I spent five days in downtown Chicago — here's why I found it hard to leave

Diverse and friendly, Chicago’s cultural scene is another great reason to visit this fun city, writes Aoife Barry

Sat, 15 Nov, 2025 - 01:00

Aoife Barry

In 2003, aged 20, I headed to Chicago for the rite of passage that is the J1. I somehow wrangled a job answering phones at ABC Radio on State St, and lived with a gang of friends in Lincoln Park. I’m not sure any photos of that time exist. In our pre-smartphone world, our Chicago adventure was lived solely for memory’s sake.

In those memories, Chicago was filled with towering skyscrapers that gave off an air of grandeur. Taking its elevated train, known as the L, through the city made me feel like a movie character. Everything, from portion sizes to parks, was bigger than back home. The city was beautiful and imposing — but welcoming and relaxed too.

So when the invitation comes to revisit Chicago to check out its arts and culture scene, I’m curious. My last time in the Windy City was 2013. I wonder how it’s faring in Trump’s America, and how the arts have been responding to it all.

What my five days in downtown Chicago show me is that the city from my memory still lives. It still boasts its ‘emerald necklace’ of parks; tourists still flock to Navy Pier. It still has the friendly attitude that made me feel so welcome. It’s still so stunning that it would make you gasp. And it still wears its diversity and history of immigration proudly.

I stay in the heart of downtown at L7 Chicago by Lotte. It’s a sophisticated mix of cosy minimalism and arty elegance, with a restaurant (Perilla Steakhouse) serving delicious Korean-inspired fare. My roomy room offers a view of Marina City, a favourite mid-century architectural gem of mine: twin apartment blocks that look like corn cobs. The hotel is abuzz with tourists, and the service is, as it tends to be in America, ultra friendly.

A block away is State St, home to big-brand shops and independents like Reckless Records. Around the corner is Millennium Park, a 24.5-acre green jewel that’s home to art installations like the mirrored Cloud Gate sculpture by Anish Kapoor, aka ‘the Bean’. Also in this patch are the Chicago Cultural Center, the Symphony Center (home to the Chicago Symphony Orchestra), and the Art Institute of Chicago.

My first cultural activity is dinner at Teatro ZinZanni, a cabaret-meets-circus performance inside a spiegeltent in the historic Cambria Hotel. It’s a light-hearted event with a few tricks up its sleeve.

Jetlag so far at bay, the next day begins with a walk down the Magnificent Mile, a delightful shopping-centric stretch of North Michigan Avenue. Just off the mile is the Museum of Contemporary Art Chicago (MCA), home to a huge Yoko Ono: Music of the Mind retrospective until February 11.

Ono’s a favourite artist of mine, and her message that ‘peace is power’ (emblazoned on the front of the MCA) is front of mind as I take in her videos, installations, and photographs. Art is never far from politics in Chicago — also on display at the MCA is Edie Fake’s The Free Clinic for Gender Affirming Care (2024-25), a mural showing an imagined facade for a clinic offering free transgender healthcare.

The entrance to the Art Institute of Chicago

After lunch at the MCA’s classy farm-to-table restaurant Marisol, it’s on to the Art Institute, which is so large you could dedicate an entire trip to it. I head past the two bronze lions that guard its entrance and on to iconic pieces like Georgia O’Keeffe’s Sky above Clouds IV and Grant Wood’s American Gothic, before racing over to the exhibition Elizabeth Catlett: A Black Revolutionary Artist and All That It Implies. This is a retrospective of her stunning, fierce lino prints and sculptures. Her work explores racism and class, and burns bright with its call for social justice.

When you’re in the home of one of the world’s greatest symphony orchestras, you can’t turn down the opportunity to see them. So that evening, I watch the spirited young Finnish conductor Klaus Makela at the helm for a lively performance by the Chicago Symphony Orchestra of Hector Berlioz’s Symphonie Fantastique. Heading down Michigan Avenue afterwards, amid hundreds of other audience members, is as much of a thrill as the performance. I feel, for a moment, like a temporary local again in this colourful, energetic big city.

