Cool city but not "better" or "worse" than New York, which it's always trying to compare itself to; despite the fact that there's no comparison. They're just different and they each have different charms and drawbacks.
New York rocks. Chicago rocks. End of story.

Cho cho cho, i heart chi-town, and NorthSide1983 need to take some Midol.
by Not a Chicagoan September 28, 2005
Get the chicago mug.
The best city in America and my “second home town!!” America’s 3rd largest urban area with almost 10 million people in 3 states (Illinois, Indiana and Wisconsin) along the southwest shore of Lake Michigan. It is a very large metro area that may not be as big as New York or Los Angeles, but is America’s largest inland city and more metropolitan in profile than the latter (at least Chicago has cleaner air and adequate public transportation unlike L.A.). Its most common nickname, “the windy city” actually has nothing to do with meteorology. Although windy (especially during its frigid winters when winds come off Lake Michigan), it stems from its boasting politicians in the 1800s during the world’s fair about the city’s greatness, which it no doubt has. It is the cultural, commercial and transportation center of the Midwest and is a very diverse city with a lot to offer: beaches, a huge lakefront, arts, museums, culture, shopping along Michigan Avenue, awesome architecture (the Sears Tower is among the tallest buildings in the world and the city is building the Chicago Spire, which will surpass Sears as the tallest building in the U.S.), Chicago Deep Dish Pizza, the Gold Coast Dog and one of the world’s busiest airports. The Chicago Metropolitan area contains over half of Illinois’ state population. Not surprisingly, Chicago has so many things to see and do: Navy Pier, shopping along Michigan Avenue, going to a ball game, visiting the Museum of Science and Industry, the Adler Planetarium, the Lincoln Park Zoo or the Brookfield Zoo, go swimming in polluted Lake Michigan (unless it’s the middle of a frigid winter) or going to Lake Geneva for the weekend. The worst thing about Chicago may be its gang problem (who doesn’t have gangs?) and extreme climate: hot and humid summers and frigid winters. Just try exposing yourself to the winds of Lake Michigan in January. If climate is the worst thing about Chicago then I’d say things are pretty good. New York can go screw itself. New Yorkers are fake and Chicagoans are real. Chicago over New York any day.
Chicago is the best large city in America!!
by krock1dk@yahoo.com September 4, 2007
Get the chicago mug.
A kickass jazzy group. Known for their laid back style of music. Potheads get high while they listen to it and rich brats listen to it while they snort their crack. It brings the people together.
Heh, put in that Chicago CD!
by rubywpnmaster June 16, 2004
Get the chicago mug.
A process by which some Midwestern cities, formerly sleepy towns, gain urbanization and become more like Chicago, Illinois.

Many long-time natives of these cities, and furthermore, those living in the same area but outside these cities, despise the process.
I'm sick of it... Indianapolis is getting chicagoized. A new downtown, mid-rise condo towers, and a gentrified hippie village... What's next, a 20 mile bike path? Oh, wait.
by Alan Kirschner June 16, 2007
Get the chicagoized mug.
OH HELL NO!
first of all how the hell can people keep saying chicago compares itself to new york..chicago is a damn city..not a person..it cant talk! and the people here do have good reason to comopare to new york. they both have terrible gang violence..and full of peoplpe on high-horses(less in da chi) and have big buildings. And never say were not educated..how arent we when most of the math books in the world come from chicago. and were the leading medical city in the country. and another thing!
1|chicago is better than ny...it just is all you have to do is talk to someonw..we wont shut u up or walk past you like those e yuppies
2|there is diversity..the only people who think we arent are outsiders
2|we arent racist...when me an my friends see white people downtown(being from the southside)we talk and both groups just wanna rep our city!
3|new york is full of wannabees while chicago produces some of the best most cultured people in the world.
before you dis chicago COME THE HELL OVER HERE!!
3|and our L system is cleaner,smarter,and more comfortable
oh...chicago i love your skyline
please help us chicago we need some of your water!-LA
IM FROM BROOKLYN!-NY
well i went to robeson high in south chicago and now i nake 7 figures...QUARTERLY!-chicago
by fred s. July 1, 2006
Get the chicago mug.
an 80s band that played both heart wrenching break-up songs and songs that almost guarantee sex. ex we can last forever and stay the night.
girl to friend's : I didn't want to at first but then he played some chicago and and I could not controll myself.
Get the chicago mug.
A pretty cool city. Better than the shithole(New York). A lot like another great city, Boston(which is the best in my opinion). Also, people from there aren't all arrogant assholes like New Yorker's are.
by AflacJack August 13, 2003
Get the chicago mug.