The Optima, Old Town's new dining and entertainment space, aims for a glamorous vintage atmosphere on two floors. Nibble steak and seafood, shareables like pierogies, pretzels and cheese and hummus in the 100-seat main dining room which has a fireplace for the cold months and garage-style doors that open to outdoor seating in summer. Climb up to the mezzanine level and notice semi private nooks and a state-of-the-art speaker wall spreading the sounds of musical artists and name DJs. The Marquee on floor two offers private banquettes with bottle service, a late night menu and the efforts of some of the city's hottest DJ's.
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. Resident DJ, Dante the Don, is well known (he's also the DJ for Cubs games at Wrigley Field), but you can also expect talent from around the world such as The Ying Yang Twins and Petey Pablo.
This dance club that also serves as a boozy salon is a great place for a manicure, martini, and dance party. The kitchy 60s decor includes glittery paint on the walls and salon furniture that would set your mom's heart (and hair) aflutter. Martinis & Manicures take place nightly until roughly about midnight and reservations are not required. Have a salon themed cocktail like the Bed Head, Deep Condition or Blowout and then dance the night away to live DJs or riotous theme parties. The 00's, hip hop or Prince nights combine the right amount of funk and nostalgia. There isn't reserved seating so all tables are available on a first come first served basis. Beauty Bar is a favorite of bachelorette parties, too. If you RSVP online, and arrive before 10 p.m. you don't have to pay a cover charge. Beauty Bar also has locations in cities like New York, Denver, San Fransisco and Las Vegas.
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 Psycho Bingo. Well, why not? The cultural Zeitgeist feels more than a little pathological these days, doesn't it? Bingo is followed by karaoke, every Wednesday night with grand prizes ranging from $200 cash, an iPad, Cubs and Lollapalooza tickets and smart TVs among the loot. Replay's Trivia Thursdays features beer specials and with more than 60 free vintage arcade games, including pinball, air hockey and billiards, it's a great 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?
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 who named the place after his mother who helped him open the club, still takes care of his guests every night.
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.
Don't let the name of the place fool you - while it has folky performers, this excellent, intimate concert hall offers shows ranging from African music to a full Cuban salsa band (with dancing!). The venue recently hosted Steve Earle, Lucinda Williams, Patti Smith and other cutting edge artists, too. There's not a bad seat in the theater, so don't hesitate to buy seats in the upper level. The venue, which is also a music school, was built by musicians for musicians. Ticket prices are extremely reasonable and even more so if you're a member. Parking is available across the street in a lot or along the street (both are metered). There are more than a few excellent restaurants on the block, so consider grabbing dinner before or after a show for a completely wonderful evening in Chicago.
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 wth 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 its 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.
No matter what night of the week you ache to get out, The Whistler has your back - and brain. There's a live show every night: 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 store front 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. Every second Friday is Singles Night when an all-vinyl dance party features soul, funk, boogie, and hip-hop singles spun at 45 RPM.
Visiting the Logan Square address at is actually a two-fer. Walk in downstairs and Slippery Slope promises a party night of dancing, DJs, a great beer selection, cocktails in bottles, Skee-Ball and raucous fun. Drinks are inexpensive, cash and credit card accepted. Did we mention that Slippery Slope is THE place for dancing in Logan Square? Upstairs, Heavy Feather offers a laid back but nonetheless happy 1970's vibe (not that anyone in the place was drawing breath in the 70's). You can have a conversation with a new friend you met dancing downstairs serenaded by Bowie, Fleetwood Mac and Stevie Wonder. Every Monday is a music happy hour that changes each week with different 70s artist.