45 Percent,
I can see why you think Chicago isn't better if you mostly just hanged out in Chicago downtown and U of Chicago area.
First of all, Chicago downtown doesn't have the highest concentration of cafe and restaurants. I personally think Chicago downtown, other than being a finanical district, is best for touristy things, theater/art shows, shopping but not for just hanging out. But even if you just hanged out in the downtown, you should have felt it's a cleaner, richer (more wealth), and more well-managed city. The sheer size of downtown tells you Chicago is a more prominent city. In 2006, I got to know a group from London while there for 10 days. They were impressed.
U of Chicago is in the southside of Chicago. I've only been there once and it's supposed to be one of the better parts of the southside which as a whole is considered poorer than its northern counterpart. So you didn't really get to see the nicest parts of Chicago.
Image:Chicago community areas map.svg - Wikipedia, the free encyclopedia shows the neighborhoods of Chicago. I don't claim to know all about Chicago; I am mostly familiar with the lakefront neighborhoods north of the Loop because they are supposed to be the most happening and easily accessible by public transit (I didn't have a car). I'd say among them (excluding the downtown), the Near North, Lincoln Park, and Lakeview are far better than Center City. By better, I mean nicer looking, cleaner, and safer. Edgewater, and Uptown are not bad either. There are tons of restaurants and shops along streests like Clark, Halsted, and Broadway in those areas. If you use a google map, you'd see Near North, Lakeview, and Lincoln Park as a whole is a much bigger area than Center City/Old City and I am not even counting downtown Chicago (Loop). I don't know much about all the other Chicago neighborhoods.
I was in Philly last September. I stayed in Center City and I walked a lot in the area. I also walked from there to Chinatown. That Center City/Old City has 200-sidewalk cafes isn't really that impressive actually considering it includes just about any restaurants that have seats outside. I am a food lover and fairly particular with what I want. I was not impressed with the variety. There were very few Asian restaurants. As a point of reference, even thought Lakeview is pretty white, there were five Thai restaurants within walking distance from my hotel in Lakeview when I was there for my friend's 40th b-day in Feb and I am not even counting other Asian like Vietnames, Japanese..etc. Anyway, it took me a while to find a semi-decent looking sushi place in Center City but it turned out to be very mediocre. I did have a pleasant meal in a South American place. If I am not mistaken, Center City+Old City is considered the most vibrant area of Philly and it's really not that big. I don't think it takes more than 45 min to walk from west to east. I admit I don't know anything about areas outside of Center City and Old City. But I didn't bother to see other parts partly because of time constraint and partly because of this map I saw before my trip
The Philadelphia Inquirer . It kinda adviced me not to wander outside of CC.
