By April Drew
Some cities whisper their charm, but Chicago shouts it from the top of the Willis Tower. After living in a major U.S. city for nine years -New York- I arrived in the Windy City expecting busy streets, loud noises, and people too hurried to connect. But my assumptions about the home of deep-dish pizza, and its people, couldn’t have been further from the truth.
I spent seven glorious days in Chicago, home to 2.7 million people, in June 2025. Around every corner, a vibrant mix of history, culture and local hometown characters welcomed us as we explored from day into night. As an Irish person, I’m no stranger to friendliness, but the Chicagoans I met were just as warm and lively. They made time for us, shared stories of their ancestors, laughed with us over drinks, and eagerly answered every burning question about this incredible Windy City.
Chicago’s history runs deep, from its rebirth after the Great Fire of 1871 to its pivotal role in shaping American architecture and music, especially the blues and jazz, the pulse of its streets. It’s a city of resilience and reinvention, where every neighbourhood tells a story worth discovering, and it was my aim to discover every single bit of it during my seven day trip.
The moment I learned that IPW 2025 would be held in Chicago, I signed up as soon as registration opened. Living in the Midwest region of Ireland (Co. Tipperary), I was thrilled to fly directly from my “local” international airport, Shannon, to Chicago on United Airlines. My travel companion, Julianne, and I enjoyed Economy Plus seating (Row 8), which gave us a comfortable 3 to 5 extra inches of legroom; a real treat on the seven-plus-hour flight. We settled in with a few movies, savoured some delicious meals, and caught a bit of rest. We departed early in the morning from Ireland and landed just before lunchtime in Chicago. Not one to waste a moment, we grabbed an Uber from O’Hare Airport (just under $50) and headed straight to our hotel.
We stayed at The Palmer House Hotel, operating since 1871 (and rumoured to be the longest continuously operating hotel in North America) and also the birthplace of the iconic chocolate brownie, created there for the 1893 World’s Columbian Exposition. It’s where old world charm meets, well, old word obsessed tourists. It’s just fabulous. It even has a Starbucks on the ground floor. It’s elegant and delicious and if those walls could talk they would bring you right back to the roaring 20’s when so much naughty stuff went down. Some of the most famous jazz musicians in the world played in the Palmer room including Louis Armstrong and Ella Fitzgerald. The room was small but I wasn’t expecting anything bigger in a hotel located a stone’s throw from Magnificent Mile.
After dropping off our bags, we quickly changed into something more comfortable (it was 32 degrees when we landed) and headed straight for an uber chic lunch. On our way to the London House Rooftop Bar (15 minutes from the hotel) we strolled down through streets that were sparsely populated. We expected crowds of workers and tourists barging their way to their next destination but it never happened (in the whole week we were there). It nearly felt like we were on a VIP tour of the city the whole time. It was so enjoyable. Anyway, back to lunch. The London House Rooftop Bar was highly recommended both by my followers and online. It’s a fancy spot on the 22nd floor offering panoramic views of the city skyline, the Chicago River and Lake Michigan. An ideal location to get pics for the gram and it helps that the food was delicious (and reasonable).
Well-rested and refreshed, we were ready to tackle Day 2 head-on. I did wake at 4am for an hour or so but managed to go back to sleep again. First stop on our tour was breakfast in Wildberry Pancakes and Cafe (an 11 minute walk from the hotel and across from Millenium Park). Outdoor seating was an option but we chose the air conditioned restaurant. We ordered way too much but it was thoroughly enjoyable. Not cheap but when in Rome! Bellies full, we meandered across the road and into the very famous Millenium Park, Chicago’s vibrant downtown oasis, renowned for its iconic public art like The Bean. It has fantastic open spaces combining green lawns, interactive fountains and an outdoor concert venue. We happened across rehearsals for a classical concert taking place later that evening ,so we took a few minutes to sit and listen to the magnificent sounds propelling through the park, before continuing our exploration around, finally reaching The Bean. Like every other tourist, we spent about 30-40 minutes taking goofy, fun pictures, standing behind, beside and underneath it to get the right insta-ready pictures. I’m not sure I managed to get anything remotely cool but we had fun doing so. We crossed the road over to Lake Michigan for a nice leisurely stroll along its shoreline that stretched over 1,600 miles; isn’t that bananas. Further up Lake Michigan Drive are beaches where families gather at weekends to swim and have picnics or take their boats out. There really is such a great balance to Chicago, I can see why people love living here.
Next up was a visit to the Art Institute of Chicago to see the travelling Frida Kahlo exhibition- “Frida Kahlo’s Month in Paris: A Friendship with Mary Reynolds.” Our generic entry was covered by the City Pass which I was given as part of my trip to Chicago but we paid an additional $5 each to visit the exhibition. It finished in July. Between the exhibition and exploring other areas of the museum we spent just under three hours here.
