Uptown

Uptown is one of Chicago's most historically rich and underrated neighborhoods — and arguably the best neighborhood in the city for music lovers. Home to the Green Mill Cocktail Lounge (open since 1907, a Prohibition-era speakeasy where Al Capone's associate 'Machine Gun' Jack McGurn was a part-owner and ran illegal moonshine operations), the Aragon Ballroom, and the Riviera Theatre, Uptown's Jazz Age entertainment legacy is woven into its architecture and its streets.

The neighborhood is a genuine value play. Yes, it's a bit farther north than River North or the Gold Coast — but it's going through real, positive change. New development is arriving, longtime institutions are thriving, and the lakefront is right there. Montrose Beach is the largest beach in the city. Montrose Point Bird Sanctuary — known as 'The Magic Hedge' — is one of the best birdwatching spots in the Midwest. The Black Ensemble Theater anchors a vibrant arts scene.

The Asia on Argyle dining district brings some of the city's best Vietnamese, Thai, and Chinese food to your doorstep. Two Red Line stops (Wilson and Argyle) connect you downtown in under 20 minutes. For renters who want a real neighborhood with history, culture, and lakefront access at a price that doesn't punish you — Uptown might be one of the best deals left in Chicago.