Summertime in Chicago means the bars will be as packed as ever with young singles looking to mingle and tingle. The women of this city are as distinct as the neighborhoods that produce them, and it's important for every guy to know his environment. Below is a handy guide to help a young bachelor navigate the waters of some different neighborhoods, with my researched-albeit extremely biased-recommendation for the perfect drink to order a lady in each one.
Gold Coast: Scotch
How did you even end up in the Triangle? She's old enough to be your aunt, and they're clearly fake. Quit trying to outkick your coverage and head up to McFadden's.
Lincoln Park: Bomb
O-bomb, car-bomb, Jager bomb. She might look like the bomb, but she's three quarters of the way toward getting bombed (don't read this out loud on an airplane). Chances are high that she goes to DePaul, and you probably can't compete with the guy who lives in her dorm. Sorry, champ.
Loop: Happy hour beer
She's a busy working professional and she only has time for one drink because she has to get to her spin class. While she's grateful for the gesture, don't break your wallet; you'll always come second to her career. I'd stay in touch with her in case you ever need legal advice. Which you will, because it's summertime in Chicago.
Old Town: Martini
Her friends told her they were going to Old Town Social so she busted out the stilts. You can find her leaning against the bar for support, her legs wobbling on her heels. Despite the fact that she seems a little out of place, she'll definitely know what type of vermouth to order in her drink.
River North: Vodka soda
Simple, classic, affordable. And I'm not talking about the drink. Be careful, you might end up having to buy a round for the rest of the bachelorette party she's with, but most of them seem like decent human beings. Bail if she says the words, "I want to go to a piano bar!"
Streeterville: ?
I can't find a bar anywhere. All I see are apartment buildings. Is it shady to try to buy a girl a drink at Lucky Strike? Is that a thing? A Beer and a bowl? I'm making it my thing. If it doesn't work out, I can always see "Iron Man 3" by myself again at AMC.
Wicker Park: PBR
The good news: It's cheap and easy for the both of you to get buzzed. The bad news: You don't have any tattoos or a handlebar mustache, so you feel out of place. Don't go back to her place if you're allergic to cats. Also, how do I get to the Red Line from here?
Wrigleyville: Doesn't matter
It really doesn't.
John Hickey is a RedEye special contributor.
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