I guess this is the right place for this:
Visited Chicago this weekend and Chicago, in my *very much opinion*, shows a lot of urban planning done right which in-turn creates a great environment for a positive and enthusiastic tourist and resident experience near the downtown loop and near north side areas. I had only been in the winter once and this was a great time to go to see how well it's built. Aside from this, yes I'm aware it has plenty of problems such as a neglected south side, rapid-transit empty pockets, highways dividing other neighborhoods, not the best when it comes to neighborhood-serving stops (such as center of highway stops), lacking bike lanes, Lake Shore Drive, and other blight. But I'm sharing some of their impressive things I think other cities could learn from.
This is also understanding that Chicsgo is much larger overall land area, it shares the same county with some of its suburbs, and it was developed in a wider grid while still having a dense core. To me, it sprawls like western cities like LA, while still built tall with parks and transit like NYC too.
Anyway, something that I feel functions well in Chicago is the lack of building up to the lake compared to Boston, NYC, even Miami Beach etc. basically going to the water. I'm slightly comparing a port/harbor/river with a lake shore, but Chicago has a nice balance they strike with how they can build dense and tall set back from the park that sits on the lake shore. It seems to give a nice feeling to people as it can separate their recreation and outdoors from the dense and busy city blocks. This keeps noise and other pollution from parks, adds a level of clean and nature to parks, and doesn't mix areas too much. Yes, there's some sprinkled high rises right on the shore and Lake Shore Drive but Grant/Millennium/Lincoln Park along the Lake, puts the Esplanade (and others like the Hudson Path in NYC) to shame. It made me think that parks on the side function better than ones surrounded by roads and buildings? It also made me think that Boston could have reclaimed more natural shores even if it's just on the Boston Harbor - and that reclamation would in-turn create a healthier and positive relationship with the water. Again, this is comparing a lake to a harbor/bay, as well as a larger city Chicago to Boston, but still.
Additionally, I found that Chicago's skyscrapers create very odd shadows when downtown, but once you're out on the water far away enough, that's solved and gone. But it's a dense downtown area, so there will be dark spots between blocks - it just happens.
I don't think most of these things are really objective, but I wanted to share my opinions and observations about my fondness of Chicago. Lincoln Park is beautiful. And the decking in the loop was such a great idea.
Some more gripes about Chicago is that their trains shouldn't stop at all Park and Rides during off peak hours (blue line between ORD and downtown), its subway lines off-peak headways weren't too great if you wanted to go from far north (past Wrigley) to the loop (we just biked down along the lake for 6 miles instead). Also, if any city could use urban ring lines next, it's probably Chicago. Far too spider-y of a map. Not everything should have to go through the loop...lol.
