Chicago
July – September
Chicago has always been a city that intrigued me. As an extrovert who loves the buzz of city life, riding the “L” into downtown for an adventure felt like bucket list material. I had never been to Chicago, nor did I know anyone with roots in the city—so my imagination was my main source of excitement.
We arrived in late July and stayed through late August. The city was alive with summertime energy: festivals, tourists, music in the streets, and that infectious feeling of a city in full swing.
Staying in Pilsen
Our home base was Pilsen, a neighborhood near downtown that reminded me a lot of Boyle Heights in Los Angeles. The pink line was a quick 9-minute walk from our apartment, giving us easy access to the rest of the city. The block itself was quiet—our cul-de-sac was tucked next to an elementary school, so car noise was minimal.
Like many city neighborhoods, Pilsen is going through gentrification. At times, there was an unwelcoming vibe if you didn’t look like you were “from” the area, and I had a few moments where I definitely felt that. Still, on the whole, I generally felt comfortable. That’s one of the quirks of living nomadically—you never fully know a neighborhood until you’re there, and the internet rarely conveys the lived reality on the ground.
Favorites in Pilsen: Cafe Jumping Bean, Sleepwalk Cafe, 18th Street shops, speakeasies, the neighborhood’s street art, and of course the pink line’s proximity.
Favorite Chicago Moments
- Riding the train into downtown for climbing sessions at First Ascent
- Catching a Cubs game at Wrigley Field
- Relaxing at North Shore Beach Park
- Wandering the Riverwalk and marveling at Chicago’s architecture
- Taking the (slightly cheesy but very fun) architecture boat tour
- Chicago-style hot dogs, local breweries, and some incredible Mexican food in our neighborhood
- Fiesta Del Sol festival in Pilsen
- Exploring Irish pubs, seeing shows at iO Theatre, and live music venues across town
- Visiting the Griffin Science Museum
- Eating Sharpie’s Pizza
- Spotting Lollapalooza attendees flood the trains in waves of neon and glitter
Chicago delivered on all the things it’s famous for—transit, food, culture, and walkability. But when I thought about it as a place to live, it didn’t climb high on my personal list. The lack of quick access to nature was the biggest drawback for me. Cities like Portland, OR, or St. Pete, FL, felt better balanced with both vibrant city life and easy escapes into the outdoors. Still, Chicago left a strong impression, and I can see why so many people fall in love with it.
Green Bay
Green Bay has always been part of my imagination thanks to my dad, who frequently visited as a kid to see his cousins. He’d tell stories about camping, adventures in Door County, and family fun that made the area feel legendary to me. Still, I expected it to feel quiet or suburban (and at first, it did)—but once we settled in and started doing the nature-filled activities we love, I understood exactly why people adore Green Bay.
The weather played a big role in shaping my experience. Chicago had been brutally hot and humid, while Green Bay welcomed us with perfect late-summer days in the low 70s and crisp, cloudless skies.
Packers Country
We happened to arrive just as the Packers’ season was kicking off. The whole city buzzed with energy, and we were lucky enough to attend the second game of the season (Packers vs. Washington Commanders). My dad’s cousin John has season tickets and graciously let us use them while he was out of town. He even has a house across from the stadium that he uses for tailgates—on game day, the whole neighborhood came alive with cheesehead hats, green and gold jerseys, smoky joe’s grilling hotdogs and burgers, and the unmistakable joy of a football town rallying around its team.
Staying in Astor Park
Our neighborhood, Astor Park, was a charming historic district along the Fox River, with homes dating back to the 19th and early 20th centuries. The slow pace, walkability, and friendly neighbors made it easy to settle in.
Local Favorites:
- Lox Stock and Bagel for breakfast
- St. Brennan’s Irish pub for Guinness
- The Lorelei Inn
- Studio 1212 wine bar on the river
Favorite Green Bay Adventures
- Exploring Door County: hiking Peninsula State Park, hiking Cave Point county park, strolling through Fish Creek and Egg Harbor, and eating fresh seafood at local restaurants
- Rock climbing at Odyssey Climbing Gyms
- Hiking Hill Cliff State Park
- Walking the Fox River trail to Studio 1212 for wine and snacks
- Evenings spent with Paloma and a perfectly poured Guiness at cozy neighborhood pubs
A Perfect Send-Off
On our last day before heading to Minneapolis, my dad’s relatives gave us the full Green Bay experience. We started with an early morning hike at Peninsula State Park, had lunch in Fish Creek, and then spent the afternoon on a boat ride across Green Bay, hopping between harbors and islands. It was a perfect goodbye—and a reminder of how family can transform a place into something even more meaningful.
Reflections
Part one of our Midwest journey has been eye-opening. I hadn’t spent much time here before, and my curiosity was fueled mostly by stories and stereotypes. Experiencing it firsthand in the summer showed me how special this region is: friendly people, a slower pace, and a deep sense of pride in community and place. Next stop is Minneapolis followed by a short stint in the Ozarks on the way back south for the winter.
Chicago gave me the thrill of big-city living, while Green Bay reminded me of the joy of family, nature, and tradition. I can’t wait to see what Minneapolis has in store.
-RoamingRushka
RoamingRushka 
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