Lots to do in Chicago. I had a week there i didn't want to leave. Not sure what you consider a cool neighborhood, my idea of a cool neighborhood is one that is gay friendly
One place that makes a perfect day trip if you're a Frank Lloyd Wright fan is Oak Park Illinois. It's about a 20 to 30 min ride on the green subway line. You can tour Frank Lloyd Wright's home and studio, as well as a walking tour of the neighborhood looking and learning about the history of the mansions he designed, Oak Park made the perfect day trip! even though the subway goes through some of Chicago's ghetto it is perfectly safe during the day.
Another area worth checking out is Wicker Park, mostly shopping boutiques bistros coffee shops and hipsters if you're into that sort of thing. ,Andersonville is another similar area and is very gay friendly.
As already posted a architecture boat tour is a must!!!
http://caf.architecture.org/page.aspx?pid=574
Lincoln Park has a beautiful zoo and best of all its
FREE it's better than most zoo's that charge admission! I spend my last day in Chicago hanging out in Lincoln Park and the near by Oak beach.
PinkLucy When i visit Chicago i like hotels to be close to fine dining and shopping so i try to stay in the gold cost area, not sure what you're budget is but the Residence Inn Chicago Downtown is a great place, it's one block from the Magnificent Mile, All rooms come with breakfast buffet and Monday to i think Thursday free beer and wine and light meal during the hours of 5 :30 to 7 :00 pm Chicago has tons of hotels with all different price points, If you want a room with a view check out the Four Seasons or Trump Tower. I had dinner at the Four Seasons we got table by the window over looking the street and lake and the food was incredible i highly recommend a meal at the Four Seasons!
http://www.marriott.com/hotels/travel/chird-residence-inn-chicago-downtown-magnificent-mile/
Hilton Suites another great hotel.
http://www1.hilton.com/en_US/hi/hot...es-Chicago-Magnificent-Mile-Illinois/index.do
I stayed here a few years ago
http://www.chicagoraffaello.com/ I had a suite, it was roomy not sure how big the studio's are.