ARCHITECTURE DREAMLAND AND ALL THAT JAZZ
Empower Your Living
November 15, 2025 · 11 min read
November 15, 2025 · 11 min read
On my overnight stop at Zurich Airport in Switzerland, I meet up with a dear friend who kindly equips me with warmer clothes for the colder temperatures awaiting me on the next leg of The Journey. On September 18, I board another plane—this time bound for Chicago, one of my favorite cities in the world.
I have to admit, with everything that’s been happening in the USA this year, I was hesitant about this stop. But after giving it a lot of thought, I decided that no one tells me what I can and cannot do. Besides, I had committed to cat-sitting for a friend while she attended a wedding—so Chicago it was. It was also clear that I would not use my Canadian passport to enter the US. Lucky me for having dual citizenship—and especially for holding a Swiss passport, one of the most sought-after documents in the world.
While still in Bali, I researched what was required to enter the US. Honestly, the information online was confusing. With a haunting feeling that I might be missing something—and with all the scary news in the media—I filled out the ESTA form. Right at the start, it felt like giving away all my rights as a human being. Quite unsettling. And even after answering all of the US government’s questions, I couldn’t shake the odd feeling that I might have forgotten to declare some imaginary misdemeanor. Not a pleasant experience, I can tell you.
Sunshine, Beach, and an Unpleasant Awakening
After over an hour at customs, my friend greets me with a huge smile and a bear hug. The Windy City welcomes me with sunshine and summer vibes—what a warm hello!
Expecting cooler weather, I’m pleasantly surprised. Chicago is basking in glorious late-summer temperatures, and I get to spend many days on the stunning beaches along the lakefront—just a ten-minute walk from the apartment. I keep up my Southeast Asian tan and cool off in Lake Michigan. It feels surreal and wonderful at the same time: an unexpected three-week extension of summer!
From Edgewater in the north—where my friend lives right by the lake—down to Jackson Park in the south winds the almost 30 km bike and pedestrian Lakefront Trail (see notes). What a brilliant way to make the lake accessible to everyone. We rent Divvy bikes and pedal all the way downtown, grinning from ear to ear. Half the trail—done! Feeling proud, we reward ourselves with a classic Chicago hot dog.
On our way back, we stop at one of the beaches along the trail to watch the sunset, hearts full of joy. We return the bikes, then treat ourselves to Tibetan momos and one of the best fresh mango lassis I’ve ever had at the new Kathmandu Café (see notes).
The rude awakening comes the next day when my friend sees her credit card statement: each bike cost more than USD 50 😳🥵. Apparently, we exceeded the time limit. No warning message, no option to switch to a daily rate of USD 18. Cheeky! I’d say customer happiness should matter more than squeezing a few extra dollars. Lesson learned—next time, I’ll read the small print. And from then on I took the bus or walked.
Cat Mama for a Few Days
After my first week in Chicago, it’s time for cat-sitting duty while my friend is away. Tegan and I already met during my short visit in November 2024. Although he’s very shy and rarely seen by my host’s friends, he seemed to like me right away—so I wasn’t worried.
I love cats for their independence. All Tegan really wants is food—but he also enjoys being brushed, loves cuddles, and sits quietly on my lap while I watch a movie. We make a great team, and I have to admit—I’m loving being his cat mama.
Anyone need a cat sitter? Call me up! 😄
All That Jazz
Chicago without jazz or blues? Impossible. My dad was a real jazz buff, and although I needed time to warm up to the sometimes not-so-harmonic tunes at first, once I found my kind of jazz, I was hooked. Especially the blues—gotta love it.
The first weekend already brings the Englewood Jazz Festival (link in notes) on Chicago’s South Side—five days of pure music, featuring loads of young and upcoming artists. And it’s all free!
At the community center in Hamilton Park, we’re greeted by the sound of music before we even step inside. The atmosphere is alive—vibrant colors, stunning African fabrics, feet tapping, people swaying, some already dancing. So much energy, so much soul.
