The first record my mother ever owned was a 78 of Route 66 by Nat King Cole. It was sent to her when she was 15 by a man she met on a train going from Florence to Konstanz in 1955. She didn’t think there was anything strange about a grown man chatting up a teenager on a train, but the record gave her a lifelong curiosity to experience the Mother Road for herself. By happy coincidence, I won a competition prize of two tickets on United Airlines to Chicago, the start of the US’s most famous road. Despite living in the US for nearly a decade at various stages of her life, Mam had never been to Chicago, so this was the perfect opportunity. Plus, I knew she had always wanted to visit the Art Institute and see for herself the city that gave us the first skyscrapers. Chicago skyline However, when I suggested the trip, she hesitated. The US was fully engaged in its war with Iran, and the US America she remembered felt very different from the one making headlines. The political climate seemed febrile, the news cycle relentless and, at 85, she wasn’t entirely convinced this was the moment to be crossing the Atlantic. But she also understood that opportunities don’t come around forever. In truth, so did I. We haven’t lived in the same country for 40 years. We speak often and I visit her in her home in Italy regularly, but there’s a difference between knowing someone and knowing the rhythms of their daily life. In recent years she has developed an unlikely obsession with all things Korean, sparked during Covid by a steady diet of Korean dramas on Netflix. Since then she has made an annual pilgrimage to South Korea, immersing herself in a culture she finds endlessly fascinating. She insists on making those trips alone. Widowed since 2018, this is her way of holding on to a sense of freedom and self-reliance that she has no intention of giving up any time soon. At 85, she remains fiercely independent and increasingly inclined to explore the world on her own terms. I knew there weren’t going to be too many opportunities to do a proper trip with her. And so we found ourselves on the corner of Michigan Ave and East Adams Street in Chicago’s Loop, the historic downtown area that gets its name from the elevated train line, the L, that loops around the district. This is where Route 66 begins its long journey southwest to the Santa Monica Pier in Los Angeles. We were joined by Jonathan Orlov of Chicago Greeters, a volunteer-led programme that pairs visitors with local residents for personalised walks. Jonathan is a semi-retired architect, and he brought along his 91-year-old dad, Chuck, whose parents had emigrated from Latvia at the turn of the 20th century before settling on the West Side. Between them they brought Chicago to life. They talked about the city’s most famous buildings, pointed out features we would probably have ignored and, with great relish, told stories of what made Chicago distinctly Chicago. Outside Berghoffs, the city’s oldest restaurant, Chuck told the story of how this staunchly German joint that opened in 1898 refused to serve women until 1969, when activists led by Gloria Steinem sat at the bar and refused to leave until they got a drink. Berghoff Around the corner, Jonathan took us inside the old Chicago Athletic Association building, to show us the club’s original logo on one of the interior walls – a red, encircled “C” that then club member Bill Wrigley (of chewing gum fame) “borrowed” for his new baseball team, the Chicago Cubs, which remains their logo to this day. We made our way on to Chuck’s old turf on the West Side, and when I mentioned that my dad had been a huge jazz fan, he guided us to a shabby evangelical church on Roosevelt Street. “This used to be the Central Park Theater,” he told us, “and I think Benny Goodman played here.” Chuck was right. Goodman hadn’t just played there, he had his first ever gig there, as a precocious 12-year-old in 1921. We stopped for lunch at Lulu’s, a classic diner that serves burgers and Chicago-style beef dogs. On one of the outside walls is a huge mural commemorating the centenary of Route 66, which runs outside. We all had Polish dogs with all seven of Chicago’s traditional toppings, including neon green sweet relish, pickle spear and celery salt. No ketchup, though: in Chicago, Chuck explained, just asking for it is enough to get you thrown out of a place. He told us how, during the Depression, ketchup was used to mask the smell of rancid meat, so it became a point of pride among reputable vendors to never serve it. We followed his advice that evening at Wrigley Field, where we loaded up on beef dogs ahead of Mam’s first-ever live baseball game. It was a pretty lacklustre affair (the Cubs stumbled to a win over the hapless Philadelphia Phillies), but the spring weather was perfect and the atmosphere just right. “It’s nice here, isn’t it?” I wondered aloud to Mam. “It’s amazing how far away the war feels when you look at all this,” she replied. She was right. It did feel worlds apart from the turmoil