Watch CBS News

Best Hipster Hangout Spots In Chicago

By Marcherie Davis

Looking for great food and drinks to enjoy alongside the company of like-minded, free-thinkers such as yourself? Then look no further than this list of awesome haunts to enjoy just that. These Chicago venues offer live entertainment, cool theme nights, bar games, cheap drinks and good eats. While each of these Chicago hotspots boast a unique quality that makes them great places to party, they all have one thing in common: they're perfect spots for the city's hipster crowds to gather, converse and sip on some cold beer.

Nightlife & Music Hipsters, Skylark
Photo Credit: Skylark via Facebook

2149 S. Halsted St.
Chicago, IL 60608
(312) 948-5275

Stop by the Skylark every Monday night around 10 p.m. to catch some live music—just bring $5 for the suggested donation, all of which goes straight to the musicians performing that night. The beer list here, while varied, is also quite affordable, and you'll be hard pressed to find brews with less than 5% ABV (hint: the highest is the Founders Double Trouble, an IPA with 9.4% ABV). The kitchen is open until at least midnight, and vegetarians can snack on grilled cheese while enjoying sounds from the jukebox in the laid back, somewhat divey (but always casual and friendly) atmosphere. While this is a great spot for music lovers, sports fans should steer clear, as the Skylark won't be showcasing games on its non-existent TVs anytime soon.

Nightlife & Music Hipsters, Wise Fools Pub
Photo Credit: Wise Fools Pub via Facebook

Wise Fool's Pub
2270 North Lincoln Ave.
Chicago, IL 60614
(773) 929-1300

Wise Fools Pub is a Lincoln Park staple that has it all: great daily drink specials, live entertainment and bar games. This pub has something for everyone. Music lovers can catch performances from both travelling and local bands, beer drinkers can choose from more than 80 different kinds of draft and bottled beers and penny pinchers can revel in the savings that accompany 50 cent Miller High Lifes, free popcorn and a new drink special every day. Sports fanatics can partake in some pool or darts in between watching the game on one of the six TVs or the bar's projection screen, and dog owners can bring their best friends, as Wise Fool's is a pooch-friendly pub.

Nightlife & Muisc Hipster, Whistler
Photo Credit:

The Whistler
2421 N. Milwaukee Ave.
Chicago, IL 60647
(773) 227-3530

This three-in-one hotspot in Logan Square is part bar, part art gallery and part live music venue. Go for the art, which showcases a new installation from a local artist every other month, and stay for the award-winning cocktails and great entertainment. Sip on a Daley Sour (apple brandy, cinnamon syrom, lemon, egg white and Malort) while taking in the sounds of local musicians, DJs and bands--all free of cover--on any given night of the week. The Whistler's calendar is always up-to-date, so you can sync your visit up with your music of choice. And if you're a hipster who also happens to be a musician, you can email the bar about booking a performance for a view from the other side of the stage.

Nightlife & Music Hipsters, McFadden's
Photo Credit: McFadden's via Facebook

1206 North State Parkway
Chicago, IL 60610
(312) 475-9450

McFadden's is a great place for hipsters to hangout until the wee hours of the morning, any day of the week. The bar has various daily drink specials and theme nights. Brainy hipsters who also like to take advantage of some great food and drink specials should stop into McFadden's on Tuesdays for some "Trivia with Tim" at 8 p.m. There's a chance to win a $200 prize and specials such as $1 tacos, $2 Coronas, and $3 Cuervo shots. This place also has nine 42" televisions and boasts great music, which is regularly provided by some of Chicago's hottest DJs.

RelatedChicago Sports Bars To Root For The Other Team

Nightlife & Music Hipsters, Halligan
Photo Credit: Halligan via Facebook

2274 North Lincoln Avenue
Chicago, IL 60614
(773) 472-7940

Open till 2 a.m. every night, (or morning, if you want to get technical about it) Halligan's is a great haunt for local hipsters in the Lincoln Park area. During the prohibition, Bugs Morans and John Dillinger were regulars at the tavern that occupied this space during the time. Now, hipsters saunter through for the monthly featured drink and shot, as well as to take advantage of the bar's great daily drink specials. This roomy spot is a great place to kick back and enjoy a cold beer. Every third Wednesday of the month, Halligan's participates with other area bars for the Lincoln Park Derailed monthly pub crawl, which includes $3 312 and Budweiser, $4 Fireballs, and $5 Absolute cocktails.

Related: Chicago's Best Old Timey Bars

Big Star
1531 N Damen Ave.
Chicago, IL 60622
(773) 235-4039

If you're a hipster who not only loves tacos, but also thinks they go down best with a shot of reasonably priced tequila or whiskey, Big Star is your bar. Located in the Wicker Park neighborhood, this spot is always packed, both inside and out on the patio. Beer drinkers should check out the 3 Floyds brews on tap, and taco connoisseurs rave about the pork belly fish versions Big Star cooks up. If you're looking for a night of light-hearted conversation with a few friends, this is bar is not ideal, but if you don't mind waiting in line for some loud music and a boisterous crowd, Big Star delivers on all counts.

Marcherie Davis is a freelance writer who enjoys arts, culture, and most genres of music. In addition to CBS Local, she writes for and Gapers Block. She is also a single parent who enjoys occasionally dabbling in crafts such as crochet and knitting. Her work can be found at

View CBS News In
CBS News App Open
Chrome Safari Continue
Be the first to know
Get browser notifications for breaking news, live events, and exclusive reporting.