Should I move to Chicago?

Okay. So I accepted an analyst role at an IB headquartered in Chicago but I do not know much about the city. I am originally from Boston and go to college in Boston so it would be completely new surroundings for me.

Is Chicago really as unsafe as the media portrays it to be? I've read that over a 1000 officers in the police force are going to resign over the next few months over vaccine mandates... That doesn't bode well for already rising crime in the city. What neighborhoods are safe to live in?

I visited Chicago briefly a couple months ago and the city seemed very professional - everything seemed dead after 7pm (at least downtown). Furthermore, it seemed like everywhere I went, all the people I was surrounded by were at least in their 30s and 40s. Where do all the young people live and where are all the fun spots?

Lastly, is it true that once you work in Chicago, it can be easy to get stuck in the midwest? Do exit ops into PE/VC only exist in the Chicago area for Chicago IB analysts? If I wanted to have an exit op in Boston or NYC, should I try to move to one of my firm's offices in those locations instead?

Any Chicagoans or those who have worked IB in Chicago please share your insight! Any tips or advice about living in Chicago would be much appreciated. Thanks!!

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Comments (16)

Nov 23, 2021 - 3:08am

As someone who is from Chicago but works in NY, here are my thoughts:


- Cost of living is a fraction of NY/SF and considerably lower than Boston. Don't underestimate this. I make more than most of my friends still in Chicago and they all have nicer apartments than mine in NY

- people are generally pretty friendly compared to the east coast

- great bars/restaurants/sports

- Summer in Chicago is truly second to none. There are things happening every weekend, and the whole city comes out to play for 3 months


- The winter is cold and long, even compared to NY or Boston. In January, it's not uncommon to stay below freezing for weeks at a time, with a few sub-zero days sprinkled in

- It's fairly isolated. I don't think people talk about this enough, but you can't really drive anywhere interesting for a weekend trip like you can on the coasts. Lots of cornfields.

I think it's a great city and in my opinion, the amazing summers more than make up for the tough winters. As for crime, yes, there are some neighborhoods that are essentially war zones, but those are on the far west/south sides so you would have to purposely go way out of your way to get there. It's sad, but almost all of the violent crime you read about happens there, so most of the city is actually pretty safe. A lot of young people live in Old Town / Lincoln Park / Lakeview. Basically anything north of the river should be safe, with lots of fun bars and restaurants.

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Nov 23, 2021 - 6:31pm

Made the move having it not be my home a few years ago now. Happy to share a few thoughts for you. 

- The loop (downtown) is dead after work. Don't live there and normally unless you are having happy hours (or seeing a show or something) you won't spend much time there aside from work. It's gotten worse after COVID, with workers not coming back, but you won't really spend a ton of time there outside of in an office. 

- River north is where a lot of young people are (immediately above the loop, across the river - aptly named!). It's a ton of bars, restaurants, etc. Many luxury buildings here, a lot of people leave college and spend a few years partying there. Others are Wrigleyville (CTA Red line north - call it 20-25 minutes from the loop give or take) and then I've heard more people headed to Lincoln Park and/or Lakeview area as well since you get a few months of glory near the lake. West loop has younger folks as well - but it's more dominated by DINK's and/or those that just had kids. West loop also had a ton of great bars/restaurants as well - a lot of big named ones there as well. Some people live in Streeterville - Gold Coast is predominantly older money. 

- Some other neighborhoods are Ukrainian Village and then Wicker Park. Those are a bit more north west-ish of the Loop. If you follow the blue line out you end up with a bunch of places that are pretty cool where people live as well (younger too, some older) it's a mix. Any of these I mentioned are generally safe - with my preference being living further east to the City, or Northward of the city towards the lake at this point. 

- Crime wise... I'll be honest. I'm leaving the West Loop as, in my opinion, it's getting a bit sketchier and murders are increasing on Randolph (where a lot of the nice places are to eat) and crime generally is moving east from the United Center area into what has been built up over the last 10+ years. It's not unsafe - I just wouldn't go too close to ashland late at night as a reference point. Most areas, generally, are not the murder capital you see on TV. That's largely in the south and west - it's a very serious problem. My biggest issue long term in Chicago is the inept leadership that continues to enable crime, hilariously bad budget deficits, terrible spending policies and taxes that will certainly be going upward.

- That being said - I have grown to enjoy Chicago. It's a great city and there is tons to do. No shortage of interesting things to see, sports to play, etc. The winters suck - no way around that. The lake is generally worth the trade off in most years - unless it's in the negatives for a few weeks, that's when you get on a plane and get the hell out. 

- Flying is actually decent, given the location of Chicago you have access to a lot of places with relatively short flights. O'Hare is a beast in the winter, but as I've said before originating isn't as bad as connecting through IMO. 

- There is a pretty big investment community here. It may not be as robust or focused as others, but plenty of jobs and opportunities should you want them. 

I could keep going - but some thoughts. Happy to shed light on anything else. I've enjoyed my time in Chicago - will I be here in five years? Who knows but I wouldn't be mad if I still were. 

Nov 28, 2021 - 11:17am

Chicago is the one city I ever lived in where the local politics actually would impact my mood on a semi regular basis. The corruption , waste, and incompetencey is astounding 

that said it's a very magical place. North side (old town to wrigleyville) is a great place to live, meet people, and basically an extension of college. You get A tier city living with a fraction of the price of a New York or LA

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Nov 25, 2021 - 11:42am

I lived in Chicago for 5 years (2016 to 2021). I would recommend living in River North/Gold Coast or if you want to live further north of downtown check out Lincoln Park/Lakeview.

Nov 28, 2021 - 1:00am

Chicago is similar to using the Infinite Money Hack in Grand Theft Auto. Basically, $1 earned in chicago is equal to $17 earned in NYC or SF. So if you Make $100k in Chicago, it's basically the same as making $1.7 million in NYC.

So when doing the math on your new opportunity, be sure to multiply your Chicago salary by 17 to figure out what the NYC equivalent of that salary is.

Nov 28, 2021 - 1:25am

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