But that's not the point here. You buy this for the history, the look. The 'Chicago' stands out in any Jordan collection — it's the blueprint. Let’s talk performance — just kidding! This isn’t a performance shoe. The 'Air Jordan 1 Chicago' is all about style & culture. The leather creases, the sole is hard… you know this going in. Yet, every time I lace up this Air Jordan 1, I get why it’s iconic. It’s simple: you buy this for the look, not for groundbreaking comfort. Let's talk pros & cons, real quick. The biggest "pro"? Versatility and legacy. The Air Jordan 1 Chicago is a wearable piece of history. The downside? For its $180 price tag, the tech is "decades" old. If you prioritize modern comfort above all else? This might not be your daily driver. It's a style and culture pick first, a performance shoe... well, not so much. Who might want to pass? If you need all-day, walk-everywhere comfort – these ain't it. The break-in period can be real. Also, if you're not into high-tops or bold red shoes, maybe look at a different "air jordan 1" colorway. This is a statement piece. It's not the most "practical" sneaker, but for many of us, that doesn't matter at all.