Fat Cat bar represents the best of classic American fare. You can’t go wrong with Trivia Tuesdays or Mussel Pot Wednesdays. With awesome burgers like the Hot Mess (an amazing reimagining of the Big Mac) and TVs that always have the game on, the Fat Cat is an ideal location to watch football on those slow Sunday mornings.
Fat Cat, 4840 N Broadway St, Chicago, IL, USA +1 773 506 3100
The Green Mill
The Green Mill draws a lot of its fame from its historic past; it was frequented by the infamous Al Capone. For this reason, and because it is featured in nearly every Chicago tourist pamphlet, the Green Mill can perhaps be classified as ‘touristy.’ However, you absolutely cannot let that stop you from checking it out, as The Green Mill is possibly the crown jewel of Uptown. It hosts some of the best shows in the city, featuring the most talented comedians, poets, and musicians that Chicago has to offer.
The Green Mill, 4802 N Broadway St, Chicago, IL, USA +1 773 878 5552
One of the many LGBT-friendly bars in Uptown, Big Chicks celebrates local artists, as well. The sister restaurant to Tweet, the delicious brunch restaurant next door, Big Chicks features wall-to-wall art created by local talent. Big Chicks is famous for its friendly atmosphere, Dollar Burger Night, and free shots at midnight.
Big Chicks, 5024 N Sheridan Rd, Chicago, IL, USA +1 773 728 5511
Crew Bar and Grill
You’ll be hard-pressed to beat the Crew Bar and Grill come football Sundays. At Crew Bar and Grill (Chicago’s Premier Gay Sports Bar), you can enjoy the game in peace, as well as mouthwatering bar food and great cocktails.
Crew Bar And Grill, 5024 N Sheridan Rd, Chicago, IL, USA +1 773 784 2739
The SoFo Tap
LGBT friendly SoFo Tap has an extensive collection of drinks and a great backyard beer garden. In a way, The SoFo Tap is two bars in one; sometimes it’s a relaxed place to go and throw a few darts while you nurse a drink, and other times it’s a popular local spot for karaoke or a goofy live game show night.
The SoFo Tap, 4923 N Clark St, Chicago, IL, USA +1 773 784 7636
Marty’s Martini Bar
If you’re looking for a drink that is not only a work of art but also potent as hell, look no further than Marty’s Martini Bar. Constructed in the style of a Prohibition-era speakeasy, Marty’s Martini Bar serves colorful cocktails, including The Dirty Bird (vodka and olive juice with blue cheese-stuffed olives). Marty’s small but inviting atmosphere, professional staff, and ‘different strokes for different folks’ attitude make it a great neighborhood watering hole.
Marty’s Martini Bar, 1511 West Balmoral Ave, Chicago, IL, USA +1 773 454 0161
Simon’s Tavern is rivaled only by The Green Mill in Uptown as the historical mainstay of the Uptown/Andersonville area. After it was converted from a speakeasy for the neighborhood’s Swedish population, Simon’s Tavern became a fixture of the neighborhood. Longevity comes with a price, it would seem, as the Tavern is rumored to be haunted by the spirit of a woman caught up in a torrid and violent chain of events. Mysterious history aside, Simon’s Tavern serves people from all walks of life; looking down the bar, you’d be hard pressed to pin down a majority demographic.
Simon’s Tavern, 5210 N Clark St, Chicago, IL, USA +1 773 878 0894
The Decibel Bar in Uptown is a low-key local bar and locals hangout. Marketed as an Asian Fusion Bar, it is one of the best places at which to enjoy good food and even better local jazz, blues, and rock and roll. The kitchen is open late and strengthened by the quality, professionalism, and friendliness of the service staff.
Decibel Uptown, 4437 N Broadway St, Chicago, IL, USA +1 773 944 5900
The Bar on Buena
The Bar on Buena is a local comfort spot; multiple TVs, a rotating list of craft beers, and quality Tex-Mex bar food that’ll settle you in for the long haul. The Bar on Buena is a dream realized by two high school friends who wanted to own their own sociable neighborhood bar. They definitely succeeded. The atmosphere is high-energy, but it doesn’t impede upon your personal conversations.
The Bar on Buena, 910 W Buena Ave, Chicago, IL, USA +1 773 525 8665
While there is a seemingly impossible collection of delectable Asian restaurants in Uptown, Agami leads them all in both atmosphere and quality of food. The dim lighting and professional wait staff make Agami the premier location for date night. Like most sushi bars, Agami offers classic and more traditional rolls, but if you’re not a purist, then the Chicago Bulls Roll (spicy blue crab and baked scallops topped with grilled tiger shrimp in spicy garlic sauce, guacamole, and pico de gallo with golden aioli and unagi sauce) will blow your taste buds out of your mouth.
Agami, 4712 N Broadway St, Chicago, IL, USA +1 773 506 1845