Living in Chicago as Expat: Things to Know

Are you thinking about living in Chicago?

In this Expat Interview, Federica shares her expat life in Chicago, United States. She includes her moving procedure from Italy, the cost of living in Chicago, the good and bad things about Chicago, and more.

About Chicago

Often considered the third city, after NY and LA, Chicago has all of the ingredients of a beautiful American city.

There are fabulous parks, museums and restaurants, world-class skyscrapers, entertainment, and even a Great Lake with beaches.

Built on a grid system, with Lake Michigan set as the natural border to the east, the Windy City (to use one of Chicago’s better-known nicknames) is a favorite destination for many.

Travelers visit this metropolis to discover beautiful architecture and eateries.

expat moving to Chicago

Why did you move to Chicago?

My move to Chicago is also the love story that has changed my life.

I was dating Mr. P. on a long-distance relationship within Italian boundaries. After a beautiful holiday in Thailand, he called me one day, announcing that he had received a job promotion.

Good news! I thought before even knowing that he should have moved to Chicago. We spent the entire following weekend thinking about our future, and we were on the edge of breaking up until I decided to move with him to America.

How to prepare for moving to Chicago?

Moving to Chicago was not easy.

I had my job in Italy, and even if I were dating Andrea for two years, it would have been our first experience as a full-time couple.

I was scared that sharing our daily routine could have destroyed our balance as the couple used to be a long-distance liaison. Because of this uncertainty, I didn’t want to quit my job.

Luckily, I asked for and obtained from my company a sabbatical year. The other most significant problem was the one related to my Visa.

At the time of our move, Mr. P. had a green card (a permanent permit to live in the US), while I arrived in Chicago with a touristic VISA only valid for no longer than six months stay.

Going back and forth with Italy was too risky, and the border already blocked me twice, letting me understand that I should have applied for a long-term visa.

That’s why after five weeks in the US, I came back to Italy, and I applied for and obtained a student Visa.

In the meantime, I searched for schools since my final goal was to spend my American years studying for a master’s degree.


  • Moving tips: Relocating abroad? Try Sirelo for free quotes from top international movers that fit your budget. Learn more here.
  • Money transfer: I use Wise for my international transfers. Quick, secure, and their fees? Way lower than most banks I’ve tried!
  • Expat insurance: Life abroad has its surprises; make sure you’re covered with expat insurance.

What is the cost of living in Chicago?

a. Taxes

Coming from Rome, the capital of Italy, I found Chicago slightly cheaper than my hometown regarding taxes. However, I am aware that Chicago ranks among the most expensive cities in the US for American standards, with taxes over 10%.

It was tricky at the beginning to remember that to the prices on every kind of goodies, I had to add taxes, but after a while, I got used to the system.

b. Transportation

Before moving to Chicago, I drove my car daily from and to my office, and the commute was stressful.

It is the reason why when I moved, and I pleased Andrea to search for a place downtown. I decided that I would never have to retake the car. And so I did during my Chicagoan years.

Of course, the real estate market is more expansive downtown, but I also looked for the safest area to move in and enjoy my new life as a pedestrian.

c. Apartment in Chicago

We found that buying a place would have been a good investment regarding the real estate market.

Also, taking advantage of the exchange rates, it was even cheaper than renting, and after a monthly search, we bought an apartment in September.

d. Entertainment and food

Chicago has excellent offers of entertainment, and many festivals are beautiful and free for residents.

Like other big cities, the dining scene is vibrant and with a full spectrum of options, from street food to some of the best restaurants in the world.

cost of living in Chicago

How to deal with difficulties when first moving to Chicago?

Chicagoans and Midwestern, in general, are very friendly, and it was truly easy to overcome all the first-time difficulties thanks to their kindness.

Even if when I moved, my English wasn’t perfect. From the porters in my building to the people I stopped in the middle of streets asking for directions, everybody spent a lot of time understanding my requests and making sure I would have found the answer I was looking for.

Moving to Chicago has been my first international move, but not the last.

I can easily say that moving abroad is always tricky concerning culture shock. The fact that Americans had to hide alcohol when bringing it from one place to another was so unusual to me coming from Italy, that I was shocked. And like this little thing to many others, I was staring at these differences in the beginning.

It was also shocking the loud volume of the city. I have never liked the too loud sirens of ambulances and firefighters.

As time passed, I got used to them, and I experienced a culture shock the first time I came back to Italy after three years!

Did you experience any discrimination in Chicago?

Chicago has been one of the most welcoming cities among all the places I have been as a tourist and an expat.

People are genuinely kind, and it is effortless to interact with them. They made everything they could to help me and make me feel at home.

I felt very welcomed as part of their community, and I have never faced any problem as a foreigner.

How to overcome culture shock while moving to the United States?

When I moved to Chicago, I had tons of small cultural shocks.

One was related to food. Whenever I entered a grocery store, I stared at the large dimensions of fruits and vegetables and poultry and meat.

I was scared of the American use of chemicals and hormones to feed animals. To overcome my fear of eating unhealthy food, I changed my shopping habits and transformed my life into organic.

The second biggest shock regarded friendship. Contrary to Italian people, Americans tend to move many times in their lives and to stay less attached to people. Italian people are led to a less nomadic life that brings them to stay connected to the same social group for their entire life!

In the beginning, I was shocked by the considerable flexibility of Americans with connections. Still, when I understood the social reason behind this way of befriending, I accepted it and lived happily with American pals.

What do you like about Chicago?

I love summertime in Chicago when the city flourishes.

Sipping a drink on a rooftop bar or heading for a picnic in a park while listening to a beautiful concert is a delightful experience.

