Introduction to Chicago : 18 Things We Love and 7 We Don’t

Sweet home, Chicago. As an eight-year resident of this enigmatic city, we have had quite a tumultuous relationship. Cyclically, I am flooded with feelings of love, hate, joy, anger, contentment, and disdain (sometimes in the same day). Unsurprisingly, these roller coasters of emotion typically coincide with the seasons. No, I’m not bipolar: I live in Chicago. Through the doldrums of winter (particularly during the recent polar vortexes), and sometimes spring, I desperately look for anyway, or flight, out. But, those glorious, sunny, albeit rare, days make me fall in love all over again. And I ponder, what city could really compare? This is why we remain Chicagoans, right?:

“Loving Chicago is like loving a woman with a broken nose, you may well find lovelier lovelies. But never a lovely so real.” –Nelson Algren

The Food

No, I am not referring to Chicago hot dogs or deep dish pizza. [Neither of which I love… *turns in Chicago card*] Or the fresh seafood (we are in the Midwest). From high-end, Michelin-starred restaurants- Grant Achatz’s Alinea has recently named the top restaurant in the country and among the top in the world- to tasty, cheap, holes-in-the-wall, Chicago has a culinary scene that, IMO, rivals that of New York and San Francisco. Chicago is a melting pot of ethnic enclaves and can readily satisfy whatever eclectic cuisine you are craving.

The People. Relatively speaking for a big city, and in true Midwestern fashion, Chicagoans are an affable, unpretentious bunch. Having lived in Washington, DC, Chicagoans are seemingly the friendliest folks on earth. But I digress.

The Central Location

Close proximity to two major airports and a central geographic location makes flying just about anywhere in the US of A easily accessible.

The Neighborhoods

A city of neighborhoods, Chicago lends itself to seemingly endless exploration. Each hood has its own distinct crowd, venues, and vibe, and there’s something for everyone.

The Watering Holes (And Corner Bars)

Chicago is a veritable drinker’s utopia. Cocktail bars, wine bars, dive bars, breweries, blues bars, nightclubs, and lounges abound in this imbiber’s paradise. This was recently confirmed by GQ Magazine which proclaimed Chicago America’s Best Drinking City. And really, what is more classically Chicago than the ubiquitous Chicago neighborhood, corner bar filled with friendly, tippling locals?

The Lakefront

Chicago’s Lake Michigan shoreline enjoys 26 miles of public beaches, a scenic 18-mile lakefront trail, expanses of green park, picturesque harbors, tranquil nature preserves, and recreation areas including tennis courts, a golf course, soccer fields, and volleyball courts.

The Summer (And Fall). Summer

when the city comes alive and the reason the majority of Chicagoans endure ghastly winters. Fall: when the air is fresh and crisp and the trees are awash in a kaleidoscope of color.

The Street Festivals

Chicago boasts a dizzying array of neighborhood festivals, street festivals, ethnic festivals, art festivals and music festivals (many of which are gratis), especially in the summertime.

The Architecture

Chicago is home to famous architects, world-renowned, iconic architecture and is the birthplace of the skyscraper. The Sears Tower (Chicagoans are hard-pressed to embrace the Willis Tower) was the long-time, the tallest building in North America until the completion of One World Trade Center in NYC.

History. Chicago is a city rich in history from the World’s Fair and Columbian Exposition to the Great Fire and the city’s rebirth to the lawless era of prohibition and organized crime (ahem, Al Capone).

That Breathtaking, Unmistakable Skyline.

Public Transportation

As much as people gripe about the CTA (Chicago Transit Authority)- and for as many instances of inexplicably bad smells as one may encounter riding the L- Chicago is fortunate to have elevated trains, subways, and buses to make the city accessible. And depending on where you reside, having a car is optional.

The Walkability

Chicago ranked as #6 in Walk Score’s 2014 Most Walkable U.S. Cities Ranking. Okay, okay, the walkability-factor may diminish in those windy, bitterly cold months. But, see #12.

The Affordability

Chicago is cheaper than most (if not all) large, metro areas in the U.S. that offer what Chicago has to offer. Rent-wise and real estate-wise.
The Museums. Chicago has a renowned collection of museums including the Museum of Contemporary Art, the Field Museum, the Museum of Science and Industry, the Adler Planetarium, the Shedd Aquarium, and of course the Art Institute of Chicago– which recently earned the accolade of Trip Advisor Traveler’s Choice Award Winner for the best museum in the WORLD in 2014.

The Parks

Chicago’s motto is urbs in horto: Latin for “City in a Garden.” Chicago has no shortage of green areas. Lincoln Park along the Lakefront- Chicago’s version of Central Park; Millennium Park (home to the infamous “Bean”); Grant Park; Humboldt Park; Garfield Park; Jackson Park, just to name a few.

The (relative) Cleanliness

I’ve heard numerous visitors to Chicago marvel at how clean it is. Unlike some cities, Chicago has alleys with dumpsters (which helps).

Greektown. Okay, I am likely biased, but Chicago is one of the few American cities with a vibrant Greektown. Greektown houses the National Hellenic Museum and is the birthplace of both the gyro and that irresistible flaming cheese, saganaki (OPA!).

7 Things to Dislike about Chicago

  1. The Weather/Climate. Whipping wind, freezing, sub-zero temperatures, snowy, gloomy, miserable depressing weather. Potentially for months on end. Some say it builds ‘character.’ Others say it makes Chicagoans insane masochists. A catalyst for my wanderlust, and ultimately the impetus for a potential move to a sunnier, toastier locale.
  2. The Taxes. They are steep- on sales (9.25%), property, and income.
  3. The Gas Prices. Chicago has some of the highest gas prices in the nation.
  4. The Segregation. Chicago remains one of the most racially-segregated cities in America.
  5. The Crime. It’s no secret Chicago is plagued with violent crime and gangs. Hence, the unseemly #chiraq.
  6. The Corruption (read: Politics). Machine and pay-to-play politics are alive and well in Chicago. Oh, and 4 of our last 7 governors went to federal prison.
  7. The Location. Chicago’s central Midwest location, situated in the midst of the “fly-over” states, arguably cuts both ways.


Leave a Comment