We first went to Chicago sometime in the late 80s. My dad went to take his masters at a university in a suburb north of the city, and he bought my mom and me to live in a small apartment for about a year and a half. I was barely a toddler then, so I only have the vaguest of my memories of those times. My sister was born sometime during our stay, which gives her dual American and Filipino citizenship. But even if she has been a couple of times to the U.S., she has never seen the town of her birth, much less Chicago. So when my dad had to go to a conference in Florida and then Indiana, we (except my younger brother, who isn’t yet eligible for leave from work) jumped on the opportunity to go a few days after him and take this time to explore the state we have personal history with. It’s some sort of a pilgrimage tour for us.

My mother is having a blast as she recalls our family history. We’re strolling along the banks of Lake Michigan in the Navy Pier. It’s a fine, cool day in the Windy City, where, naturally, we start our exploration of Illinois as we wait for our dad from the conference to arrive a few days later. Fall has not arrived yet, but the gray skies and the occasional lake breeze herald the tail end of summer. Physically, my mom is a far cry from how she was when we lived here. She now walks with a cane and can’t walk faster than a slow mosey. But … YOLO.

We leave my mom at a foodcourt inside a mall while I and my sister walk from the Navy Pier to the DuSable Bridge at the southern end of Chicago’s Magnificent Mile. This becomes my sister’s and my first proper impression of the city – photogenic, welcoming, and much more laidback than New York City. Art Deco skyscrapers tower over the streets that teem with history. The Wrigley Building, the Tribune Tower — they’re all here.

Every point of the map in this part of Chicago is acclaimed. The city speaks. But to properly hear it, we have to explore further. Today, though, after lunch, we need to return to our inn, rest and give our bodies opportunity to recover from jetlag.

Chicago is traditionally divided into 77 communities. The communities we explored the previous day were the Navy Pier and the Near North Side. Both are unabashedly commercial zones of the city, especially the Near North Side, where lies the Magnificent Mile, a historic thoroughfare lined by high-end malls and international chains. The most famous site in the area — and in fact the whole of Chicago — is the Navy Pier, with its lakeside views and a Ferris wheel (a Chicago product!) drawing about 8 million visitors a year (at least before the pandemic).

Today, though, we’re exploring the Chicago Loop, the city’s commercial and historic heart. We emerge from a basement parking lot to the Millennium Park, where the iconic Cloud Gate sculpture is. We take a few pictures in front of the large stainless steel structure, then proceed to the Loop itself. L trains run above the streets, snaking around buildings whose architecture transport one to a bygone era. The neighborhood’s name in fact comes from the loops these trains make around the area before branching out to different parts of the city.

Skyscrapers first rose from the streets of Chicago, so it’s little wonder that the city also boasts some of those with the most gorgeous architecture. Some of the notable are the Chicago Board of Trade, the Chicago Cultural Center, and the Rookery. My sister in fact wastes no time posing in front of a lot of these buildings, her spirit oozing with joy from the fact she’s reconnected with her roots.

After a lunch at a chicken fast food restaurant, we ride an L train to the Willis Tower. It was still called Sears Tower when we first went here in the 80s, and at that time it was the tallest building in the world. Now, it’s named after the insurance broker company that entered into a leasing agreement with the building in 2009. And it’s now the 23rd-tallest building in the world. Before ascending to the top of the tower, we pass through a series of murals showing the different aspects of Chicago — food, buildings, public art installations, notable people. At the end of the presentation, we ride an elevator dishing out some bits of trivia as we rise to the Skydeck at the 103rd floor. We do the obligatory photo ops at the Ledge, a glass box protruding from the building, allowing visitors to see the streets below.

We return to Chicago four days later, after we’ve reunited with my dad, who’s back from his trip to a conference in Indiana. I go on a bike tour in the northern part of Chicago, while my mom and sister return to Willis Tower with my dad. After my bike tour, we drive to the Ukrainian Village in the western part of Chicago. It’s a quiet neighborhood, housing one of the largest concentration of Ukrainians in the U.S. Ribbons with the colors of the Ukrainian flag are tied around trees in the sidewalk, and banners proclaiming solidarity with country are displayed prominently everywhere. Three Ukrainian churches can be found in N Oakley Boulevard: St. Volodymyr Ukrainian Orthodox Cathedral, Saint Nicholas Ukrainian Catholic Cathedral, and Sts. Volodymyr and Olha Ukrainian Catholic Parish. Near the last two are the Ukrainian Museum of Contemporary Art and the Ukrainian National Museum.

Five days later, we return yet again, this time with Sam, a former co-teacher of mine who’s now living in Bloomingdale, a Chicago suburb, with his wife and two kids. He has a couple of connections with the University of Chicago, so we take this opportunity to have someone tour us around campus. The university grounds is large, and we only cover a small portion the whole morning. The cold morning air, which heralds the start of the fall season, as well as the clear blue sky work well with the regale architecture of the university to give something of a stately English countryside vibe.

On one of our last nights in Chicago, I go to a game of the Chicago Cubs in the famed Wrigley Field. I’m more of a basketball guy, and I only have basic knowledge of baseball (though my cousins and I played the game during school breaks when we were in grade school). Nonetheless, I want to immerse myself in something local, and enjoying a game of a local team is what I thought of (I couldn’t find a Chicago Bears game that aligned with our schedule and the Chicago Bulls won’t be playing a regular season game until late October.

I arrive at the field just as the Phillies score. But three innings later, Yan Gomes ties the game, followed by Christopher Morel hitting a three-run home run that gave the Cubs a three-point lead. The field erupts in cheers, and I’m just so glad to be part of this experience. Under the cold autumn night surrounded by jubilant Chicagoans, I savor every moment.

P.S. The Cubs hang on to win the game, 4-2.