandair, Lufthansa, and United Airlines provide daily direct flights to Chicago.
How to get around?
Upon arrival at O'Hare airport, take the Blue Line from Terminal 3 (a 45-minute ride). Get off at the Clark stop for downtown. You can also use the Airport Express shuttle (about $30) or a taxi (about $50 depending on traffic).
Once you are in the Loop, walking is best. Otherwise, use the elevated train, known as the L Train. Because the city is so expansive, travel times can add up.
I discovered the Windy City during a weekend trip while I was on a university exchange program in Columbus, Ohio. Since people talk much less about Chicago than other North American megacities, I did not have high expectations for this visit. In the end, I was totally blown away (even more than when I first discovered New York a few years later). An impressive skyline, monumental buildings in terms of both volume and height, Lake Michigan, the Chicago River so wonderfully integrated into the city's modern urban planning... We spent 2 days walking non-stop around the city without ever getting bored. We ate well (okay, for good food, you have to be willing to drop a few dollars) and we had a great time partying.
In short, my best memory of that first quarter on Yankee soil!