25 Reasons Why Chicago Is The Most Underrated City In America

Here are 25 reasons why Chicago is America’s most underrated city:

  • The Cost of Rent: It’s no secret rent in New York and San Francisco costs a ton for borderline poverty conditions. It is a secret that in Chicago rent is dirt cheap for extravagant buildings. Statistically median gross rent is $1086 in NY vs. $886 in Chicago, but the money goes significantly further. Not only do renters not pay the brokers fee in Chicago, they can expect to find a range of options from houses in Lincoln Park to Condo buildings with pools, tennis courts and gyms. There certainly are not Tumblr accounts dedicated to crazy rent prices in Chicago.>
  • It’s also cheaper to buy: The Legacy Building, one of the nicest and newest buildings on Millennium Park in Chicago, is priced at on average $600 per square foot. The average for the new 432 Park Avenue building in New York is $6,000 per square foot.
  • Don’t think that it’s just a demand issue either. Building in New York is significantly more difficult and expensive, with more onerous zoning laws, rent control, and union laws for hired workers. Most people think they are getting what they pay for, in reality they are paying an enormous phantom tax as a result of the regulatory regime. In Chicago, when prices rise, building increases.

Millenium Park

  • It’s not just prices of real estate that are different, moving from Chicago to New York means your groceries prices rise 30% (and to add salt to that wound, there are fewer Trader Joes in New York despite the higher population), your utilities rise 47% and your health care costs rise 20%.
  • In Chicago, when you leave your building, you’ll notice the streets are clean. This is because there are alleys, so no garbage is left on the street ever.
  • Chicago’s layout makes sense. It had the luxury of “resetting” in 1871 after a fire burnt everything down (17,500 buildings leaving 1/3 of the city homeless). Daniel Burnham’s ‘The Plan of Chicago’ provided a guiding vision.
  • Burnham’s goals included every citizen being walking distance from the park – today there are plenty – Grant Park, Millennium Park, Lincoln Park, Portage Park and Jefferson Park. Chicago’s parks are bigger than New York’s even though they are located right in the heart of the city, and its largest one is significantly bigger (Lincoln Park is 50% larger than Central Park). Burnham also designed the roads to be wider after the fire, which included a widening of Michigan Avenue, Roosevelt Road and the creation of Wacker Drive. This helps with increasing direct sunlight.
  • Wider streets also help mitigate the crowding of the many large buildings. Of the tallest 10 buildings in North America, Chicago has four (NY has five). Of the tallest 20, Chicago has 7, New York has 6. Of the tallest 40, Chicago has 12, New York has 11. New York does have more tall buildings in general, but for Chicago’s population, it carries its weight.
  • Those tall buildings are the home to a lot of companies, with jobs in industries such as Consulting, Banking, Venture Capital, Private Equity, Insurance, and a whole host of industries that actually “make things”. But know that when you are out at night in Chicago, people don’t tend to care as much where you work or how much money you make.

Oak Street Beach

  • Burnham also proposed a cultural center in the park that the city would be built around. Today this space includes the Field Museum, Art Institute, Adler Planetarium, the Shed Aquarium, and Soldier Field, home of the Bears.
  • Speaking of Sports complexes, all of Chicago’s teams play within the city, and all are within 15 minutes of the Loop (Wrigley Field, United Center, Soldier Field, U.S. Cellular Field).
  • Chicago has beautiful beaches, of 29 miles of beach in the city, all but four of which are public parkland. From an office buildingon Michigan Avenue, you’re no more than a few minutes’ walk from Oak Street Beach.
  • You can also swim at these beaches. Lake Michigan has crystal clear waters that can be visually confused for the Bahamas (although they are not as warm).
  • From an office downtown, you also can be on a golf course within 15 minutes. The Sydney Marovitz 9 hole course on the water is right across from Lincoln Park. Chicago has a number of excellent public courses available.
  • Chicago’s airports are also easily accessible from the city, with straight shots on the EL: 25 minutes from downtown for Midway, 45 for O’Hare.
  • And with its convenient central location, you are a two hour flight from Colorado and New York, and only four hours from California.
  • Chicago has relatively low taxes for a big city. The sales tax is high at 10.25%, but there is no personal income tax in the city.
  • Not only is the average commute shorter (35 minutes vs. 40 minutes), there are fewer people having to deal with this.
  • Chicago is a culturally rich city whose rivers are only ever Green on purpose. Beyond St. Patrick’s day there are a number of city festivals, both large like Lollapallooza and smaller like Christkindlmarket, a miniature Octoberfest in the heart of the loop in the winter. Of course there are numerous actual Octoberfest celebrations as well.
  • There is also a sizable theater scene and the famed Second City.
  • And a huge restaurant scene that isn’t very expensive
  • Chicago also has a fun yet unpretentious night scene. If you want long lines and the “models and bottles” crowd, proceed to Paris Club or return to LA/New York/Miami. If you’re in for music, late night bars and dancing then staples such as the Hangge-Uppe, Butch McGuires, or Stanley’s.
  • Perhaps the best thing about Chicagoans is their modesty. Northwestern University President Schapiro, himself an east coast native and former President of Williams College, described it: “I love the civility, I love the humility, I love therespect, I love the friendliness, I love the lack of entitlement.”
  • Speaking of Northwestern, Chicago has two excellent Universities with strong graduate schools as well; providing the city with a constant stream of new talent.