NYC vs Chicago: Where Should I Move?

I currently have an opportunity from my job to relocate to either NYC or Chicago from Cleveland, Now I just need to actually make a decision, but I'm really having a hard time and am looking for some input from those on here.

For background, I'm 29M and looking to live in a place that's truly walkable/bikeable/transit-oriented/etc and could ideally live without a car. I like going to bars/restaurants, concerts (especially EDM), traveling, and exploring new spots. Personality wise, I'm an introvert but also very direct and honest when talking with people. I'm also single and don't plan on having a family, so being in a place where I can meet people like that is ideal for me.

I've visited both cities multiple times and have always enjoyed my time in both, though I'll admit I like NYC a little bit more. Despite this, there are still factors I have to consider for both. For instance, while I prefer the food, transit, diversity, and walkability of NYC, it's obviously going to be a lot more expensive. On top of that, I won't know anyone in my NYC office and I'll basically on an island from the rest of my team, along with being in a more "business formal" environment at work. Chicago would be good because my money would go way further and I'd be around more of my direct co-workers and be in a more casual environment. My higher-up managers (who are in Chicago) are nudging me to go there, but always tell me it's my choice on where I'd move. I also love walking along the lake and imagine I'd be able to have more budget to travel to other places over the next several years. My big concern with Chicago is that the CTA seems to be hit or miss whenever I use it, which knocks off points when wanting to live in a transit-oriented city. Basically, I feel I'm choosing between a city I like a bit better but will cost more and may have a less ideal working environment or a city where I'd be around more of my coworkers and have more money to travel and such.

So let me ask you this: should I pick Chicago or NYC? What would you do if you were in my shoes? Are there any locals that can vouch for either place or may be able to provide any insight I may not be aware of?