Need to go to http://metro.teczno.com/ and download the osm.pbf file for Chicago. Then import it:

up:~ $ osm2pgsql -U postgres -c -G -d osm -S /usr/local/share/osm2pgsql/default.style ~/Downloads/chicago.osm.pbf

This will take a while. (Not really, 170s.)

Download a zip archive of the latest version of OSM Bright from https://github.com/mapbox/osm-bright/zipball/master and extract it.

Get these zip files.

http://tilemill-data.s3.amazonaws.com/osm/coastline-good.zip
http://tilemill-data.s3.amazonaws.com/osm/shoreline_300.zip
http://mapbox-geodata.s3.amazonaws.com/natural-earth-1.3.0/physical/10m-land.zip

Put them in the unzipped mapbox-bright directory, but don’t unzip them. In this same directory, copy the file configure.py.sample to configure.py. Then edit as necessary. The only thing I needed to do was to change the postgresql user to postgres and put a password for it in. Then, move the entire mapbox-bright directory to the Mapbox working directory, which for me was ~/Documents/MapBox/projects. Lastly, run ./make.py in the mapbox-bright directory. It creates an OSMBright directory, which will come up when you start TileMill. Then, edit away. It’s pretty cool!

Here’s my first map. I’ve been screwing around with the fonts, so they don’t look right. But still, it’s not bad.

OSMBright_0e1544 (PDF File)

OSMBright