A week later, while my friend is away, I attend the 19th Annual Hyde Park Jazz Festival (see notes)—two jam-packed days of music, also free. A $10 donation feels like a small thank-you for such a gift to the community.
The lineup is incredible, featuring both international artists and Grammy winners. One group that really touches me is The JuJu Exchange—childhood friends blending genres and addressing real-world issues through their music. Simply inspiring.
Then there’s Maurice “MoBetta” Brown—a bit of a wild child, but what a trumpet player! No wonder he won the national Miles Davis Trumpet Competition as a teen and later recorded with Aretha Franklin, Wyclef Jean, and Macy Gray.
As the sun sets and the music fills the air, people can’t resist moving. I join in—losing myself in the rhythm, shaking my hips like a Latina at heart, floating in pure joy. This is what freedom feels like.
For more jazz and blues venues see notes.
The JuJu Exchange
Maurice “MoBetta” Brown
John Primer & The Real Deal Blues Band (Rosa’s Lounge)
An Architecture Lover’s Heaven
While summer still lingers, I crave some city vibes. No matter how many times I’ve walked Chicago’s streets, its architecture never ceases to amaze me. I’m a huge Art Deco lover, and there’s plenty to admire here.
A fantastic way to dive deeper is through a tour by the Chicago Architecture Center (CAC, link in notes). Normally, I prefer exploring on my own, but their tours are exceptional—worth every dollar. I highly recommend first-timers in Chicago to book the “CAC River Cruise aboard The First Lady” to catch the sunset and see the city’s spectacular skyline illuminated (I did it last November). Hands down, it’s one of the best tours ever. You not only get a fresh perspective of the city but also plenty of insights into Chicago’s history and its magnificent skyline.
After reading “The Devil in the White City” by Erik Larson—a brilliant book based on true events during the 1893 World’s Columbian Exposition—I just had to take the CAC bus tour. Retired locals who adore their city guide us through sites tied to the book’s history, including chilling stories about North America’s first serial killer, H.H. Holmes, who prowled the city during the fair’s construction in Jackson Park.
If you enjoy crime stories mixed with history and a touch of architectural brilliance, read this book.
Frank Lloyd Wright: The Grand Seigneur of the Prairie House Style
You probably know the iconic Solomon R. Guggenheim Museum in New York City, designed by Frank Lloyd Wright (FLW, see notes). I’m a huge fan of his work and minimalist, nature-inspired style.
Wright’s signature “Prairie School” style (see notes) was shaped in Chicago, where he arrived in 1887. Working under Adler & Sullivan, and witnessing the city’s rebirth after the Great Fire of 1871, deeply influenced him. His attention to every detail—from furniture and carpets to lighting—is remarkable. You can see his Japanese inspirations throughout his homes.
On the last summer day, I visit his home and studio in Oak Park and explore the neighborhood. Even from a distance, FLW’s houses are unmistakable.
Another must-see is The Rookery downtown. Though not originally designed by Wright, he remodeled its stunning light court and lobby in 1905. The 11-story building by Burnham & Root is an architectural gem. Burnham being the Director of Works at the 1893 World’s Columbian Exhibition.
I could go on forever about Chicago’s architectural masterpieces—but really, you should experience it yourself. Maybe this travel update inspires you to give this underrated city a real chance.
Notes:
Lakefront Trail
Kathmandu Cafe
Englewood Jazz Festival
Hyde Park Jazz Festival
The JuJu Exchange
Maurice “MoBetta” Brown
Rosa’s Lounge
Kathmandu Cafe
Englewood Jazz Festival
Hyde Park Jazz Festival
The JuJu Exchange
Maurice “MoBetta” Brown
Rosa’s Lounge
Jazz Showcase
Green Mill (on my list to go when I return in April 2026)
Chicago Architecture Center
Frank Lloyd Wright
Prairie School & The Prairie Style
The Rookery
Green Mill (on my list to go when I return in April 2026)
Chicago Architecture Center
Frank Lloyd Wright
Prairie School & The Prairie Style
The Rookery
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