I ran it for most of 2020 before moving to KDE. I hadn't looked at the project recently until today and saw that it now has 'Chicago95 Plus! A tool to preview and install Windows 95/98/ME/XP themes'.. I'm going to have to try it that out. Of course, I'm probably an outlier in that I love the visual design of user interfaces from that bygone era.

I used XFCE with this exact theme for a few months and I loved it. The only thing I didn't like was that the light gray top "outline part" of the window decoration doesn't disappear when you maximize a window. I never figured out how to fix that.

I've used Memphis98 (similar to Chicago95) since it came out. Although just as a GTK-theme, not the entire desktop. Window manager is FVWM and taskbar/panel/session-manager is LXQt, so it's a bit of a Franken-desktop :)

For Qt-apps I use the "Windows" style so they fit together nicely.

Comparing Memphis and Chicago, there are some layout-bugs in Memphis, but I feel like it's overall a bit better balanced than Chicago.

I think all new themes are too bright and flat, Windows 9X was perfect (at least in that regard).

My grandmother's computer is an old Debian box with nothing more than `ly` (as a DM), xfce, Chicago95, and Firefox. She loves it, though I made a ton of tweaks here and there to make it easier for her to use (specifically a ton of website launchers on her desktop). She got lost in regards to how to use her computer back in the XP>8 transition so it was great to be able to bring her back to that style of desktop and have the system be easier to fix than Windows 8 or 10.

I’ve used chicago95 as a daily driver for a few years now. It’s simple, high contrast, gets out of my way and lets me work.

rock solid lately. also on par with XFCE in terms of resource usage, yet lot and lots more features.