What long boulevard or street is best for seeing true neighborhoods Chicago on foot? (non Touristy stuff) (Lexington: bus, trendy)

[emathias]

There are a number of different options, depending on what you want to see and how pedestrian-oriented you want the street to be. Western definitely runs through a broad cross-section of both gentrified and non-gentrified areas and probably does cross through the broadest swath of what Chicago has to offer. However, most of Western is terrible for walking. It would make a nice drive, or an interesting bus ride where you hopped off at a few points, but there aren't many sections that are really a great walk.

A more pedestrian-oriented street with a similar role in Chicago is Halsted. Start at Clarendon and Montrose (Clarendon turns into Halsted) and walk south. You'll go through partly gentrified Uptown, fully gentrified Lakeview and Lincoln Park, the edge of the torn-down part of Cabrini-Green, the industrial Goose Island and Fulton River districts, Greektown/West Loop, UIC, brand-new University Village, partially gentrified East Pilsen, a little industrial section south of that, then Quarry Park and into Bridgeport, which is mostly stable with a growing influence from Chinatown, partly gentrified, partly not. I wouldn't go south of Pershing, but if you wanted to you'd see things change for the worse and see some of the harder sections of Chicago, sections that have been hard for a very long time. That's a roughly 10 mile walk.

I think that walking on Milwaukee from Division to Belmont would be interesting. You'd get both gentrified and non-gentrified parts, and it's almost all pedestrian-oriented. That walk would be about 4 miles.

Others have suggested Clark, and that's a good suggestion, especially if you start all the way up in Howard since that will give you the biggest chunks of ungentrified parts of Clark. Walking from Howard all the way to where Clark hits Cermak is about 13 miles of walking. If you wanted to split it into a few smaller walks, you could walk from Howard to Wilson. Then Wilson to Division. Then Division to Cermak.

Another interesting mixed walk would be to walk Division from Lake Shore Drive to Homan (about 4 miles). The last mile or so can be sketchy, but it should be fine as long as you're reasonably street savvy.

Other interesting walks:

18th Street between Halsted and Western.
Cermak between Martin Luther King, Jr. Drive and Marshall Blvd.
Chicago Ave from Lake Shore Drive to California Ave.
Lincoln Ave either starting at Clark or Wellington and going possibly as far as Foster (or at least Lawrence).

[chicagomama]

What about walking down 18th street, passing the street murals and then heading to the Mexican Fine Arts Museum? You can stop in some panaderias or shops or restaurants on the way...

[RingWalk]

You know what was funny, I was riding around Canaryville the other day, and it really did not seem bad at all. (Halsted south of Pershing all the way to 47th.) For a long time I heard this place described as a "white ghetto" but it just looked like any blue-collar/middle class suburb to me. Actually some of the houses were very nice and most of them were well kept up, people were just out mowing their lawns, walking their dogs, etc. Obviously looks can be deceiving but it seemed fine to me.

On the way back I stopped and read all the signs at the old meat packing yard, and where the fire monument is, amazing history there.

I actually have walked through what I would describe as a 'white ghetto' before, South Boston in the mid-90s, and it was a whole different feel than this neighobrhood, to me.

[Alacran]

You will never walk through chicago north to south in one day.

[quigboto]

Milwaukee Ave takes you through some cool neighborhoods (Wicker Park and Logan Square) and there is lots of opportunity to check out the side streets around it, I don't know if there are any rough stretches on road southeast of Wicker Park, but I wouldn't be afraid to check any of it out in the daytime.

[jwaiter]

I vote for Madison Avenue from State Street to Austin Blvd.

[It'sAutomatic]

Milwaukee Avenue
18th Street
Chicago Avenue
DEFINITELY Dearborn or State between Division and North

As for neighborhoods, as in places to generally wander around:
-Old Town Triangle
-Wicker Park
-West Town/East Village
-Lakeview

[sydbarrett]

For the maximum level of seeing various cultures and people, I would go with the already mentioned Lawrence or (north) Western.

[ToriaT]

I love Lincoln Avenue. Also a vote for Clark Street. Other good streets might be Broadway and also Halsted.

[jdiddy]

Originally Posted by matzoman

I am looking for a street to walk on that goes through many ethnic neighborhoods, great deli,bakery,and variety of peoples to see. Gritty streets and neighborhoods with character I prefer. Nothing too polished or gentrified with lots of diversionary streets to wander down. What are your thoughts Native Chicagoans!

Lawrence Ave is the best fit for what you're looking for.