Should You Move to Chicago?
Insights and reflections from people who've done it: American edition.
As we near the end of the Should You Move project, it would be fun to do something completely different. This time, it’s a group project, with Italians moving to America instead of the other way around—with fascinating insights into each country's differences.
Meet the Cool Beans Expat Club!
The group formed when four Italian women moved to Chicago. Faced with isolation and culture shock, they decided to do something about it. What began as casual coffees and meetups quickly blossomed into a lifeline: dinners and larger events to create an international community and combat loneliness. Honestly, nothing is more Italian than creating community through food and conversation.
If you caught my chat with Beth Le Manach of Entertaining with Beth on Finding Home, you’ll discover a common thread connecting many thriving transplants: you’ve got to put yourself out there—even when it’s hard (and it always is) if you’re going to be happy in your new home. The success stories of the Cool Beans' women prove the power of a positive mindset and community over fear and isolation. La Dolce Vita in Chicago, baby!
The Cool Beans Expat Club, Chicago
1. Background:
Country of origin: Italy
Country of current residence: United States
Length of time living abroad: from 1 year to 10 years among the 4 of us 2.
2. Motivation:
What was the primary reason for your move? (e.g., work, study, retirement, lifestyle).
Mainly, we all moved for work.
3. Practicalities:
How challenging was the visa and work permit process?
It really varies from case to case. Some of us had extremely frustrating experiences, especially when renewing our work visas—even working for large multinational companies, we received poor legal advice that led to unnecessary travel restrictions, preventing us from attending important family and friend events. At times, the process was so stressful and emotionally draining that we genuinely considered leaving the U.S. for good.
What were the biggest hurdles in setting up your life abroad (e.g., housing, healthcare, banking)?
One of the biggest challenges was navigating the banking system. Without a credit score, it’s nearly impossible to do anything—rent an apartment, get a loan, or even buy a property. But how can you have a credit score if you’ve just arrived in the country? It’s a frustrating cycle that every newcomer has to go through.
The financial culture here is also very different from what we’re used to. The reliance on credit cards means many people spend beyond their means, often living paycheck to paycheck simply because they have credit available. This mindset was a big adjustment for us.
Finding an apartment in a major U.S. city can be tough, but compared to Italy and much of Europe, it’s still more accessible. In Italy, housing is extremely expensive relative to salaries, making homeownership nearly impossible for many. It’s not uncommon for Italians to still live with their parents well into their 40s because rent is unaffordable. Meanwhile, Italy is increasingly catering to wealthy tourists rather than its own residents.
Healthcare, however, has been the most confusing and frustrating adjustment. The system feels designed to benefit insurance companies rather than patients. Finding a trustworthy doctor is difficult, and you’re never sure if medical recommendations are genuinely in your best interest or just a way to bill your insurance. For Europeans, the lack of price transparency is shocking—you never really know how much you’ll pay until you get the bill. A routine blood test that costs around $50 in Italy can cost hundreds of dollars in the U.S., even with insurance. Understanding and navigating the system has been one of the most stressful parts of living here.
4. Cultural Adaptation:
What were the most significant cultural adjustments you had to make?
One of the hardest cultural shifts for us was how friendships are formed. In the U.S., people often say, “Let’s stay in touch,” but follow-through is rare, making connections less consistent and spontaneous. Even among Americans, friendships seem more scheduled than organic, whereas, in Italy, you’re naturally welcomed into existing circles.
We also had to adjust to certain social norms—like avoiding deep conversations about politics, religion, or personal struggles. Vulnerability is key to meaningful relationships, but conversations often stay light here.
Similarly, the culture of exaggerated positivity was new to us; in Italy, feedback is blunt, whereas, in the U.S., even minimal effort is met with enthusiastic praise.
Dining out was another major shift. Restaurants close early, and we had to get used to eating dinner much earlier than we would in Italy. We also found it frustrating that servers constantly check in and bring the check without being asked—it can feel like they’re rushing you out.
