We all know Chicago makes its way on every ‘best Midwest’ listicle, but we had to push our eyeballs back in place when we saw what followed the “Windy City” on Midwest Living’s 2026 awards. The truth is the Midwest is more diverse than you might think — a far cry from desolate corn fields …

There’s no Midwest city more famous than Chicago. Next up, it’s up to your discretion. St. Louis, Cleveland, and even ever-so-trendy Indianapolis are all in the mix. If we’re being honest, not every Midwest city, no matter how well-known or hyped, is worth visiting. I mean, when’s the last time you heard about someone vacationing …