A trip through the city on the Chicago Architecture Foundation Center River Cruise

The last time I was in Chicago, I took an architecture river tour. Queuing on my second day for the Chicago Architecture Foundation Center River Cruise, aboard the boat Chicago’s First Lady, I wonder how much could have changed since. Turns out: A lot.

This tour is a genuinely unmissable way to get to know Chicago. The guide brings us through Chicago’s history, from its original Potawatomi Native American inhabitants through to its early 19th century expansion and the Chicago Fire, glitzy Art Deco era, midcentury vogue for minimalism and on to today’s preference for glass-fronted skyscrapers. A highlight is the 365m St Regis Chicago by Studio Gang, which has empty ‘blow-through floors’ near the top, to keep it stabilised.

One of the most charming additions since my last visit is the Riverwalk: public areas with restaurants, wineries, boat tours, kayaking, and much more along the banks of the Chicago River. The CAFC River Cruise guide tells us that only a few years ago, the river smelled of sewage. What a transformation.

State Street Bridge on the Chicago Riverwalk

I grab lunch at The Exchange, a chic cafe in a former railway exchange on South Michigan Avenue. Upstairs are the offices of SOM, which has designed some of the world’s tallest buildings, including Chicago’s John Hancock Centre and the Burj Khalifa in Dubai. Thanks to Open House Chicago, run by the Chicago Architecture Center, I get a free tour of their Scandi-style offices.

I pass through a No Kings protest afterwards. Around 250,000 people are taking part, many holding placards that fuse humour with fury. But for all of the deep concern and anger on show, the atmosphere is welcoming and family-friendly. The crowd reflects the fact that Chicago is a hugely diverse city. Some areas are named after immigrant communities, like the Ukrainian Village. Bronzeville is the heart of Black Chicago, while Humboldt Park has a rich Puerto Rican history.

The same night as the No Kings protests, the annual Arts in the Dark parade lights up State St. My heart is warmed as 90 different arts organisations and collectives — from drill groups to Mexican dancers — perform in Halloween costumes for a multi-generational audience. It’s an exhilarating celebration of community arts.

Art is projected onto the Merchandise Mart's facade at night

It’s mid-October, but as warm as an Irish summer day. The humidity breaks in the evening as I sit watching Art on the Mart, a fun digital light display projected onto the 2.5-acre river facade of the Merchandise Mart building. Rain lashes down onto the nearby L tracks as a train rumbles past, sending flashes of light streaking into the sky.

It’s a soggy but short taxi ride to the West Loop for dinner at Alla Vita, a classy Italian-inspired joint. It’s a lovely introduction to the West Loop scene. If you’re a foodie, skip the deep-dish pizzas and check out the neighbourhoods for some proper Chicagoan fare. A trip to Pilsen Yards on the Lower West Side for tacos the next day makes me wish I had more time to explore this area, where Czech and Mexican communities have deep roots.

Inside the stunning Chicago Cultural Center

Sunday morning kicks off with a tour of the Chicago Cultural Center on Washington St, which is hosting exhibitions for the Chicago Architecture Biennial (running until February 28). The building is a tourist draw, but also functions as a community hangout spot. On a design level it’s a marvel, with two stunning, huge stained-glass domes. It offers free art exhibitions, a learning lab, and a shop selling work by local artists, handy for souvenirs.

After lunch at the Greek-inspired Avli on the Park (near another incredible Gang Studio skyscraper, Aqua), I take a quick trip to Wrigleyville, a sports-lover’s paradise that’s home to Wrigley Field. A short walk away is Northalsted, aka LGBT+ village Boystown, where the bars are hopping. Downtown is extremely walkable, but so many pretty, explorable neighbourhoods are easy to visit via the L train.

It’s hard to leave Chicago. On my last morning I take the obligatory selfie at the Bean, then head to the American Writers Museum on North Michigan Avenue. There, I learn about Chicago’s black newspapers and their fight for equal rights, as well as groundbreaking writers like Gwendolyn Brooks. One of the exhibits asks people to ‘share your family’s immigration story’ — a fitting fusion of history and art.

Then, for old time’s sake, I walk over to my former workplace on State St. I find the main entrance under construction. Next door, my old lunch spot Potbelly’s is also shut. So some things do change in Chicago, it turns out. Thankfully its open-hearted, artistic spirit remains.