Best Nightlife in Chicago

Dance, music and comedy clubs among the best in Chicago nightlife

Nightlife is no longer just an ear-splitting dance club or bars bursting with weekend revelers - although there are plenty of those from which to choose in Chicago. Evening diversion is as diverse as the city itself, with destinations specializing in comedy, arcade games, burlesque, live jazz, blues, hip-hop and rock 'n' roll sets. There's something for the flannel shirt and jeans set as well as those who feel compelled to out-sparkle everyone else. 

Explore Chicago nightlife downtown at The Underground Chicago, one of the city’s hottest dance clubs, or the brand new Flash Dance Club inspired by Andy Warhol’s Factory. The historic yet thoroughly current The Second City Theater Chicago lampoons the news that already absurd and the "cast delivers a show that’s surreal, musical, maniacal, and utterly entertaining all at the same time." Don't forget about the on-site UP Comedy Club hosting nationally known comics and improv comedy shows. For sheer fun, Replay Lincoln Park is a popular vintage arcade bar offering weekly themed trivia and ever changing pop-up pop culture themed immersive shows. Logan Square's The Whistler is a craft cocktail lounge, art gallery, in-house record label and live music venue that hosts a mix of local live music, DJs, a weekly jazz series, LGBTQ dance parties, 80s Japanese Disco and new wave DJ sets.

For a lively lounge experience, head to the landmark Green Mill Cocktail Lounge for jazz or Rosa’s Lounge for blues. An unpretentious Pilsen bar transforms into an equally unpretentious music and dance venue by night with entertainment as diverse as the guests - that would be the Giant Penny Whistle. For a night in the stars with a jazz soundtrack, get to the 13th floor of Hotel Lincoln and the J. Parker. 


For the other half of the world that doesn't care for stilettos, musky cologne, packed dance floors and endless selfies, there's Replay Lincoln Park, a popular vintage arcade bar offering weekly themed trivia and ever changing pop up pop culture themed immersive shows. There has been Moe's Tavern, Game of Thrones, Fyre Fest, The Salty Spitoon, Schitt Happens, Marvel Arcade, 90s Nickelodeon and the Squid Game is currently running. Check out Replay's Trivia nights (like Harry Potter trivia) while enjoying a nice selection of craft beer and cocktails. Sample more than 60 free vintage arcade games, including pinball, air hockey and billiards. It's a comfortable fun hang any night of the week. Shooters, signature cocktails and an extensive craft beer menu means no one goes thirsty. Who says "nightlife" needs an EDM beat?

Recommended for Best Nightlife because: Replay Lincoln Park's extensive craft beer menu and collection of free-to-play vintage arcade games and pinball machines work for the anti-dance club crowd.

Jacky's expert tip: Friday Happy Hour features half-price drafts from 4 - 8 p.m. Plan a visit Thursday through Saturday to enjoy DJs.

Read more about Replay Lincoln Park →

Rosa's Lounge, circa 1984, is not a 21st-century re-creation homage to family-owned blues bars - it's the real deal. When you want to hear great live blues without pretension but plenty of sincerity - this is your destination. Order a drink and enjoy the diverse crowd that fills Rosa's to hear the likes of harmonica genius Sugar Blue, Lil' Ed & The Blues Imperials and Billy Branch & the SOB. There is a cover charge and full-service bar to meet guests' needs (no drink minimum). Tony, the friendly owner, named the place after his mother who helped him open the club, and he still takes care of his guests every night. It's a sweet place.

Recommended for Best Nightlife because: Rosa's Lounge is a friendly, family-owned blues club where you can see the country's top blues names in an intimate setting.

Jacky's expert tip: Fill your belly before because Rosa's serves only sturdy drinks, smiling faces and great music. Good bets include Giant ($$$) or any of the inexpensive taquerias.