I love the beautiful beaches on the lake and the daily festive atmosphere in this season of the year.

expat living in Chicago moving to United states
Chicago from the lake

As a mother of two (born in Chicago!), I have to say that it is also a very child-friendly city.

Restaurants are big enough to welcome parties of several families with young kids, and there are many activities and classes for children of different ages.

Are there bad things about Chicago?

On the negative side, one thing is an absolute nightmare: the cold winter, which sometimes lasts nine months. It is brutal, and it is tough to cope with.

My tip was to leave Chicago for a warm destination every 40 days. The good thing is that Florida is at a 2 hours flight distance and Puerto Rico at 4 hours!

What are your favorite things to do in Chicago?

I love going out for dinner with friends and trying new restaurants. The dining scene is exciting, and new eateries options open very frequently.

The concert season of the Symphonic Orchestra presents high-quality programs.

When I was alone, I used to escape as much as possible to the Art Institute. This is the best escape Chicago can offer for an art lover like me.

Where do you recommend visiting in Chicago?

I love the beautiful architecture realized by great firms. Mies van der Rohe and Frank Lloyd Wright are just two of the most famous architects that designed important buildings in and around the city.

An experience I highly recommend is taking a boat ride with the Chicago Architecture Foundation and exploring the city from the river.

Or, if you are not familiar with America, you should go south and visit the historic campus of the University of Chicago.

places to visit in Chicago
Chicago from the river is a beautiful way of discovering the city/

How to make new friends in Chicago?

a. Being a student

My first network was the one I built around the English school firsts and the graduate program then. Attending schools is the easiest way to make friendships.

I also took a watercolor class to meet ladies who share my artistic interests.

b. Through the Italian community

Another easy way to meet friends was through the Italian community.

Andrea is a member of the Accademia Della Cucina Italiana, the Academy of Italian Cuisine, a Cultural Institution of the Italian Republic since 2003.

Founded in 1953 to safeguard the traditions of Italian Cuisine, the Academy has branches around the world, and its members meet monthly at a different Italian restaurant.

Through this club, I had the opportunity to meet beautiful people I could share my language and cultural habits while away from my country of origin.

c. Through parent community

This way allows me to reach people when I become a mom.

My first daughter’s music class was where I met other lovely families that became our friends over the years.

Do you hang out with locals or foreigners mostly?

I would say 60% of international people and 40% of locals.

Where is your favorite place in Chicago to meet friends?

I love the rooftops of Cindy’s and Cerise when we are large parties, and I prefer the Shangai Terrace and NoMI when I go out with just one or two friends.

I also enjoy dining out at North Pond. To discover more about my favorite places, you can check my guide to restaurants and bars here.

Do you interact with any expat communities in Chicago?

As I mentioned, thanks to the Italian cuisine academy, I interact with the Italian community of expats and Italians living in Chicago.

Besides the Italian community, I know other foreign people through my graduate studies and my Italian friends’ studies.

A memorable experience in Chicago

I still remember my first fourth of July there. A few days after I moved there, I was so excited at the idea of watching a beautiful show of fireworks. But it was revealed to be my biggest disappointment.

things to do in Chicago

Our temporary flat was in a skyscraper, and from the window on the 83rd floor, everything looked so far away and incredibly small.

Instead of seeing spectacular fireworks displays, I was watching a show of little, colorful bubbles, like tiny blinking lights appearing and disappearing in the darkness of the night.

Did you change your perspective of Chicago after living here?

I liked Chicago as soon as I arrived but never liked some aspects of being there. I never felt in love with the weather – too cold for me- nor did I ever want the loud sirens and the acoustic pollution in general!

Besides these aspects, I loved living in a city facing a lake as big as a sea!

What are your advice and tips for moving/ living in Chicago?

If you need to move as a family, make sure that every family member has a proper Visa. To survive the brutal cold, forget fashion, and buy a snowsuit.

You might need to wear it over regular clothes during the coldest day. And buy all the equipment for wintertime there – it’s genuinely cheap compared to European prices.

Would you recommend others to live in Chicago?

Living in Chicago has been a delightful and enriching experience. I had the chance to discover and integrate with another culture, which I consider a fantastic opportunity for personal growth.

People in Chicago are so enthusiastic that their enthusiasm is now part of my way of being. Even if only for a few years, I would recommend moving to Chicago to experience Midwest at his best.

expat living in Chicago
View of Chicago from the rooftop bar of the Athletic Hotel

What have you learned from living abroad?

I lived in Chicago for four years before moving to London. For work reasons, Mr. P. has always led a nomadic life, and since I became Mrs. P. (but by chance, I was born as Miss P.!), I am living across the globe.

Living abroad was the most enriching experience of my life. No matter the country or city where I stay, I always learn something different. People across the world have their own rules and educational system, and the more I move, the more I get to know on my skin how these systems work.

It is an excellent opportunity because, at the end of every experience, I understand what I like and dislike about one system. The more I move, the more I create in my mind Utopia, an ideal place with the very best from each country I have lived in.

More about Federica

expat living in Chicago

Curious by nature and wanderer at heart, Federica is an Italian Journalist and Digital Media Storyteller. By chance, by desire, and by love, she has been leading a nomadic life since she met, almost ten years ago, Mr. P., the man she eventually married.

Travel after travel, move after move, Federica is now based in London, where she manages her travel and lifestyle blog, A stroll around the world.

You can follow her adventures on Facebook and Pinterest.

The opinions expressed here by Expatolife columnists are their own, not those of Expatolife.

Similar Posts

Leave a Reply

Your email address will not be published. Required fields are marked *