1700N - LaSalle:
An elegant pedestrian bridge arches over Lake Shore Drive and North Avenue beach transitions now to an area capable of handling crowds. The air and water show centers here and there are gymnastics and other sports demos sometimes. The city recently rebuilt this historic ship shaped beach house. There's bathrooms, phones, snacks, even showers and blade rentals. Good freestyling space when not crowded.
See this photo and this photo. and this photo

1600N - North:
Multiple interesting paths through this tree covered area. Complex parking roads. On the other side of Lake Shore Drive are some of the city's most elegant parks and paths (though not easy blading).
See this photo.
Visit the Chicago Historical Society, 312/642-4600, 1601 N Clark.

1500N - Burton:
The path is almost peaking! Wrapping out from North Avenue, past a good fountain and the wonderful chess pavilion, an easy popular stretch begins. The upper path though flawless may be crowded, including elderly in rented pedal carts. Lower area is too rough.
See this photo and this photo.
Surf the City's Chess Pavilion web page.
Visit the International Museum of Surgical Science, 312/642-6502, 1524 N Lake Shore Drive.

1400N - Schiller:
We have arrived! All areas are soooo smooth, and the levels are jumpable. Careful, people have died here. The best bladers, jugglers, stunt bikers and bathing beauties congregate here on weekends when the weather is anywhere near decent. I try to make it every Sunday from about 1pm until dusk. Often someone has brought cones and great stunts can be seen. Always blade with the wind, say Hi to the lifeguards and be careful if surface is wet or you could go overboard. Skate Patrol sometimes gives free stopping lessons here.
See this photo and this photo and this photo.

1200N - Division:
Bladeable territory transitions to Oak Street Beach proper here with a dividing ramp, which I've used for some crazy jumps. Solid sunbathing here and for some reason a lot of bums. An underpass leads out to the awesome Michigan Avenue, take it with braking firmly applied.
See this photo and this photo.
Surf the City's Oak Street Beach page.

1000N - Oak:
I take this like a cool down lap. The path curves broadly around to almost a mile of perfect but amusingly slanted path.
See this photo and this photo.

800N - Chicago:
Now passing some of the most fabulous parts of downtown. Just a few blocks in leads to one of the greatest, hugest, glitziest chunks of top urban shopping and viewing on the friggin' planet, no kidding. Justifiably named "Magnificent Mile" this is a top tourist point. Though you'll get frowns, Michigan Avenue is notably bladeable here.
See this photo.
Surf the City's Water Tower pages.
Visit the famous John Hancock building, 312/751-3681, 875 N Michigan.
Visit the Museum of Contemporary Art, 312/280-2660, 220 E Chicago. Good blading in front.