I think Chicago will really start to boom in the next few years, especially if we get leadership with some vision for the central area (promoting walkability, transit, and non-chain commercial districts). As mentioned, Chicago's got the second biggest traditional urban core in the country, but up until now, the Loop – at the center of it, of course – has only been used for weekday office hours and lunch spots. That is quickly going to change, with a new mixed-use district emerging among some of the city's best architecture and transportation access (see this:
https://chicagoyimby.com/2023/02/six...eimagined.html, also vintage office buildings in other parts of the Loop quickly pivoting to residential or mixed-use).
At the same time, much of the city's boom over the last decade has been infill in the Loop-adjacent neighborhoods – the former ring of industrial or vacant land that surrounded the Loop and Mag Mile. A lot of liminal areas and dead-feeling streets have become dense with new construction, and the streets feel noticeably busier from North to Cermak, west to Ashland.
I think the Loop's turn to mixed-use connected with the new density and momentum of the Loop-adjacent neighborhoods (West Loop, River North, Streeterville, South Loop, etc.) will make downtown feel really special. It's always had great qualities like its architecture and lakefront access, but growing up here there was a sense that it could be much more and have more energy. I think having connectivity between these neighborhoods, with walkability and a more vibrant street experience as focuses, will get it there.
Chicago's neighborhoods have always been great, and it's where Chicagoans will tell you the real heartbeat of the city is. I think that's evolving, and Chicago's downtown is finally coming into its own as a great place too – not just one that looks great, but one that feels exciting too.