It tastes like some kinda fancy herbal liqueur that someone accidentally dumped a bottle of crushed up tylenol into. It's aggressively bitter. The best description I've heard was "Well gin, with a baby asprin wrapped in grapefruit peel and rubber bands"
It's really hard to explain but as you drink it you kinda start to like it. I was given a shot by a stranger when I first visited Chicago. I wound up moving to Chicago not long after that. I was given more shots at nearby bars as a "Welcome to the neighborhood" kinda thing and I was like "noo no thanks I know this game" and drank them only to be polite.
But before I knew it, I wanted some, so I bought a bottle at the liquor store. Now I legitimately want a shot of it sometimes... over other liquors. I never feel like drinking a shot of any other hard A. When I moved here I only drank beer. Now I only drink beer and the occasional shot of malort.
It's fun to do a shot of malort with someone you just met. It's fun to give it to people who aren't from Chicago. It's fun to be in Chicago the first time and someone hands you one and says "welcome to Chicago buddy" and you drink it and think "What the fuck? These people are insane"
It's weird, it's not for everyone, it's a little much, it's unlike anything else, and yet it grows on you really quick. And I think that basically makes it Chicago in liquor form.
Do it. It's one of those things that's unpleasant but you get to bond with everyone else who's done it and it's over quick