What are some interesting neighborhoods to walk through? (Chicago, Evanston: transplants, condos)

[eating while walking]

Hello,

I moved to Chicago about half a year ago and I've found that my favorite thing to do in the city is to go on long walks and seeing how architecture, street layout and demographics change from neighborhood to neighborhood. To give you some idea of distances, my favorite and most-repeated walk is to go straight east from Avondale (home), hit the lake shore and go south, turn west at Roosevelt until I hit UIC, then zig zag my way back to Avondale or just find Milwaukee Ave and follow that home. About 13 miles by my count. I love this walk but it's getting kind of old and I'm ready to see something new.

I have friends in Lincoln Park and Wicker Park so I feel like I know what those neighborhoods are about already. Don't need to walk there.

My biggest blind spots are the far north side and most of the south side. Would especially appreciate recommendations in these areas, but all recs are welcome.

Thanks

[jonnynonos]

I like hanging out/bumming around in Pilsen, particularly 18th street and Oakley/24th, which is the old "Heart of Chicago" Italian neighborhood; Taylor Street and the surrounding vicinity (sounds like you've already hit that); Chinatown; Bridgeport; Armour Square; McKinley Park (might stick to the daytime--can get kinda rough) via Archer... and I have done the walk down Clark Street from downtown all the way to Evanston and back several times. You don't hit anything too rough.

I also like taking Fullerton or Belmont west to the burbs, but since that's your hood, you are no doubt aware of those routes. Some cool old Polish neighborhoods and things over there.

[chicagobear]

Lincoln Avenue makes for a nice long walk with interesting things to see.

[ChiNaan]

Originally Posted by jonnynonos

I like hanging out/bumming around in Pilsen, particularly 18th street and Oakley/24th, which is the old "Heart of Chicago" Italian neighborhood; Taylor Street and the surrounding vicinity (sounds like you've already hit that); Chinatown; Bridgeport; Armour Square; McKinley Park (might stick to the daytime--can get kinda rough) via Archer...

These are all good suggestions. My only disagreement would be that I would say McKinley Park is similar in "roughness" to Pilsen, Chinatown, and Bridgeport. (That is to say not very, but certainly more so than Lincoln Park or Wicker Park.) I don't think it's quite as interesting as those, though. It's mostly residential, though the park itself is kinda nice.

Other than those and the ones the OP mentioned, I would add:
Logan Square / Palmer Square

Ukrainian Village / East Village / Division Street

West Loop / Greektown / University Village / Little Italy / Taylor Street (which could then run into Pilsen, Chinatown, and Bridgeport if you want a long walk)

And I think the U of C area and Hyde Park in general is super nice to walk around, though getting to and from it on foot involves some sketchiness from just about every angle.

I also really like the Lake Shore walk/bike path on the South Side. It's at least as nice as the North Side portion, and way less crowded.

[chet everett]

First I have to say that most people would consider a walk of more than a few blocks "extreme". Having said that I am also sorta fond of walking extreme distances and when I was younger would, with the right weather, "jog" from Hyde Park to the Loop on early morning strolls -- the openness and isolation of the thin strip of greenery and asphalt that makes for the "lake front bicycle path" means you are unlikely to encounter anyone other other folks to get some exercise... It is really scenic but there is NO real commercial activity and even "ice cream trucks" are rare. I would not recommend taking a more "inland" route to / from Hyde Park as even though most of the worst of the crime ridden CHA projects are gone there are still an awful lot of ways that something can go awry before good samaritans / law enforcement can come to your aid on rather desolate stretches of the southside...

Fact is the population density of north side areas from Rogers Park all the way to the Loop are a lot more in your favor --- something a simple as tripping on a busted sidewalk is gonna leave awful vulnerable for an extended period in many areas south of Chinatown in a way that is far less likely to happen north...

Funny thing too is that extending the 'density issue' by itself out to the corners of the city the SAME think happens -- if you care to stroll around Edison Park or Jeffferson Park there are just a lot more little mom & pop businesses in the typical block where someone is bound to pop-in an make it easy for a stumbling walker to go unnoticied compared to the sadly de-commercialized sections of West Lawn or Marquette Park...

Putting aside race and even the relative attractiveness of some neighborhoods I have to agree that at some level simple "are there people there" questions are probably a good guideline when deciding where to spend some time on an "extreme stroll".

[eating while walking]

Thanks for the quick replies guys. Just wanted to add that I am especially a fan of old-school industrial architecture like mills, storage silos, railyards and shipyards, so neighborhoods with those kinds of structures are especially good recs.

[ChiNaan]

Originally Posted by chet everett

First I have to say that most people would consider a walk of more than a few blocks "extreme".

Only if they live in the suburbs.

[ChiNaan]

Originally Posted by eating while walking

Thanks for the quick replies guys. Just wanted to add that I am especially a fan of old-school industrial architecture like mills, storage silos, railyards and shipyards, so neighborhoods with those kinds of structures are especially good recs.

In that case, you might like McKinley Park after all. You can walk along Pershing and see the old Stockyards and a bunch of huge old warehouses between Pershing and the tracks. They were starting to be turned into condos not long ago (not unlike the ones between University Village and Pilsen), though the 2008 bubble burst killed that quickly.

[jonnynonos]

There is a fair amount of drug dealing and gangbanging in McKinley Park and virtually zero yuppie/hipster transplants. Thus my distinction. Also last time I was there a native told us to stay away from the El stop because it was infested by crack dealers.

I don't pretend to have a great deal of knowledge about it but I certainly wouldn't compare it to Chinatown.

[TBideon]

The Loyola Campus is very pretty; you should go around there - some limited beach and water access there too