Can't help ya with the pool, but we have a map of the North Sheridan rd route on our web site (
http://chicagotriclub.com/...ions/sheridanrd4.asp). Hit the right arrow key under the page number to see the next section of the map.
It's around 50 miles round trip from Plaza Del Lago.
Pay close attention to page 7. Bikes are NOT allowed on this road. You can get a ticket if caught. Click on the "Click here to see a closeup of the detour" link for a bypass of this stretch of road.
When you get to page 12, you have a choice of riding on the bike path, or riding up old elm road. To see the old elm map, click on the Old Elm Road hyperlink.
There are plenty of gas stations, mini-marts on the way, so no worries about water/restrooms.