I go on dates with Chicago. Mostly to eat.

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Chicago is my boyfriend

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Chicago Humor | Humor

Humor | Chicago Humor

The 14 runners you'll see on the lakefront path in Chicago

Whether you're a running newbie or training for the Chicago Marathon, you're sure to encounter these runners on the road to shin splints

Humor | Chicago Humor

Facing Our Fears: Chicagoist's Worst City Nightmares: Chicagoist

Chicago is wonderful, but today we share some of our worst city-specific nightmares we dread becoming a reality.

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    The most impressive and regrettable Chicago tattoos

    From hot dogs to Bears signatures, we take a peek at some of the most magnificent and revolting body art inspired by the city.

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      The 12 best Saturday Night Live sketches about Chicago

      From cheezborgers and the Blues Brothers to Dyke & Fats, SNL has long used Chicago inspirations for its sketches. We ranked the funniest.

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      33 reasons Chicago kicks New York's ass

      Of course Chicago is better than New York. We Chicagoans know this to be true and, if New Yorkers are being honest with themselves, they know it, too. So, once...

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      JUDGMENTAL MAPS : Chicago

      Post anything (from anywhere!), customize everything, and find and follow what you love. Create your own Tumblr blog today.

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      23 things we learned about Chicago from the movies

      The landscape and lifestyle of Chicago is a little suspect in the eyes of Hollywood. Here are things we learned about our CTA, sex lives and more from movies.

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      51 things you'll never hear a Chicagoan say

      Utter any of these sentences in public and risk being called out as a faux Chicagoan. Consider yourself warned.

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      The 15 best fictional Chicagoans of all time, ranked

      Ferris Bueller is No. 1 right? Ohhhh, what about Balki? Urkel?? See where your favorite Chicago characters rank.

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        How Chicago sees the Midwest, how the Midwest views Chicago

        Our map of state stereotypes breaks down how we in the city view our region. Yes, it's largely corn and pigskin. But just imagine what New York thinks of us.