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Chicago has been called “New York done right.” Indeed, the city of about three million has much of the Big Apple’s culture, breathtaking views and big-city amenities, minus the attitude. Chi-Town embraces newcomers, so keep safety in mind as you would in any metropolis, but dive right into the dating scene. Here are 10 pointers to keep in mind.
1) Budget your fun
Avoid high-rolling parts of town like Lincoln Park and Evanston, and instead take in some culture on the cheap. Head to Pilsen for a free visit to the colorful National Museum of Mexican Art, or hold hands one night through Jefferson Park, just northwest of downtown, and take in the spectacular cityscape. Artsy types should browse the records and vintage clothing in Wicker Park. Depending on the part of town you’re in, you could have a decent evening for two for under $75.
2) Dress Comfortably
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3) Take the L.
Chicago’s elevated train system covers 222 miles of track, so ditch the car — and the futile search for parking — and invest in a Chicago Transit Authority pass. Chi-Town’s Midwestern friendliness makes it okay to ask that cute stranger about the book he’s reading or find out which train stop to take. You can access most parts of town within an hour.
4) Have a Sense of Humor
In the Windy City, everyone’s a comedian. Tickets for the famed Second City comedy show average about $20 each, but you can also catch stand-up acts and even improv puppet troupes for as little as $5. And here, a sense of humor goes beyond the clubs. When a stranger hits on you, retort with a quick-witted zinger, and you can both smile as you go your separate ways.
5) Get Caught Reading
What better conversation starter than the celeb photos in RedEye or the latest Michael Crichton novel? Chicagoans are unpretentious, but they’re also academics at heart. Settle in with some reading material on the L, or spread out a blanket and read in the sunshine at Millennium Park.
6) Walk it Out
Chicagoans are a hearty bunch. If your date wants to take a bus to Bucktown and then split a turtle sundae at Margie’s Candies, don’t write him off. A great way to weed out the down-to-earth types from the snobs is to see who’s comfortable walking or taking Chicago’s perfectly adequate public transportation system, and who insists on a private car. Of course, cabs are your safest bet at night. The meter starts at $2.25, and then increases 20 cents for each additional ninth of a mile.
7) Eat with Gusto
When Chicagoans aren’t eating, they’re planning their next meal. This is not the place to be coy by ordering a salad. Dig into deep-dish pizza, try spinach pie in Greek Town or sample delicacies along Michigan Avenue during the Chicago Chocolate Tour.
8) Work up a Sweat
People here play hard, but they also work out hard, too. You’ll find gyms even in the less-than-swanky neighbors, so get moving.
9) Get Sporty
Chi-Town’s sports fans are notoriously rabid — er, passionate — so if you’re looking to join the brouhaha, check out a professional team. Die-hard Bears fans brave the elements to cheer on their football team in the bitter cold. With two Major League Baseball teams — the Cubs on the north side and White Sox on the south side — America’s favorite pastime can be as polarizing as politics. And even when the Bulls are mediocre, you’ll spot a celebrity or two in the crowd of basketball fans.
10) Jazz it Up
Chicagoans are spoiled when it comes to music, with jazz A-listers like saxophonist Branford Marsalis, vocalist Cassandra Wilson and pianist Ramsey Lewis playing frequently. For great value, try an unassuming dive bar. Green Mill Cocktail Lounge on the Far North Side is a softly hit watering hold that was once a hangout of mobster Al Capone. Admission is usually under $10.
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