The only chicago ride we have firm plans but no date-very early on a saturday morning getting close into town and back north on lake shore drive. Other than that-we uns is wide open.

RIDE SAFE.
By very early I am hoping that you mean 5:00am. With the Taste of Chicago, the work on LSD, Wacker Drive and Congress Parkway the earlier the better. And if you are planning on running the drive (one of my favorite rides in Chicago) you need to start from the Museum Campus by the Adler .... great view of the city looking north. When you get to the north end you should take Sheridan Road north, the homes in Winnetka, Kenilworth and Highland Park are worth the ride. Most of the homes on the east side of the road are on the bluffs over looking Lake Michigan.
Sunday, you may want to head over to the Full Moon Cafe ... that's where a lot of bikes go for breakfast ... food is OK but you almost always see an interesting bike or two. The place is located on US41 in the town of North Chicago.
And if you feel really adventourus there is always Lake Geneva, WI.
And then for a little Ice Cream there is a really great place in Hebron on IL-47 at the 4 way stop just south of the WI/IL state line.
And if you are still around the following weekend (7/9 & 7/10) let me know and maybe we can get together and share some wind .... Starve Rock, Galena, Savana, Dixon and a whole bunch of corn fields!