These side gigs will help you pay for beer, chips-and maybe even rent.
BEAT THE TAMALE GUY AT HIS OWN GAME. Sure, reselling another restaurant’s food to drunk people on the side of the road is sketchy and might violate some serious health codes, but it’s also a fast way to score cash. In an effort to see just how sweet the “Tamale Guy” has it, I headed to Wicker Park on a Friday night armed with a fresh pizza, an entrepreneurial spirit and a manila envelope reading pizza, $3/SLICE (OR BEST OFFER). As it turns out, you hardly need either spirit or a sign to make this moneymaking scheme work. Drunk people flock to fresh pizza like zombies to brains. I not only sold half in the first three blocks, but I had to mitigate a bidding war between two dudes who both “just fucking want[ed] some pizza.” The problem is that hot pizza has a short shelf life in Chicago’s Siberian temperatures, and the second half of my merch was harder to move. Eventually, I was forced to lower the price to $2 a slice, but in the end I made $14 in pure profit.
Prerequisites: Heat-trapping container, tolerance for drunks
TUTOR YOUR TESTEES. Overeducated unemployed people can make some scratch helping others on their way to becoming overeducated and unemployed. To tutor for Kaplan Test Prep (2828 N Clark St, 773-296-4113)—which starts at $20 an hour—you must have scored in the 90th percentile for the test you want to teach. (If you haven’t taken the test in five years, Kaplan administers a diagnostic exam. Scary!) However, “If a teacher can’t motivate, engage and enlighten students,” cautions Kaplan’s Carina Wong, “it doesn’t matter how high their test score is.”
Prerequisites: Brainiac-level smarts, ability to connect with students
GIVE GREAT VOICE. Chicago ad firms represent a bevy of major companies—McDonald’s, KFC, MillerCoors—which translates to commercial work that ranges from $250 for an ad on local radio to $20,000 for a national TV spot. “There’s no shortage of wannabes,” says Debby Kotzen, owner of talent agency Naked Voices (900 N Franklin St, 312-563-0136). What can put you over the top? “It’s all timing,” Kotzen says, “the ability to bring a script to life.”
Prerequisites: Sterling pipes, abundant personality
BUSK, BABY. The city’s vampiric fee-and-fine policy also applies to street performers—a $100 license is required to take your show onto sidewalks and El platforms. More unique or conceptual acts draw larger crowds and bring in more bucks, so don’t think you’re gonna get rich strumming Dave Matthews covers. On average, busker Jason Trusty’s traveling menagerie, Puppet Bike, brings in $75 in an evening, and a bucket-drumming brigade camped out along State Street or Michigan Avenue pulls down $150 to $200 a day. Plus, that Tin Man–Michael Jackson dude on the Mag Mile always seems to be raking in cash.
Prerequisites: Showmanship, license to rock
SPILL SEED. To be blunt: You’re gonna yank your crank anyway, so better your little soldiers end up in a lab cup than on your girlfriend’s good towels. After passing an exam that tests for infectious diseases and drugs, donors at Midwest Cryobank (4333 Main St, Downers Grove, 630-810-1201) squeeze out a couple dozen deposits—$25 each—over several months. Each donation room has extensive “inspirational” reading material (sorry, no vids).
Prerequisites: Healthy sperm count, willingness to whack
PUMP OUT PLASMA. You can’t spend a sugar cookie, so skip regular blood drives and donate plasma, the yellowy stuff blood cells are suspended in. To donate, bring a photo ID, Social Security card and a piece of mail to Interstate Blood Bank (3324 W Lawrence Ave, 773-478-2989). After a series of blood tests, you’ll get $20 to $30 for a single two- to three-hour session.
Prerequisites: Healthy lifestyle, love of needles
GET SCRAPPY. You’ve seen those pickup trucks overflowing with junk puttering around town and surely wondered, Is that guy crazy? Yeah, crazy like a fox! Garbage fishermen can get quick cash for a significant haul at yards such as South Chicago Iron & Metal (1313 W 74th St, 773-488-1313), which offers 10 cents per pound of any metal.
Prerequisites: Unbelievably beat-up Ford, tetanus shot
TEST YOUR HAIR METTLE. If you’re still maintaining that Tawny Kitaen-in-a-Whitesnake-video ’do, why not profit from a long-overdue haircut? Post pics and a description on sites like thehairtrader.com and hairwork.com, and wigmakers may bid on your mop. The longer and more exotic your mane, the better. Twenty-one inches of never-dyed red hair recently fetched $1,000.
Prerequisites: Long locks, willingness to part with them
CRAFT THRIFT-STORE TREASURES. Sara Bradstreet, owner of Broad Street jewelry, bargain hunts for vintage jewels, refashions them into new pieces and sells them online as well as at Pivot Boutique (1101 W Fulton Mkt, 312-243-4754) and Wolfbait & B-girls (3131 W Logan Blvd, 312-698-8685) for $30 to $120 a pop. Thanks to eBay and Craigslist, an opportunity to hawk what used to be junk is only a click away.
Prerequisites: An eye for potential, keen refurbishing skills