and cruelty of an administration fumbling its way through an erosion of America’s reputation. For the first few days, I wanted Mam to experience Chicago at its cinematic best, so we stayed in the grand old Hilton on Michigan Avenue, a monument to a time when American hotels were built to impress entire cities. In 1959, the gold-leaf ballroom hosted Queen Elizabeth II and 7,200 guests for dinner; in 2008 Obama assembled his first cabinet here. The Bean by Anish Kapoor, officially Cloud Gate For us, the hotel was a great base from which to strike out and explore the city’s greatest hits. In Millennium Park across the street, Mam surprised me when she recognised the Bean as the work of Anish Kapoor, declaring herself a big fan. At the Skydeck in Willis Tower, she showed nary a nerve while standing on the glass ledge 103 floors above the ground. I clearly didn’t get my fear of heights from her. Union Station At Union Station, she happily posed on the staircase made famous in The Untouchables. She embraced her inner social media influencer and spread her arms beneath the angel wings on Plaza of the Americas. Plaza of the Americas She loved the architecture boat tour with First Lady Cruises. In the Art Institute, Mam fulfilled a lifelong ambition to see George Seurat’s A Sunday on La Grande Jatte and Hopper’s Nighthawks in person. There was so much more to see, but by then Mam was exhausted. She had been tired after the first day, but in my excitement to show her everything I barely noticed. Not that she complained. Instead, I gradually realised that crossing the street took almost as long as the green man stayed lit. At the end of day two, Mam casually remarked that we’d walked 14km that day. It was time to re-evaluate our schedule. Luckily, we were set to leave the dense canyon of skyscrapers for Andersonville, an old Swedish neighbourhood about 10km north of downtown. Chicago is really a city of neighbourhoods – 77 of them. Andersonville is the city dialled down to a more human scale, a proudly local place full of independent shops and bars, and with a strong LGBTQ+ representation. It’s also where the fault line between Chicago and the Trump administration felt very visible. A handful of shops had “F**k Ice” signs in their windows, while others had notices declaring that Ice agents could only enter with a warrant. 'Fuck Ice' signs Our home for the remainder of the trip was the Guesthouse Hotel, an elegant property with beautifully outfitted self-catering apartments. We checked in and then ambled up Clark Street, Andersonville’s main artery. Accommodation There’s a point on any trip with your mother where you both quietly forget you’re no longer parent and child, but two adults with very different ideas about what constitutes “a nice day out”. At the University of Chicago campus in Hyde Park, on the city’s south side, I pointed out the spot where the opening scene of When Harry Met Sally was shot – where Meg Ryan and Billy Crystal meet for the first time. Clearly it was more interesting to me, because she humoured me with a motherly “ah” that didn’t disguise her lack of interest. We were there to visit the Frederick C Robie House, Frank Lloyd Wright’s Prairie-style masterpiece, which had Mam’s complete attention. Mealtimes were given over to reminiscences and a running commentary on how surprisingly good the food was in the US (she is an Italian living in Italy), coupled with repeated observations that the portions were too large. A Caesar salad at the Dearborn in the Loop (owned by sisters Amy and Clodagh Lawless from Galway) drew a verdict that this could do for breakfast, lunch and dinner. At the southern-style Big Jones on Clark Street in Andersonville, we had a chuckle when my (huge) fried chicken arrived. The waiter explained that the birds came from a single Amish farm downstate. “Do they farm the world’s largest chickens?” we asked. He didn’t miss a beat. “Who knows?” he said. “Maybe.” Chicago portions I was also keen to introduce Mam to two Chicago staples with Italian roots: deep-dish pizza at Lou Malnati’s and an Italian beef sandwich at Bongiorno’s. She approved of both, although they reinforced her belief that Americans have never knowingly served a portion that couldn’t feed a family of four. By week’s end Mam had fallen completely for Chicago. How beautiful, interesting and clean it was. How friendly people were. She was exhausted, but deeply satisfied with everything. The day after we got home, she told me she was going to take it easy for a few days. Once again I felt bad for the pace we kept and apologised, but she was having none of it. “This is one of the best trips I’ve ever had,” she said. As it turned out, all that walking left me with an aggravated knee injury that is still giving me grief two months later. Mam, meanwhile, recovered just fine. At 85, she came through our Chicago adventure in better shape than I did – and with memories that, hopefully, will last a lifetime. For more information on Chicago, check out choosechicago.com