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Lincoln Park

Chicago adores its rooftops but as soon as the cold winds begin to blow, the hotspots cool off and shutter. Not so the J. Parker atop Hotel Lincoln. The year-round, retractable rooftop setting on the 13th floor serves up a craft cocktail menu that changes seasonally as well as craft brews, ciders, wine and spirits. Scan the heavens and order a Message from Mars, a tropical Saturn's Return or a ginny Pluto Matters. Snuggle by the glass fire pits and take in 180-degree unobstructed views of Lincoln Park, Lake Michigan and the urban skyline. There's live jazz on Wednesday evenings (6-9 pm) and check the web site for DJ entertainment and themed special events. Open until 1 a.m. on weekends, the J. Parker offers nosh for the night like short rib egg rolls, Nashville hot chicken, soy ginger wings, J Parker burger, smoked pork belly, Buffalo cauliflower and churro fries.

Recommended for Best Nightlife because: The J. Parker offers what most other Chicago rooftops don't - year-round views up the sky plus impressive cocktails, bites, live jazz and special events.

Jacky's expert tip: Breakfast is served in the skies Monday through Friday from 7-11 a.m.

Read more about The J. Parker →


The Underground nightclub takes its tenor of exclusivity seriously with a military theme and unmarked basement level entrance. Those who live for a see-and-be-seen atmosphere feel right at home here. Bottle service and celebrity sightings are de rigueur after accessing the cavernous bomb shelter entryway where DJs spin until the sun comes up and candlelit ammunition crates serve as tables to hold your top-shelf cocktails. Party with a mix of Chicago-based DJs and nationally-recognized musical performers. You can also expect top electronic and dance music talent from around the world such as Olivier Giacomotto, Robbie Rivera, dance/pop duo Vavo and DJ Lucati.

Recommended for Best Nightlife because: The Underground hosts nationally-recognized artists year-round and during Lollapalooza afterparties including the likes of Ludacris, Wale, The Cool Kids and others.

Jacky's expert tip: Packed to the rafters by midnight, the club churns with partiers on theme nights that range from costume parties to fashion shows.

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Chic and sexy, Untitled Supper Club is an upscale dining and entertainment spot with a prohibition-era atmosphere. In addition to an American supper club menu, the venue boasts the country's largest collection of curated American Whiskeys (more than 550 plus seven Michelin Bib Gourmand awards) which should get you in the mood for live entertainment. With differently designed rooms and four bars - the Library, Cabaret, Back Stage and Drawing Room - you're sure to find something appealing. Untitled offers tribute shows, sensual burlesque performances and Absinthe Minded featuring ambient performances, specialty cocktails, and one of the only opportunities for Chicagoans to experience tableside Absinthe fountains.

Recommended for Best Nightlife because: Burlesque and variety shows, tribute performances, supper club menu and the country's largest collection of curated American Whiskeys add up to some fine nightlife.

Jacky's expert tip: Untitled is open Wednesday-Saturday and the atmosphere can change by the evening or even by the room within the space.

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Inspired by Clark Monroe's Uptown House in 1940's Harlem, the Green Mill attracts tourists and jazz aficionados nightly. Once a hangout of Al Capone, Charlie Chaplin and Gloria Swanson, the Green Mill has what modern clubs lack - character. It was also a speakeasy during Prohibition and retains an early 20th-century look and feel. The live music schedule is packed with jazz, big band, blues, and swing music, plus the popular, long-running Uptown Poetry Slam on Sundays. Cocktails are inexpensive, but if you want to enjoy them from a table, get there early and definitely before the bands go on. Expect jam sessions with local artists as well as name musicians performing traditional, contemporary, Bebop and improvisational jazz.

Recommended for Best Nightlife because: Green Mill is perfect for those who appreciate live jazz in an informal but classy atmosphere.

Jacky's expert tip: If you want a table, get to the cash-only venue early and enjoy cocktails before bands play their first note.

