The closest thing to Rockefeller Center in Chicago is the Buliding formerly known as Hancock and the Watertower areas. You have a big building with a viewing deck, smallish plaza that gets holiday decorations in front, there's high-end shopping surrounding it, a noble church across from it, and around the corner a public plaza that attracts a lot of tourists.
The Loop, remember, is the Central Business District, with especially the Lasalle Corridor being like Downtown Manhattan. North Michigan Ave is more like Midtown on the 5th Avenue side of things, with Hancock functioning a bit like a mix of Rockefeller and the Empire State building.
Times Square and the immediately surrounding blocks have tourists more or less 24/7, but other than that there's really only pockets of late-night entertainment and food scattered across NYC. Plenty of other parts of New York close up by 11 or even earlier, just like Chicago.
I don't think the Loop will ever be 24/7, and only partly because I don't think it'll get the development needed. There concept of a 24/7 city had nothing to do with 24-hour entertainment originally, and everything to do with industrialization leading to factories that were only efficient if they ran 24/7, and there was a time where there were so many factories running 24/7 that businesses sprung up to meet the needs of the shift workers, so ran 24/7. That's where 24/7 diners came up - prior to that 24/7 diners were really only along highways to serve teamsters and other long-distance travelers.
Today's concept of 24/7 entertainment really only exists in, maybe, a few dozen places in the entire globe. Most cities don't have even a single district that has 24/7 entertainment. A few might have a few clubs in close proximity that run all weekend. Even London's famous club districts aren't really 24/7, they're more like 24/3 or 24/4. Madrid and Barcelona are famous for their night cultures, but they're really just time-shifted to start and end later, they're not really 24/7.
So I don't think Chicago is likely to ever have a 24/7 entertainment district. There just isn't the demand for such a thing. A few of the megacities have districts like that, and a few of the current manufacturing hubs have districts like that supported entirely by shift workers. But the numbers of humans willing to live a true 24/7 lifestyle is just too low in most places to support such a thing. The vast majority of people over 30 or under 16 keep schedules that align with the sun. And there are only so many 16-29 year olds with no responsibilities, or with goals that allow a 24/7 lifestyle to go around.
I don't see it as a loss to not have a 24/7 district. As removed as we may often feel from nature, we are still part of it and it still largely governs how we live.
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