Stepping foot in Uptown is like traveling back in time with its inspiring architecture and historical significance. This part of Chicago has always been a flurry of activity. With theatres, music venues, and a long stretching business district, it’s easy to see why.

The Red Line cuts through this busy neighborhood, spanning across four stations, but only 2 miles. Newly developed condos mesh nicely with the older two and three-flat buildings, and single family homes harken back to a distant time, and the rehabilitation of store fronts and venues give continuing life to Uptown.

The crown jewel of Uptown is its famed Green Mill. One of Capone’s speakeasies was found here, and tunnels would trail from there to the Aragon to easily smuggle booze during the Prohibition. While a little less gangster, colorful stories are still to be had in all of Uptown’s corners!

Whether you are channeling your inner 1920s ego or not, here are some Uptown offerings:


  • Demera
    This Ethiopian spot is great for first timers and die-hard fans of that tasty injera bread.
  • Hai Yen
    Pair your pho with hand rolled sausages, called bo la lot, at this Vietnamese place.
  • The Brass Heart
    A highly rated spot focusing on prix fixe with fresh seasonal ingredients.
  • The Reservoir
    More than a watering hole, this gastropub has hearty dining options for all.
  • Gigio’s Pizzeria
    A pie shop serving NY style pizza the size of a New York ego!


  • Wilson Yards
    Get all your skate gear at this outpost, then test it out at Montrose Skate Park.
  • Heritage Outpost
    Bikes and coffee go together well at this architecturally beautiful cafe.
  • Provisions
    Treats yourself or someone else to a fine bottle of spirits at this unique liquor shop.
  • SS Vintage Guitars
    In the market for a cool vintage guitar? This shop is for you!
  • Curious Creatures
    Maybe not for everyone, but you could find your pet bearded dragon here!


  • The Riviera
    A staple of the Chicago music scene for decades, this venue still rocks.
  • Aragon Ballroom
    Once a dancing club, this venue shows remnants of its former castle theme.
  • The Green Mill
    Al Capone, the best Jazz minds, tasty cocktails. The Mill is a legend.
  • Uptown Lounge
    This unassuming bar has karaoke and open mic- perfect for get togethers!
  • Carol’s Pub
    Honky Tonk has come to Chicago at this fun dive bar.

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