Well I am from Chicago...I am proud to say that I am!
Good Points:
-So many things to do! Downtown always has things going on and the ourskirts of downtown have alot of fun places to go to for the entire family (e.g. Navy Pier, Field Museum, Sears Tower, John Hancock).
-Good eating! Chicago is very diverse and it's reflected in our diet
We have food ranging from Soul Food, Mexican, Indian, Greek, Italian (DEEP DISH IS THE CITY'S DISH), Chinese, Ethiopian, Nigerian, Russian, Puerto Rican, Colombian, Polish and many more
-Very Diverse! The neighborhood where my school is located (Rogers Park) is one of the most diverse neighborhoods in the nation, you can find pretty much everyone from everywhere here!
-Various cultural institutions! Being that Chicago has one of the largest Black populations in the country, it is not too difficult to find some culture in the city from the DuSable Museum of African American History, RAINBOW/PUSH Coalition, Nation Of Islam, Bronzeville, Chatham, Hyde Park, Kenwood, South Shore and Harvey, IL. Chicago is also home to one of the largest Mexican populations in the world, so again you can find alot of culture in the neighborhoods of Pilsen, Little Village, Back of the Yards, the SW Side, and museums like the Mexican Fine Arts Center Museum, Museum of Mexican American culture, the art galleries in Pilsen and Little Village.
Bad Points:
-Very Segregated. Chicago, I believe, is the #1 Metropolis in regards to segregation. It is also very overt (tracks/viaducts/parks), so you can easily see who lives where. The "El" line services also reflect the disparities as there are more stops and frequent service in public transportation among richer, predominantly white neighborhoods than in poorer, Black neighborhoods (even a Black Middle Class Neighborhood like Chatham doesn't get great service compared to the North Side neighborhoods of Wrigleyville, Boystown, and Lincoln Park).
-HORRIBLE PUBLIC TRANSPORTATION. While we are lucky compared to other cities, the service can be better! A good amount of the city takes public transportation but the same woes arise regarding construction, frequency, late arrivals/departures, and disparities among neighborhoods as mentioned before, lack of public transportation in depressed neighborhoods only contributes to degression of these neighborhoods as it is the only means of getting to work, since there are little to no jobs in the neighborhood.
-Politics, Dirty Politics. Things ranging from Gentrification, corruption in city hall, police activity, are still alive in my city. The one that hits closest to home is Gentrification as "Da Mare" is quickly pushing out low income folks (dominantly of color), out to the burbs by approving the building of condos and townhomes in their neighborhoods, it seems as a new shift is occuring where more residents of color are being pushed out of the inner city and moved to the inner ring suburbs and outskirts of the city, and more suburbanites are moving into the inner city.