Fodor’s, Frommer's, Rough Guide, Lonely Planet: just about every guidebook will tell you how to safely blend in in a foreign country – even if it’s just so you don’t get caught in a pickpocket’s crosshairs. It’s not life- or wallet-saving to look like a native in Chicago, but it will save you some embarrassment, which is pretty much just as important. Here are some fool-proof ways to look like a legit Windy Cityzen (see what happened there?)…
1. Memorize "Chelsea Dagger," and hum it wherever you go. Not only is this one of the best songs in the world anyway, but it is the game song of the Blackhawks, Chicago’s hockey team. Be prepared for people to randomly shout, “Yeah, Hawks!” at you, especially during the season.
Take it a step further: Wear a Hawks t-shirt or jersey, of course.
2. Complain about the CTA, loudly and all the time. The term “CTA” encompasses both the bus and the train (don’t call the latter the “L”; you’ll seem like a total townie), so there’s lots of material. After all, no one likes public transit, except Londoners, who pretty much rep the Underground because they don’t have a real sports team.
Take it a step further: Sigh long-sufferingly and observe how this trip would be so much faster on your bike.
3. Don’t go asking around for all to hear where the best deep dish pizza is. That’s like going to New York and…well, asking where the best pizza is. It is the quickest way to identify yourself as a tourist, unless you’ve already had to have someone direct you to the Sears/Willis Tower (in which case you might as well be wearing a Hawaiian-print shirt, khaki shorts, and carrying an old-fashioned Kodak around your neck). Here, the best pie is at Lou Malnati’s. As Barney Stinson would say: “So just…okay?”
Take it a step further: Try to contain your ecstasy when you take your first bite.
4. Know the villages and street slang:
"Viagra Triangle": Roughly outlined by the intersections of State, Rush, and Delaware, it is so christened because this is where men whose drinks are stiffer than their – ah, cocktails – take out twenty-somethings who use the phrase “sugar daddy” without a trace of irony. Trendy and expensive, but potentially worth its price in people-watching.
"Boystown": Primarily East Lakeview, but stretching west toward Roscoe Village, this where most of the gay community resides. Predictably, it’s a pretty damn cool neighborhood: unique shops and restaurants, great bars and clubs, and more laid-back than the Loop – think Greenwich Village versus Times Square.
"The Loop": Contrary to popular belief, this is not all of downtown Chicago. It specifically refers to the area delineated by the rectangular intersection of several train lines. It is defined by Wacker Drive and the Chicago River on the north and west sides, the lake front on the east, and West Roosevelt Road on the South. You can check off nearly all the attractions on your top ten list here.
"Wrigleyville": The area surrounding Wrigley Field, mainly bars and restaurants. It’s more or less like a fraternity decided to franchise, because why have just a one sloppy house of bros when you could have a whole neighborhood of them? (That being said, it’s great fun, and where you’ll find the best bang for your booze buck.)
Take it a step further: Learn River North, Ukrainian Village, Lincoln Park, Chinatown, Bucktown, Streeterville, Wicker Park, and Old Town. Speaking of...
5. Have an imaginary friend in Wicker Park. Seriously, everyone has a friend in Wicker Park.
Take it a step further: Have a friend who lives in Avalon Park. Hardly anyone has a friend in Avalon Park.
Lastly, a few ways in which it is totally acceptable to be an unabashed tourist:
1. Garrett’s Popcorn. That’s right, go stand in that blocks-long line. Because if this popcorn had a theme song, it would be Nicki Manaj’s “I’m Legit.” It has more street cred than a gang member from West Side Story.
2. Take a picture of yourself reflected in the Bean. Never has there been a sculpture so simultaneously ludicrous and majestic, and looking into it combines the zany gratification of a fun-house mirror with the sneaking suspicion that some grand metaphorical reflection is going on too. There’s probably a statistic somewhere revealing that a significant number of people have realized their life’s purpose while gazing into the Bean. Probably.
3. Ride the Navy Pier ferris wheel. Because seeing Lake Michigan, on a sunny day, from the top of the world...well, that never gets old.
So go ahead, gaze with wide-eyed wonder. Just do it from behind reflective sunglasses...figuratively speaking, of course. After all, the only thing worse than being that tourist is, well, just being a douche.
So you can un-pop that collar while you're at it.