Uptown

Perfect for

Living in Uptown

Uptown flies a little under the radar, but it has a lot going for it if you want more space, character, and a bit of calm without being too far from the action. It’s mostly made up of older walk-ups and vintage mid-rise buildings, so you’ll find more spacious layouts and generally more affordable pricing compared to neighborhoods further south. That said, updates can vary, some places have tons of charm, others feel like a time capsule. Uptown also has a rich history and a strong arts scene, with live music venues like the Aragon Ballroom and Riviera Theatre, plus access to the lake, Montrose Beach, and the Lakefront Trail. It’s quieter than Lakeview or Andersonville but still walkable, with solid food spots, local bars, and strong transit access. Downsides? Some blocks feel a little less polished, and not every building is super modern, but if you’re into space, culture, and lake access without the price tag, Uptown’s worth a look.