Chicago or NYC?

Dramatically different cities and lifestyles. Very doubtful you will be able to get a pay increase for being New York. I’ll pro-con for you:

New York:

• very diverse and has virtually unlimited restaurants bars etc.
• Very high rent and very high cost of living (it’s not just rent it’s groceries, a beer at the bar, your gym, etc)
• High cost of living means your apartment will suck and it’s basically impossible to save
• Culture of hustling and keeping up with others. People keep up to date with the latest fashion, there’s higher drug use, more sharp elbowed people or people always competing with one another in various categories of life
• most the people around you will work in finance. There are more potential jobs out there, but also a more competitive hiring market. For every large finance firm there are a huge handful of IVY undergrads who are trying to work there and want to be in NYC
• Pressure to go out and to spend money is very high
• For dating: plenty of smart attractive people, hard to find kind people 
• city isn’t going anywhere and will likely always be booming
• people frequently leave the city during the summer and the winters aren’t too bad
• Crime isn’t much of a concern—the number of people means you can feel decently safe walking down the street at night

Chicago:

• lower cost of living, seriously everything is cheaper from rent to drinks to the gym. By my estimates being a finance bro in both cities, status quote has Chicago finance bros at 2/3 the cost and you have higher quality at every level. As an example, my finance bro friends in Chicago have 2 beds 2 baths with views of the lake and spend about $1700-$2100 a month. My finance bro friends in NYC spend $2600-3200 for a 2 bed and they share a bathroom and have no kitchen or view. A nice dinner or club in Chicago will be 2/3 the cost as well. This adds up. Also, you top out in Chicago a lot quicker. It’s hard to find a 2 bed where you will pay more than 6k a month in Chicago anywhere, in NYC there are plenty of places well north of that.
• Lack of diversity and restaurants and bars. I don’t think people feel Chicago is small, but it isn’t unlimited. You could try a new great restaurant in NYC every day and basically never run out of restaurants. In Chicago you eventually know the spots that are nice and you like after a few years.
• Culture is way more laid back. Most people don’t do finance. There isn’t sharp elbowed culture at all. There also isn’t pressure to spend money or keep up fashion wise. People wear jeans and flannels to many bars. It’s rare you find someone who knows about or cares about streetwear or fashion in general.
• dating it’s harder to find attractive smart people. Girls are bigger and both guys and girls are dumber. But almost everyone is going to be friendlier. I went on dates all the time for years and basically every person I met in Chicago was nice, just many times they were too dumb or boring to date. My friends in NYC have horror stories of guys or girls exhibiting sociopathic behavior or being so in love with themselves it’s comical.
• Less drug use, less hustle culture, less keeping up with everyone in terms of spending.
• Winters are horrible, summers amazing. People don’t like leaving in the summer because Chicago summers are incredible (you are right on the lake and the city has an air of lightness to it with plenty of space). Winters are so cold your hair will freeze if you took a shower and walk outside.
• City has depressing prospects. The state of Illinois has high taxes and a pension crisis and the recent mayor elect is anti business and was/is pro abolish the police. Wealthy people are leaving Chicago and business opportunity is worse.

My 2 cents, they are very different, but you could move to either pretty easily. If you are financially conscious, NYC is a terrible move. I think you should value Chicago versus NYC living at + 24k pretax earnings. But, you pay for that with bad winters, a suboptimal city management, and less things to see.
 

I saved basically a down payment for a house by living in Chicago from 22 to 26. My friends in NYC didn’t, but they wouldn’t trade the experience of being around the most busy city in the country for their 20s for any amount of money.