Favorite street intersections (Chicago, Addison, Lincoln: upper-class, hotel, parking)

[smegmatite]

Lasalle and Madison

Lincoln and Southport

[Master Jay]

Western/Lawrence/Lincoln; Good ol' LINCOLN SQUARE!- Master Jay from Milwaukee

[HumboldtBottle]

Originally Posted by rialtoma

And thank you all for the replying - so far seems like Milwaukee / Damen / North is where cool kids hang.

That's a big (and arguably inaccurate) generalization. It was hip central from the 90's to early (maybe even mid) 2000s but went through the gentrification that any place with that label eventually goes through. Now days I wouldn't call it the place where the cool kids hang so much as the place where aging yuppies who like to think of themselves as more hip or alternative than the Lincoln Park / Lakeview crowd hang. I acknowledge this even as someone who would be considered by many to be a member of that demographic. The "cool kids" are more in Logan Square (at least in the outer reaches), Humboldt Park, Pilsen, Bridgeport, and Hyde Park, among other bustling-with-creativity-but-still-affordable places.

OP, your question is a good one, but I have to admit I'm struggling with answering it. I think this is because I tend to think of my favorite areas in Chicago in terms of "strips" (or "corridors," as Chicagoans often say) rather than intersections. Off the top of my head there are stretches of several blocks that I love along Devon, Broadway, Southport, Milwaukee, State, Halsted, Western, Chicago, Taylor, and 18th, among many others, but narrowing them down to specific intersections gets much harder. I'm going to keep thinking about it, though, because it's an interesting mental exercise.

[Irishtom29]

It’s a conceit started by the baby boomers that one can be bourgeois and cool at the same time. That an accountant with an Audi is in some fundamental way different to an accountant with a Buick.

[edsg25]

State & Madison because it literally screams CHICAGO!!!!

and a happy 0 N/S and 0 E/W to all of you.

(not to mention it is home to a true Chicago icon department store, Carson Pir......er.......never mind.)

[Master Jay]

I'm also a fan of 24th and Oakley for the Northern Italian restaurants, Cermak and Wentworth for Chinatown, Taylor and Ashland for the "Little Italy" area, 26th STREET in Little Village (so much there!), and Northwest Highway and Oliphant (in Edison Park). For me, the diversity of all those places screams CHICAGO!!!! - Master Jay from Milwaukee

[ToriaT]

Lincoln and Wellington

Armitage and Sheffield

Taylor and Racine

[BigLake]

Originally Posted by Master Jay

Western/Lawrence/Lincoln; Good ol' LINCOLN SQUARE!- Master Jay from Milwaukee

I love Lincoln Sq., but that intersection is an ungodly, abysmal mess. Most unsightly, traffic-ridden, garbage-filled, bowling alley-less intersection in the city. I used to live three blocks away,


Let me throw out Wilson and Lincoln. That's a nice intersection with lots of good activity, interesting architecture nearby (Sullivan storefront, Sulzer Library), independent stores and still near Lincoln Sq.

[Irishtom29]

Originally Posted by ToriaT

Taylor and Racine

Stamping ground of the old Taylor St. Dukes. Taylor and May had a great bakery, DeLeos. I used to stop in and get a slice of sheet pizza.

[BigLake]

Originally Posted by edsg25

State & Madison because it literally screams CHICAGO!!!!

and a happy 0 N/S and 0 E/W to all of you.

(not to mention it is home to a true Chicago icon department store, Carson Pir......er.......never mind.)

So-called busiest pedestrian intersection in the world at one point.