Rogers Park

The coolest neighborhood in Chicago, mostly due to the diversity, proximity to Evanston, and all the cool former members of the Lutheran Volunteer Corps living in the area. Unfortunately, there's a lot of gentrification going on in the area, as old 3-flats are being taken over by condo developers. Still, there are a lot of cool peoples around.

(updated 19.12.2000: OK, calling it the coolest neighborhood was a bit subjective, I admit, but hey, it's my hood - what can I say?)

Absolutely NOT the coolest neighborhood in Chicago, although aarestad is right about the rest. I can think of about five neighborhoods of equal diversity that a random sample of miscellaneous Chicago residents would probably consider more 'cool', although there are some noteworthy places worth checking out in Rogers Park.
The Heartland Cafe has great food and often supports good bands. Exit Cafe is a much teenier spot down the street from the Heartland where smaller, more beatnik-like bands perform and there are always interesting people sitting around with whom one can play checkers, cards or penta.
The Morseland is kind of nifty; its like a club but smaller, like a bar but darker and louder, and where my friend DJ's each Sunday.
Loyola University is in Rogers Park, lending to a large amount of college-age people and the usual coffee houses and shops that accompany them. One amazing thing about Rogers Park is the fact that, despite the gentrification that has started there, one can still find a good-sized apartment for very cheap rent.

More things that make Rogers Park worth living in:

Enormous housing diversity, including massive houses, bungalows, 3+1s, tenements, high-rises (along the lake), and tons of two-flats and three-flats.

Enormous human diversity, with large concentrations of students AND old-folks-homes...first-generation Mexican immigrants AND Irish sixth-generation Chicago families...the Sun Myung Moon unification church AND a Hare Krishna temple...(hrm, well, anyway it emphasizes the diversity.) Devon Avenue ties (loosely) together Indians, Pakistanis, Hasidim, Assyrians, and many others all in the space of about two miles.

Enormous open space availability compared with most of the city...including Pottawattomie, Touhy, Loyola, and Warren parks... and Indian Boundary Park (and zoo!) Not to mention a beach at the end of nearly every east-west street.

Enormous public transit infrastructure: Between the Howard Street CTA terminal and the local Metra rail station there are express and local options on bus, light rail and train services.

Rogers Park has a decidedly boho charm. Nonetheless, it is undoubtedly one of the ten worst neighborhoods in Chicago, though this applies mostly to the North and East portions. Enrollment at Loyola has been sharply dropping because of recent serial rapists and general sketchiness. I say this to you: do not get off at the Morse stop after 10 at night. You'd probably be fine, but I've had more than a few friends who've had unpleasant incidents.

On the other hand, if you're thinking of buying a condo, Rogers Park is a good bet. They're going for a song, and it's only a matter of time until the neighborhoods get cleaned up.

Visit Cafe Ennui, Don's Coffee Shop and the afore mentioned Heartland Cafe.

Having spent plenty of time in Rogers Park in the last five years and living in nearby Edgewater a few years back I had to add my few cents.

First of all, most of Rogers Park is unsafe, especially at night and even more so if your white. Unless you goto school at Loyola or need to visit someone there, I'd advise most people against ever going there although you can get a real unique taste of Chicago there during the day.

I think this area is most noted for it's hard to find parking, dense population, ghetto beaches, brownstones, and Loyola of course.

Venture down Devon Ave. west of the lake and you'll get to see (and experience if you get out and walk around a bit) one of Chicago's most interesting Indian enclaves. There might just one be the largest concentrations of currency exchanges in the city outside of the loop as well!

There has been some new development going on in the area and some effort is being made to gentrify certain blocks. It's still a great place to see some real urban blight near Howard St. But note, as soon as you get into Evanston, everything changes for the better.

Seriously though, if your white and don't want to be mugged and or attacked for being white, avoid the streets of Rogers Park at night... and those nearer toward Howard during the day even.