CHICAGO: Uncovering the Soul of the Windy City
Zeke and Terri enjoying the architecture tour by boat (September 2024)
Four nights in Chicago taught us that the best city experiences happen when you venture beyond the typical tourist checklist. While we couldn't resist classic photo ops like "The Bean," our September adventure revealed layers of Chicago that surprised and delighted us at every turn.
Our journey began with baseball, because what's more quintessentially Chicago than that? As (former) Oakland A's fans, watching our team face both the White Sox and Cubs offered a bittersweet taste of America's pastime in two of its most historic venues. The energy at both ballparks showed us why Chicago's baseball culture remains unmatched, even when the games break your heart.
The Art Institute of Chicago deserves its reputation as a world-class museum, but we discovered that Chicago's real art scene thrives in neighborhoods like Pilsen. Here, vibrant murals transform city walls into an open-air gallery, telling stories of community, culture, and creativity. Walking these streets showed us a side of Chicago most visitors never see.
Millennium Park may draw crowds to Cloud Gate (aka "The Bean"), but we found unexpected magic in the quieter corners of Lincoln Park. This urban oasis provided a perfect breather between adventures, reminding us that sometimes the best travel moments happen when you slow down and watch city life unfold around you.
Speaking of slowing down, our evening at Cindy's rooftop bar delivered more than just craft cocktails. As the sun set over Millennium Park, painting the sky in hues that competed with Pilsen's murals, we understood why people fall in love with this city. The panoramic views gave us a new appreciation for Chicago's architectural heritage and lakefront beauty.
For fellow empty nesters planning their own Chicago adventure, we recommend:
Mix iconic attractions with neighborhood exploration
Don't skip the Art Institute, but save time for street art
Experience both Cubs and White Sox culture if you can
Find rooftop venues for unique city perspectives
Allow time for spontaneous discoveries in parks and neighborhoods
Chicago showed us that midlife travel isn't about checking off tourist sites – it's about experiencing places deeply and authentically. Whether you're an art enthusiast, sports fan, or urban explorer, Chicago's layers unfold best when you venture beyond the obvious attractions.
Join us as we discover the many faces of Chicago, from heartbreaking baseball moments to hidden artistic treasures!