In the midst of Chicago’s modernized North Side, one neighborhood stands above the rest in terms of preserving its illustrious past. Laden with rustic buildings, old theaters, and classic restaurants, Chicago’s Uptown neighborhood provides a unique backdrop for some of the city’s finest bars and pubs. By visiting these five bars with a little transportation help from Chicago Trolley, your Uptown Pub Crawl is sure to be an unforgettable night.
Green Mill Cocktail Lounge
4802 N Broadway St
Since this popular spot tends to get more crowded as the night goes on, we recommend going to Green Mill first to experience it without the crowds. Despite the fact this iconic establishment was a hotspot for Al Capone and other Chicago gangsters in the 1920s, this swanky lounge boasts some of the best live bar music in town. Listen some of Chicago’s most accomplished jazz and blues musicians as you sip down handcrafted cocktails filled with vintage flavor. Be sure to take in the atmosphere before making like a mobster and scramming to the getaway trolley.
5027 N Sheridan Rd
Heralded as one of the best LGBT bars in the city, Big Chicks provides party atmosphere you will want next on your Uptown Pub Crawl. This saloon-style bar run by Michelle Fire features one of the tastiest bar menus in the neighborhood. From incredible apps to sandwiches, burgers, fish, and potato skins, Big Chicks is the perfect place to fill up on all of your fatty favorites alongside cold pours. Plus, the bar tends to host solid dance parties on the weekends.
4840 N Broadway St
Next, follow the neon signs back to Broadway to experience the vintage aesthetic of Fat Cat. This bar’s classic exterior is juxtaposed with a surprisingly modern interior that features hit music, contemporary food options, and some of the best martinis around. With classy mixed drinks, an extensive craft beer menu, and friendly bartenders, Fat Cat will be the perfect halfway stop for your night in Uptown.
The Bar on Buena
910 W Buena Ave
Next, take the trolley south to the growing subdivision of Uptown known as “Buena Park” for the modern classic that is The Bar on Buena. With garage door windows, comfy couches, and plenty of beers on tap, this quality watering hole is sure to provide a more relaxed atmosphere where the beer selection is the focus. Thankfully, The Bar’s food menu is pretty impressive as well.
4000 N Sheridan Rd
Our journey ends in the Buena Park stronghold of Holiday Club. This flashy, 50s diner-style club offers an extensive cocktail menu, award-winning comfort food, and friendly staff. In addition to the classy atmosphere, Holiday Club hosts a variety of themed nights and events. Whether it’s a 90s party, themed trivia, or competitive karaoke, Holiday Club is sure to have something exciting happening that will be the perfect end to your Uptown Pub Crawl.
Did these suggestions get the ideas flowing? Book a trolley with us so we can drive you around Uptown while you and your friends focus on having a good time. We hope to hear from you soon!