Chicago: A Love/Hate Relationship

At this time of year when the air turns cold and the sky turns a flat, ugly gray, I always wonder, why do I live in Chicago and not in say, Barbados? As with anything in life, there is a good and bad side to everything, including the Second City. Here are 5 reasons why I love Chicago and it's environs, and 5 reasons why I hate it.

1. June, July and August
Bright blue skies, 80 degree temps. Summer in Chicago beats summer just about anywhere. Get out your grill, throw on some fresh corn and toss back your beer of choice.

2. You want culture? We've got culture.
World class museums, art fairs, Jazz Fest, Blues Fest, Gospel Fest, we have a museum or a Fest for just about anything.

3. Scenic Beauty
Chicago has a great skyline and a picturesque, sparkling lake front where you can walk, bike, swim, and generally escape the concrete jungle.

4. Food
We have everything from fancy pants restaurants fronted by celebrity chefs to the best Italian Beef and pizza in the world. Johnnie's beats Al's, Portillo's and everything in between.

5. Semi Affordable Housing
After college I
lived in a very nice 2 bedroom apartment in good location with one
roommate. My share of the rent was $500. That apartment in NYC or San
Francisco would have cost me twice as much.

1. January, February, and March
The ugliest months of all. Cold, dreary, snowy, boring, and depressing.

2. Traffic and Construction
I have three words for you that will make any Chicagoan shudder: The Hillside Strangler. I mean really, there is nothing anyone can do about this? Getting from any suburb to the city is usually a big pain in the ass and takes hours out of your day.

3. Sports
Chicagoans really love their sports teams, whether they are up or down, good or bad. I personally have no interest in sports and for the life of me cannot bring myself to care about the Cubs, Sox, Bears or Hawks. Whenever people discuss sports in my presence I simply nod and pretend to understand what they are talking about.

4. The Accent
Let's face it, if you live in Northern Illinois, you have that flat, nasally Chicago accent. I once worked for a company that sent me to San Francisco for some training. A woman said to me, "You must be from Chicago, because you have That Accent." I felt like I must have sounded like Chris Farley in the SNL Bears skit.

5. Snooty People
I have spent time in a lot of cities, especially New York. I have to say that Chicagoans are the least friendly, which is probably the opposite of what most people would think. People in Wicker Park with their skinny jeans, ugly 80's fashions and snotty attitudes really bug me. Sorry, I don't see a lot of down home Midwestern friendliness around here.

Ok, there you have it. Why I both love and loathe Chicago. Maybe if I get to Barbados enough times I can write a similar piece on that.

What do you love/hate about where you live?


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  • How about the Sub Tender in Forest Park? butter garlic fries, YUM!

  • I'll take September through May in Chicago any day over the hot, humid summers!

    I say: if you don't like the traffic and construction, then don't drive! I haven't had a car or a drivers license since 1991. One thing that irks me about Chicago is the enormous number of drivers, when there are such great public transportation options, and plentiful cabs. And because of this, Chicago is a hard city in which to be a pedestrian (especially when we are in a situation where we have the walk sign and drivers nearly run us over turning, which happens almost daily to me).

    I agree with you about the snootiness! I find it much easier to strike up conversations with strangers in New York or San Francisco than in Chicago.

  • In reply to karbon69:

    Thanks for your input! It's definitely better not to have a car if you live in the city. Public transportation isn't perfect, but it's easier to deal with I think.

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