It was back to the hotel for a quick change and we walked to Andy’s Jazz Club (23 minutes); a beloved Chicago institution, known for its atmosphere and live performances by top local and national jazz artists. It was $15 to enter and we had dinner while watching an enjoyable show that lasted about two hours.
Day 3 kicked off with a funky bagel experience just around the corner from our hotel at Hero, followed by a leisurely wander through nearby bookstores and pharmacies. You can’t visit the U.S. without stocking up on essentials you can’t easily find back home, think melatonin, Crest whitening toothpaste, and some strong pain relief! It started to drizzle and the temperatures had plummeted down to the early 20’s (and our Irish bodies were very thankful for this drop) but a little drizzle didn’t stop us, we’re Irish after all! So on with the plans. We first walked along the Chicago River, snaking between towering skyscrapers; it felt magnificent. We had nowhere to be so we just strolled and admired the whole city from below. It offered a moment of calm to our jetlagged Irish bodies.
The rain wasn’t going anywhere so we decided it might be a good time for a sweet treat. I hadn’t been to the Cheesecake Factory since I lived in NYC so it was time to treat ourselves. I dragged Julianne down through the streets of Chicago and there she was, and it didn’t disappoint. After indulging in all sorts of cheesecake flavours, I took myself up to the 360 Chicago Observation Deck (also part of the City Pass) located on the 94th floor of the formerly known John Hancock Center. Situated over 1,000 feet above street level, this is impressive. It was unfortunately cloudy the day I visited but I could still see for miles across the Chicago skyline and Lake Michigan. This is also home to the TILT, an experience that tilts the visitor 30 degrees over the city, offering a thrilling perspective from such a height. I did NOT do this!
Another outfit change and it was off to legendary comedy club and improv theatre, The Second City for a fantastic show. We got the train out to the Old Town and met a friend for dinner. I hadn’t laughed that hard in years. I would absolutely recommend putting this on your list. The sketch based show was new and it didn’t disappoint. The Second City has launched the careers of countless comedic icons including Tina Fey and Stephen Colbert.
Day 4 started off rocky, I woke up with the flu but that wasn’t going to stop me exploring this breathtaking city so off we set at 9am. Straight to Michigan Avenue to join a walking movie tour, given by a real life actor who has been living in Chicago for years. He brought us around several movie and tv show locations, think The Bear and Chicago PD.
After our tour finished, it was time for some delicious lunch overlooking the river. Beatnik on the River was just fabulous, a delicious range of freshly cooked food served promptly and enjoyed in a very chic surrounding. The décor itself is a feast for the eyes, blending modern style with artistic flair that perfectly complements the dining experience.
After a few hours of wandering through Chicago’s shops, it was time for the highlight of the trip: an evening on an architecture boat tour along the Chicago River. Despite the chilly air, the city I had explored by day had transformed into a living gallery of light and steel by night, with the illuminated skyline telling its own story. Drifting beneath historic bridges, I found myself completely immersed in the mind-blowing architecture. The soft narration and the river’s steady rhythm made me see the city all over again from a fresh perspective; it was utterly magical.
After spending the next day *(Day 5) and night in my beautiful hotel room nursing the flu, I was finally feeling much better on Day 6. After hours of meeting incredible travel brands and tourist boards from across the U.S., it was finally time to let loose and party. The House of Blues Chicago has been on my bucket list for ages, so spending the evening surrounded by the soulful sounds of legendary singer Darius Rucker (best known in Ireland for Wagon Wheel) was everything, and then some. I was swept up in the electric energy of his music; I felt completely immersed in the spirit of Chicago’s legendary music scene. And the evening didn’t end there, next up with a trip to the SkyDeck Chicago at the Willis Tower. Up we went 103 floors, soaring into the Chicago skyline. The city was lit up in a sea of twinkling lights stretching in every direction. Standing on the glass ledge in the dark made the experience even more thrilling, it was almost surreal, especially after a few glasses of wine!
After a full day of meetings on Day 7, it was finally time to soak up some quintessential Chicago culture with an evening at the iconic Wrigley Field for our last night in the Windy City. From the moment we stepped into the stadium, the energy was electric, the crack of the bat, the cheers of the crowd, and the sense of history woven into every corner of the ballpark. The Cubs brought the action on the field, keeping us on the edge of our seats, while the warm, clear weather made the experience even more perfect. Surrounded by passionate fans and the unmistakable charm of one of America’s most beloved stadiums, it was a thrilling and unforgettable night.
I was absolutely blown away by just how completely I fell in love with Chicago; the energy, the architecture, the people, and the way the city seems to come alive at every hour. With the convenience of a direct flight on United Airlines from Shannon Airport, I know it won’t be long before I return. Next time, I’ll be bringing my family along to share in the fun, tackling all the family-friendly adventures and experiences I didn’t get to enjoy this trip. Chicago has firmly stolen a piece of my heart, and I can’t wait to explore it all over again.
