I think it's only truly dangerous if you hang out in the wrong neighborhoods.
I don't know about everyone else, but I grew up in a fairly big city. And there lots of places you could hang out and chat, and no big deal. And a few places your family and friends always told you to avoid. Drug dealer neighborhoods, or just gang territory. There are some of these in almost every big city.
So I don't think Chicago is the cesspool some people seem to think it is.
Dating in Chicago is diverse, lots of different people and nationalities. There are party animals here, but a lot of folks who are more mature and looking for something stable.
From what I can see from my backyard, there are a lot of single people here who are hard to impress.
And in a big city where there are tons of people men are always going to be competing for women's attention. On the other hand, since this is the midwest technically, I don't think it's quite as competitive as say New York.
You could use a Chicago dating app and I know Tinder,
Flure,
Adult Friend Finder, EliteSingles, and
Ashley Madison are pretty popular in the Windy City.
I would say Chicago is also not as much a transplant city as cities up north, and there might actually be more people ready to settle down here, who aren't at the first level of their new career.
In short, you do have to diversify the way you date and don't waste too much time chasing after someone who doesn't seem to like you. In a big city, there are always more options.