A good jukebox can make your night, or at least give you something to do when the conversation lulls; a bad one can turn a good bar into a nightmare in the span of one ill-timed Bon Jovi selection. We're not talking about those Internet-enabled touch-screens that offer any song under the sun; no, we mean real, honest-to-goodness jukeboxes with creaky page-turners and frayed, sometimes handwritten album covers. Read on to find out which spots will help you keep your head nodding all night long, with a minimum of clunkers to kill your buzz.
AliveOne
If the word "bootleg" makes you think of more than just Prohibition Era smugglers, this live music haven is for you. The jukebox is packed with live performances from esteemed rock acts of yesterday and today…no polished studio sets here. Grab a beer and transport yourself to that awesome Wilco concert last summer, or that acid-fueled Grateful Dead romp you've always imagined but never experienced. But please, no shouts of "Freebird."
10pin Bowling Lounge
River North's upscale bowling alley and eatery features something a little different: a video jukebox. Pop in a buck and you're a burgeoning Bill Bellamy, projecting old Del the Funky Homosapien videos on the giant flat screens in front of the bowling hordes. The selection is a strange mix of old (Roy Orbison's "Only the Lonely" in glorious black and white), new (Electric Six's hilarious "Gay Bar"), cool (Siouxsie and the Banshees) and downright egregious (Snow's repugnant "Informer"). Whatever you pick though, it's a lot of fun, and you get the feeling some of the tracks will get more play here than they ever did on MTV (big surprise there). Serious bowlers will do well to take note of the dancing that accompanies the televised beats...watch, learn and bust a new move to celebrate any and all strikes.
Green Mill
It makes sense for one of the nation's oldest and best jazz spots to have one of Chicago's most impressive jukeboxes. Classic 45s include a long list of jazz and big band standards, many from performers who have graced the Green Mill stage at some point in its staggering near-100-year history. Singles from the likes of Billie Holiday, Lena Horne and Marlene Dietrich mingle with Big Band standards from golden-agers Glenn Miller and Gene Krupa. The collection looks like it's been cryogenically frozen at around 1952, and the sound is every bit as deep, woody and romantic as the ultra-smooth environs in which it resides. A genuine treasure, at prices that seem 1952-like as well.
Schubas
Schubas is already known for its role in the upper echelon of up-and-coming indie and alt-country acts presenters, and for good reason. Its performance space seems born to stage an elementary school Christmas pageant, which translates into some pretty serious intimacy. It goes with the territory then that Schubas employees keep the front bar's juke stocked with a stellar collection of local and national acts. Even when shows are on (which almost always seems to be the case), you can still catch the top-notch collection with a drink in hand (and a quick round in the photo booth to boot). Want to hear some tracks off of Arcade Fire's "Funeral?" Check. Love the Decemberists' album "Picaresque?" Got it. Eager to hear something from local folk rocker Robbie Fulks? You're set on all fronts.
Small Bar (Wicker Park)
Need a fix of the Pixies? Smallbar's got it…plus Fugazi, Weezer and any other nostalgia-inducing band from the early '90s, not to mention a nice selection of classic rock and vintage country. The crowd here knows its music almost as well as it pretends to know the 125 beers on the menu, so you'll rarely be shaking your head in disgust at a pick. But with so many eager DJs, you may have to wait a while before your dollar does any good.
Marie's Riptide Lounge
The people at Marie's know how to make the best of nearly any song; some nights, you'll find the entire bar singing along to Frank Sinatra or Petula Clark. The throwback choices (including Elvis, Tom Jones and Wayne Newton) are harbingers of the Riptide Lounge's classic charm, something you might otherwise forget given the young, hip crowd that begins to pack the place after 1 a.m.
Artis's Lounge
Artis's might have the best jukebox you'll never hear. Not just because it's a little out of the way on the South Side, but because most nights, a real, live band kicks out top-notch entertainment. When there's a lull, take advantage of some of the best soul and blues albums you can find in one place. Don't be afraid to try something you've never heard before…it's the best education you can get for a quarter or two.
Old Town Ale House
Hey, this place wasn't John Belushi's favorite hangout for nothing. Classic jazz, soul and blues will tell tales of the Windy City's musical history (rock and pop make the cut, too) as you sip on a beer or three and check out the mural featuring famous patrons like George Wendt and Bill Murray. If nothing else, you'll have a good Billie Holiday tune to hum as you stumble home at 5 a.m.
Got some more change? Check out the 'boxes at these bars:
Carol's Pub lets you create your own country soundtrack.
Zakopane rewards its regulars with a selection of obscure Polish rap and pop.
Delilah's will get you going during breaks from the awesome live acts.
Ravens is one of the few 4 a.m. bars that at least pretends to give its patrons credit for the tunes that sound so swell so late at night.
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