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Chicago's entertainment varies from loud and loose to sophisticated and sedate. You'll find classic Chicago corner bars in most neighborhoods, along with trendier alternatives like wine bars and lounges. The strains of blues and jazz provide much of the backbeat to the city's groove, and an alternative country scene is flourishing. As far as dancing is concerned, take your pick from cavernous clubs to smaller spots with DJs spinning dance tunes; there's everything from hip-hop to swing. Wicker Park/Bucktown and River North have the hottest nightlife, but prime spots are spread throughout the city.
Shows usually begin at 9 pm; cover charges generally range from $3 to $20, depending on the day of the week (Friday and Saturday nights are the most expensive). The list of blues and jazz clubs includes several South Side locations: be cautious about transportation here late at night, because some of these neighborhoods can be unsafe. Drive your own car or ask the bartender to call you a cab.
Pops got its start more than 40 years ago and it's Chicago's only champagne bar. These days there's a focus on small-grower producers. The basement is home to Watershed, a cozy spot with limestone walls focused on Great Lakes regional craft beers and spirits.
A neighborhood lounge that turns DJ-driven dance spot late at night, this newer entry on the Halsted Street strip makes a striking statement with its signature visual, a cloud-like illuminated ceiling sculpture that's visible from the street.
Chicago hipsters and indie rockers have made Rainbo Club their unofficial meeting place. Apart from the working photo booth wedged into a corner, the stripped-down hangout is pretty barren, but drinks are dirt cheap and the crowd is loyal.
Devoted to the Chicago-bred tradition of improv comedy, the Revival features top local talents. The theater relocated from Hyde Park to the South Loop in 2024.
Chicago has evolved one of the country’s best craft-brewing scenes, but back when the pickings were slim, Revolution was here, satisfying drinkers thirsty for something more interesting than watery macro brews. The Milwaukee Avenue location is a good place to work your way through a flight of the house beers---the offerings skew toward classic German styles and hop-forward IPAs---while lining your stomach with unfussy pub grub like burgers and fried cheese curds. (There’s also a taproom in nearby Avondale with a less-polished vibe and a limited menu of nibble-y things.)
It’s hard to imagine a bar feeling homier than Rogers Park Social. The community-oriented spot has an impressive menu of craft beers plus fresh cocktails that pack deep layers of flavor into every glass.
One of the city's hottest perches, ROOF occupies the 27th floor of theWit Hotel. The outdoor space entices with firepits and panoramic city views; floor-to-ceiling glass windows make the indoor area equally breathtaking. DJs spinning eclectic beats and a menu of pricey cocktails and small plates complete the scene.
A longtime favorite, Roscoe's Tavern has a lot to offer its patrons, including a full all-day dining menu, jam-packed front bar, a dance floor, a pool table, an outdoor garden, DJs on the weekends, and a sidewalk café in warmer weather. When it's airing, Roscoe's also hosts Drag Race aftershows that regularly feature former contestants.
Grab a biscuit and a tang (that is, a shuffleboard disc and cue) and embark on a vacation within a vacation at this Brooklyn import, featuring 11 shuffleboard courts (one of them up on a seasonal rooftop deck) that channel a retro cruise ship, as well as a rotating lineup of food trucks and tropical cocktails. Courts are first come, first served; to minimize the wait, try turning up at opening time (that's 5 pm on weekdays, and noon on weekends).
Built as a "tied house" in 1903 by the Schlitz Brewing Company (whose logo still adorns the exterior), Schubas Tavern favors local and national power pop, indie rock, and folk musicians. The laid-back, wood-paneled back room is the perfect place to hear artists who are just about to make it big. The attached and appropriately named restaurant, Tied House, serves creative comfort food.
That the once-shabby stretch on which the Scofflaw sits grows hipper by the month is no coincidence; the cozy, brick-walled cocktail bar, which boasts a huge collection of gin, put the intersection of Kedzie and Armitage Avenues on the map. The kitchen—which turns out one of the city's best burgers—stays open till 1 am.
With a shaded beer garden in summer and a roaring fireplace in winter, Sheffield's spans the seasons. The laid-back neighborhood pub with a craft beer and barbecue focus features more than 100 kinds of bottled beer, including an impressive list of vintage brews. You can also choose from up to 50 beers at one of the four bars, but for those not interested in brews, wine and cocktails are also available.
