Hi all, new Chicago transplant - wanted to get some opinions. What were your first years in the city like? Do you regret moving here? Are you planning to move out or do you see yourself staying long term?

Came here 20 years ago for school. Loved it in my 20s and 30s, couldn’t ask for a better balance of big city and relative affordability. Generally I found people a bit nicer than other big cities. That being said now that I’m moving into full adulthood 40 I’m ready to move on. The less you utilize the going out aspects of Chicago, the more the poor leadership, infrastructure problems, crime, taxes, and weather become unappealing.

I was born and raised in South Florida and moved for school. I was instantaneously captivated. Every single time (and to this day) I was in a cab on the way to the airport to head home for whichever break, I’d stare out the window at all the big buildings, the water, the different colored people, all the languages I’d hear, the city lights… and become totally lost in it all. There is no better feeling in the world to me. I wish you all the luck in the world in finding “your place!”

Lived in Chicago/Chicagoland my entire life and I love it here. Yeah it's got leadership issues, but rent is relatively cheap compared to other major cities, food is the best, and summertime is unmatched

For context, I've lived all over the US, Europe, and MENA for a variety of reasons (family, work,school). I moved to Chicago for grad school, and after a brief stint elsewhere for post-grad work, I eagerly moved back. It's my fave US city, and I see myself staying here for the long term.
My first few years required an adjustment to the cold, but I stocked up on Northface and learned which streets turn into windtunnels in the winter. I also found people to be quite friendly. I met several people by sitting at bars and striking up conversations on anything from sports to family.
It's more affordable than many other cities with the same features (great restaurants, lakefront, theater district, parks, sports teams, etc). I continue to be amazed at how much less I pay for things versus my years in Cali, DC, or NYC.
Transit is fantastic; I haven't had a car in years and don't see myself needing one unless I move to the suburbs or start a family.
I alos found that many people oversimplify and exaggerate the crime narrative for political talking points; if you pay attention, shootings are highly concentrated in specific areas and usually have specific targets. If you have solid street smarts, you're in no more danger than you are in any other major city.

Been here 10 years post grad. Don’t regret a thing. Been in Lincoln Park/lake view the whole time. Decent rent. Food is incredible. Summer is the best. Something to do/see/eat every weekend. So many iconic places to visit and experience in this city. I will be very sad if I ever leave.

Chicago is unmatched except for the pockets of crime/poverty/homeless — which is a problem with every major city and our rent is still relatively cheap — and the weather blows outside of a heavenly summer.

I wish we could take everything we got and give us California weather. It’s not as brutal here as a lot of Midwest states where I grew up (like MN), but life is so short in general, and I’m finding it sillier and sillier we choose to cut off access to a comfortable outdoors for half the year. Idk.

Note: I have a condition called Raynaud’s which makes my feet physically hurt nonstop when the temperature dips, so I’m particularly grumpy about this point.

Chicago is what you make it! People who like to fill their perspective with negative thoughts will think negatively about the city. They will cry about the crime, taxes, the cold, you name it. The truth is the crime is on par for any major US city, taxes are everywhere, and they need to grow up when it comes to the weather (among other things) I would say welcome to chicago! Grab this city by the horns but not the Bulls because they suck and have fun. You will meet incredible people and find your crew who will be lifelong friends. Welcome and best of luck

I regret moving here and I plan on leaving as soon as I can convince my wife Chicago is a bad place to live.

I moved here 5 years ago and I’ll never leave. Chicago has something for everyone (unless you absolutely cannot stand the cold). My only regret is living in the northern neighborhoods for as long as I did. Moved further into the city and I love it!

I regret living here since next week is gonna be bad. Fuck the negative -75

I moved here 7 years ago and love it. I won’t move unless shoved out.

Moved here 10 years ago from Michigan. Its a great city if you are into city living. It was fun for me in my 20s. I'm 34 now and have had enough and can't stand it here. Traffic, people, taxes, hate it.

I've been here since 2018 - I first moved to the Gold Coast, then the West Loop, but I am now a homeowner in Andersonville - my first few years in the city were super fun until COVID hit. The rioting in 2020 + my need for a better WFH setup caused me to move further north, but I spend a lot of time downtown.

Despite the terrible winter weather, the wrong leadership, and the high taxes, my partner and I adore Chicago. He moved here from SF, and his taxes + rent are significantly cheaper than what he was paying in California. I don't think we plan on moving anytime soon, at least for the next five years.

I grew up in Houston, and every time I return, I'm thankful I left. I'm relieved that I don't need a car here in Chicago (despite the declining quality of the CTA, it still does what it needs to do), and the food/architecture/culture is on par with NYC or London, with much better prices. Houston is a giant, hot, ugly parking lot with no zoning laws and even worse politics than Chicago. The property taxes + sales taxes are insanely high to compensate for the lack of state income tax. You complain about winters in Chicago, but the 2021 deep freeze across the South sealed my decision to never, ever go back to Texas.

My advice? Get out of the fancy downtown neighborhoods and explore other areas. Start hanging out with other Chicagoans who've been here for a long time and develop a sense of true community.

Love it here.

Born and raised in DFW, wouldn't go back. I want to raise a family in Chicagoland. I plan to go abroad but I'll be back

Been in Chicago for over 20 years and will always have a home here. Love the diversity, culture and food. I like urban living, NY was not for me, so Chicago it is!

Beem here for 5 years, I love it, bought an apartment in West Town. I don't think this will be my forever home, but I'll be here for another 5 years at least.

NYC transplant living here for 15+ years since after undergrad. I'm definitely not one of those "OMG NYC IS SOOO MUCH BETTER" people so I like to think I can be objective. Started raising two small kids in the city, but moving back to the NYC area soon family reasons. We would have stayed in the area were it not for family. No regrets spending those years here at all. You get all the benefits of a real big city for a fraction of the cost of any comparably sized city. The fact that you can live comfortably without pissing away more than half your income just on housing is huge. Weather sometimes sucks, the bloated government sucks, and being surrounded by states where anyone with a pulse can get a gun kinda sucks. But still, I think it's a great place overall, and if you really want to, you can get away from all the bad stuff you hear on the news--which I think can be overblown and is largely a perception thing because information just travels faster now than it ever has in the past--by moving to many of the nice surrounding suburbs. Those suburbs aren't cheap, but again you get more for your dollar than in comparable suburbs around coastal cities.

Chicago kicks ass, best in the spring to Fall but still great

Moved here 17 years ago. Lived on the far north side the whole time. There’s no place I would have rather have spent my 20s. As others have noted, the city has something for everyone. Most Saturday nights, I’m deciding between multiple events with friends (as opposed to being bored).

The city has certainly changed in the past 5 years or so and I’ve gotten older (and thus have less patience for traffic and the winters) so it might be time for a change. But regardless of whether I stay, I have absolutely zero regrets for moving here to start my adult life.

Moved here in 2019 and then thought about leaving a lot when my girlfriend and I were long distance during the pandemic. Harsh lock down ended, she moved out here and we've been thrilled ever since. We love the food, the live performances, the sports, the bars, just walking around and looking at buildings. I don't know if I'll spend the rest of my life here (HCOL for raising a family, crime, infrastructure) but I don't have any desire to leave before I have a kid.