Read more about Green Mill Cocktail Lounge →

No matter what night of the week you ache to get out, The Whistler has your back - and brain. There's a live show most nights: it could be jazz, rock, electronic, country, soul, Movieoke (karaoke to movie clips), film screenings, DJ sets, readings and other various and sundry entertainment to tickle your neurons and move your body. It's also a craft cocktail bar and offers a storefront art gallery so you can sip, observe and remark about the state of art, music. politics, the Infinite You (that's a cocktail) and then have another. Currently The Whistler is open at reduced capacity Wednesday and Thursday from 6 p.m. - 1a.m., and Friday and Saturday from 6p.m. - 2a.m. Guests are required to be fully vaccinated (last shot two weeks prior to entrance date) with proof at door. Check the web site for frequent one-off events that feature soul, funk, rock and hip-hop tunes.

Recommended for Best Nightlife because: Travel guides adore The Whistler for reasonably priced, creative drinks and locals love it for its commitment to local musicians and artists.

Jacky's expert tip: It can be a squeeze on weekends so remember there's outdoor seating in the summer in the patio out back.

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Forrest Gump could have said, "Life is like a night at the Giant Penny Whistle, you never know what you're going get." It could be honky tonk and country classics or disco, House, R & B, Salsa, Cumbia or Hip-Hop. Just beyond an unassuming facade, the venue reveals an expansive tavern and music spot that transforms from a neighborhood watering hole for a shot and a Hamm's to a late night dance and music club with cocktails like the "Freakin' Puerto Rican" and the "Sonic Doom." With music this eclectic, expect diverse clientele and a different vibe every night. Visit on Tuesday and Thursday for Silk and Tribe dance parties. The tavern is dog friendly before 10pm and when all that dancing and socializing gets you hungry, Coyotes on 18th street is a good bet for late night grub. Feel free to bring in bar snacks from La Michoacána across the street.

Recommended for Best Nightlife because: Unpretentious bar transforms into an equally unpretentious music and dance venue by night with entertainment as diverse as the guests.

Jacky's expert tip: Parking up front is free after 10pm and or scour side streets for free parking.

Read more about The Giant Penny Whistle →

Lincoln Park

If you "love the nightlife and got to boogie on the disco 'round, oh yeah," get thee to the new Flash Dance Club. Inspired by Andy Warhol's Factory, the venue whisks revelers back to the disco era with pop art, flashing lights and multiple bars decorated in shattered mirrors (a la Warhol's Factory). Slip onto the big red couch In the Banana Lounge and relax before enjoying Chicago artists in the Lounge and two-story Flashback Room late into the night - the club stays open until 4am on Friday and 5am on Saturday. Order bottle service from a six-pack of Red Bull to a magnum of Grey Goose or Dom Perignon. The venue is open Friday and Saturday nights. Book a table in the front room, the dance floor or The Pad (back room second floor).

Recommended for Best Nightlife because: You'll wonder if Bianca Jagger and Cher are just around the corner at the club whisking revelers back to the wild, care-free disco era.

Jacky's expert tip: Arriving by midnight is ideal. There's adequate street parking along Lincoln Ave.

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Who doesn't need a few laughs during the cultural chaos that is life in the USA? The world's premier comedy theatre and school of improvisation, Second City, pokes fun at boomers, millennials, media, and the *&%#@! going on in DC. Everyone with a pulse knows that Second City launched some of the biggest names in the business, including Steve Carell, Stephen Colbert, Tina Fey and countless others. Since its creation in 1959, the show claimed Old Town it's home when the founders wanted a theater to practice their own, Chicago-style routine of sketch and improv. The small audience is packed in front of a sparse stage with only a few chairs, and the show covers current topics, followed by some improv using audience-suggested topics. If the main stage is sold out, don't hesitate to see Second City, etc.or some stand up at adjacent Up Comedy Club.

Recommended for Best Nightlife because: The Second City has launched some of the biggest names in the business including Tina Fey and Stephen Colbert.

Jacky's expert tip: Make a plan to eat at a nearby restaurant before hitting the 11 pm show. Twin Anchors (1932) and Fireplace Inn (1969) both ooze nostalgia.

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Meet Jacky Runice

Born in Bucktown when bulletproof was a home safety choice and not a coffee order, Jacky Runice has been knocking around Chicago as a professional print, online and broadcast journalist and...  More About Jacky