Uptown is home to a variety of bars that truly embody the charm of the neighborhood. Whether you’re into speakeasies that transport you back to the big band jazz clubs of the 1920’s, or neighborhood watering holes that make everyone feel welcome, there’s a spot for everyone in this north side community. Let’s take a look at six of these bars that are all a great place to start when visiting Uptown.
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The Green Mill Cocktail Lounge
Address – 4802 N Broadway, Chicago, IL

The Green Mill is a Chicago landmark, well known as a former Prohibition era haunt for Al Capone and his associates. Today, it’s one of the premier jazz clubs in the city, known for its vintage charm and outstanding live shows and music.
The bar has managed to maintain much of its original 1920s decor, including plush booths and art deco fixtures. While you’re there, you can really immerse yourself in the era by having one of their well-made Manhattans or a crisp martini. The Green Mill is cash only, however, so make sure to bring plenty of dollars if you plan on having more than one.
Fat Cat
Address – 4840 N Broadway, Chicago, IL
Just down the block from the Green Mill is Fat Cat, a more modern neighborhood bar that is a favorite among locals. contrasts with Uptown’s historic venues. At the Fat Cat you’ll find an impressive selection of craft beers and specialty cocktails, along with a menu of upscale pub food that includes gourmet burgers, poutine, chicken sandwiches, and more. The bar can get packed, especially on the weekends, but once you manage to get seated, you won’t regret spending an evening out at this great Uptown bar.
Uptown Lounge
Address – 1136 W Lawrence Ave, Chicago, IL

If you’re looking to have a drink before seeing a show at the Aragon Ballroom or Riviera Theater, then look no further than the Uptown Lounge. This bar, located next door to the Aragon, features a relaxed, unassuming environment with comfortable seating and a friendly vibe.
Uptown Lounge serves a wide range of beers and inventive cocktails, while their kitchen serves hearty American pub fare, ideal for a pre-show meal or late-night snack. They also host karaoke nights throughout the week, just in case you want to put on your own concert instead.
The Bar on Buena
Address – 910 W Buena Ave, Chicago, IL
In the Buena Park area of Uptown sits The Bar on Buena, a cozy neighborhood spot that offers a refined selection of craft beers and spirits. This bar is perfect for summertime get-togethers, as it offers ample patio seating in a somewhat quieter area of the Uptown. The food menu features a mix of local and international pub fare, with everything from a Chicago style popcorn mix to tacos available to snack on.
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Carol’s Pub
Address – 4659 N Clark St, Chicago, IL
Carol’s Pub has been a staple in Uptown since 1972, and is known for its country music, live bands, and late-night honky-tonk vibe. It’s a place where you can kick back with a cold beer while enjoying some live country music.
The lively dance floor at Carol’s combined with the relatively cheap beers will ensure that the energy is kept high until the early morning hours. There is also a snackbar with everything from burgers to chicken tenders on the menu. The atmosphere at this bar is informal and unpretentious, so feel free to let your guard down and come ready to dance and to have a good time.
Larry’s at the Lawrence House
Address – 1020 W Lawrence Ave, Chicago, IL
Located in the lobby of the historic Lawrence House building, Larry’s is a cocktail bar that blends modern sophistication with vintage elegance. This spot is perfect for those who are looking to conversate while enjoying hand crafted cocktails.
The bar features original 1920s architecture, including terrazzo floors and ornate ceilings. The menu is frequently updated to reflect seasonal ingredients and innovative mixes, and while cocktails are king here, there is also a small selection of craft beers and wines available too.
Each of these bars, and the many others in Uptown, prove why Uptown should not be overlooked when planning a night out in the city. These establishments are not only places to enjoy a drink but also spaces where music, history, and local culture continue to thrive. Whether you’re an Uptown resident or are just passing through, make sure to stop by one of these venues for a perfect start to your night.