All that said, some aspects of American culture resonate with us. We love the freedom of self-expression and the variety of experiences available in big cities like Chicago.
How did you handle language barriers and cultural misunderstandings?
The article we published on April 1st explained this very well! Great timing!
5. Quality of Life:
How would you rate your overall quality of life compared to Italy?
Both have pros and cons. Italy is incredibly bureaucratic, slow, and often frustrating. The job market is complicated, with too many contract types—many of them short-term—making it hard for the younger generation to become financially independent and move out of their parents' homes.
On the other hand, we deeply miss the quality of life in Italy. We miss walking or biking everywhere, grabbing a quick espresso at the bar, the incredible food quality, and the sheer variety of fresh produce (in Italy, we have so many different greens!). In a way, it feels like a trade-off between accessibility and quality—while life in the U.S. is often more efficient, Italy offers a richness of everyday experiences that’s hard to replicate.
6. Professional Experience:
How has living abroad impacted your career? Were you able to find employment easily?
Since we moved primarily for work, relocating abroad significantly impacted our careers. The job market in Italy is incredibly stagnant, with limited opportunities for growth and recognition. One of us left because the company she worked for offered little to no career progression and was run in a typical “Italian” way—people yelling in the office, no meritocracy, and a lack of strong structure or global vision. In contrast, the U.S. job market is far more dynamic. The emphasis on meritocracy has been refreshing—hard work is actually rewarded, and career growth feels attainable, unlike in Italy, where middle management rarely changes and advancement is slow; here, talent and effort open doors. While adjusting to a new work culture came with its challenges, the professional opportunities we’ve found have made the move worthwhile.
7. Advice for Future Expats:
What advice would you give to someone considering a similar move?
One thing we’ve all learned is that while moving abroad sounds exciting, it can also be incredibly lonely. The reality of being in a new country hits hard—like the first time one of us arrived in Paris, walked into a supermarket, and felt completely out of place. That day ended in hours of tears and self-doubt. Over time, things do get better, but not because the country changes—it’s because you start building your community.
The biggest lesson? Home isn’t a place; it’s the people you surround yourself with. There’s no perfect country or ideal destination— the relationships you form make the difference. So our advice is simple: be open-minded. Say yes to invitations, go to events, and push yourself out of your comfort zone. It might sound like a cliché, but it’s absolutely true. The more you put yourself out there, the faster you’ll find your people—and that’s what will make any place feel like home. This is why we founded Cool Beans Expat Club, as it’s difficult to make friends in a new country, especially in a country like the U.S. where people are more isolated than ever, especially after Covid, and the trend is not reverting.
8. Overall Experience:
Looking back, would you say moving abroad was a positive experience? Why or why not?
Absolutely, YES. We first realized the importance of stepping out of our habits at university when we met international students. Even then, it opened our minds in ways we hadn’t expected. Living abroad amplifies that feeling a thousand times over—it pushes you to evolve to become more aware of yourself and the world around you. We’ve seen so many people who never left their hometowns, believing that’s all there is. But the moment you step outside that bubble, you realize how small your world was and how much more there is to discover. Moving abroad isn’t just about changing locations—it’s about expanding your perspective, challenging your assumptions, and growing in ways you never imagined.
 | A guest post by
|
So interesting to read about the cultural differences, I can only imagine what a shock it would be for Italians to get the check before they are finished their meal! I always found it quite rude and confronting as well.
Do you think you'll stay in Chicago? Or do you plan to move back to Italy?
Great post and this was fun seeing things from a different perspective. I can totally understand that positivity thing, it can be overbearing in the US, although it's a little different in Boston, where I lived for 8 years. They're a little less enthusiastic in the northeast.
I can imagine that healthcare would be the biggest shock and toughest adjustment. If you've got good insurance, great. Otherwise...yikes.
The bureaucracy, on the other hand - I hear you. Although I think Italy is probably worse (?) than Austria with this, it's incredibly frustrating to deal with. Hell, in Ukraine it was far easier and they still have all sorts of Soviet-era bureaucracy to get out of the system.