In business for over 40 years, this sprawling, multi-level club packs them in by the hundreds each weekend thanks to the fairly priced drinks (and extremely rare cover charges). Events include show tune singalongs, glow stick dance parties, lesbian-friendly Sapphic Saturdays, and even events for dog owners.
You can catch small indie bands, DJs, and local acts at this concert space that also doubles as a coffee shop in the morning and a beer garden (with dozens of options on draft) in the afternoon and evening.
With its giant dance floor, craft cocktails, and dim, red-hue lighting, Slippery Slope has brought a cool, clubby vibe to Logan Square. (It gets bonus points for the Skee-Ball machines located next to the door.) This place gets especially crowded on the weekends, when the dancing gets serious.
Of all the sports bars in Wrigleyville, Sluggers is perhaps the most famous. It's always packed before and after Cubs home games (and the ballplayers make occasional appearances in summer). Sluggers has a little bit of everything, including 40 TVs, fast- and slow-pitch batting cages, Skee-Ball, pool tables, air-hockey tables, electronic basketball, arcade games, and even a dueling-pianos show on the weekends.
Sound-Bar is a two-level labyrinth of nine bars, each with a unique design and color scheme (some even serve matching colored cocktails). Feel like dancing? Join the pulse of Chicago's best-dressed on the huge dance floor.
This Ukrainian Village bar’s roots as a nightspot for local Polish immigrants can still be felt in its warm wood accents and retro backbar. Classic cocktails are the drink of choice; they pair perfectly with the warmth of the back patio’s brick fireplace.
This late-night underground dance club has been in the River North area for more than 25 years. Featured are internationally renowned and up-and-coming local musicians and DJs.
Check the letter board over the front door of this Wicker Park storefront for a list of the rising indie rock and hip-hop acts playing there soon, often on their first Chicago gigs. Chances are good they'll be playing a larger venue the next time through. Locals also come for the popular Thursday reggae nights and regular open-mic events.
Once you’ve found the alley entrance (hint: look for the red-roped line of people waiting outside), descend the glowing skull-lined stairs to reach this hip spot that’s an homage to the mid-century tiki craze. "Three Dots and a Dash" is an old-school, rum-based tiki cocktail that gets its name from the morse code for the letter "V" as in victory, as used in WWII. There are Pan-Pacific nibbles, like the shareable pu pu platter, to accompany the strong tropical cocktails adorned with flowers and served in tiki mugs.
At the far north end of the Southport Corridor sits this humble neighborhood watering hole with a wide range of offerings that somehow all work well together. It's a Kansas City-supporting sports bar, with a menu offering New Orleans-style po'boy sandwiches, while also serving some of the city's best deep-fried buffalo wings. Toons also has an impressive beer list for a casual sports-focused environment, with 20 taps serving drafts from the likes of Dovetail, Three Floyds, and Haymarket. Need a budget beverage? Order a Chicago Handshake: a pint of Old Style paired with a shot of Malört.
This subterranean dance club has dropped the quasi-military underground bunker theme it once sported, but it still attracts celebs, international DJs, and the clientele that follows both.
The Violet Hour channels a Prohibition-era speakeasy—an unmarked door in the mural-covered facade leads to a mysterious, curtained hallway. Inside, twinkling crystal chandeliers cast a glow on cornflower-blue walls, and extremely high-backed blue leather chairs encourage intimate conversations. Add to that pricey but flawlessly executed cocktails and a small menu of refined snacks, and it's our idea of nightlife heaven.
This long-running cozy, candlelit bar is a romantic place for a date. It stocks more than 500 bottles of wine (at least 20 are available by the glass) plus ports, sherries, single-malt Scotches, a few microbrews, and a menu of small tasting entrées at reasonable prices. At $20 for 3 pours, the Monday evening self-guided blind tastings are a hit with neighborhood oenophiles.
This is the place for infectious live reggae, world-beat music, and Caribbean cuisine Tuesday through Sunday. Take a breather at the bar and sip a signature Famous Wild Hare Rum Punch or a Jamaican Red Stripe beer.
At this favored no-frills tavern, locals and university students gather for beer, burgers, and Reuben sandwiches. Every second Sunday night, there's a free-form blues jam session followed by live jazz.
Zanies books outstanding national talent and is Chicago's best stand-up comedy spot. Dave Chappelle, Ali Wong, and Jeff Garlin have all performed at this intimate venue.
Small and funky with zebra-striped lamps and other kitschy accoutrements, this lounge attracts an interesting crowd of dressed-up and dressed-down regulars who come to sing along with the pianist on duty.
