
I am originally from the Chicago area – my parent's still live there – and I am frequently there for visits.
I love Chicago.
The city is big and as with any big city you have access to: art, food, nightlife, shopping, or whatever else you are into.
While the city is not exactly cheap – what big city is – O is so fun. The people are friendly and once you get to know the city you will realize that there are very cool neighborhoods with their own unique identity.
People have told me that they didn't realize Chicago was full of music. But the music scene there is fantastic.
And they have the best art/science museums in the area.
If you want something a little different check out China town for some good ethnic food.
Compared with big cities on the coasts you can get a lot of done fairly cheaply. Though not cheap.

When I was working on getting into a better routine I read that it takes two full weeks for us to reset our sleep schedule. Then you need to work another week, so 21 days, before it becomes an actual habit. Otherwise you can easily drop it again.
My caffeine rule is not negotiable. For me I react really pretty sensitively to caffeine. But I guess it depends on the person. If you can sleep fine with a cup of tea or coffee in the afternoon it probably isn’t a big deal.
Also I skip screen time. Artificial blue light stimulates you as if it was a bright day and slows down melatonin secretion. For me this is worse than caffeine!