This route from Chicago to Milwaukee is 99.94 miles, so with a few loops around a parking lot at the finish, you've got yourself a century. I'm not totally sold on an unsupported century, since I like the security of rest stops and a SAG wagon. But the idea of riding to Milwaukee is intriguing if we could get a group together... and if someone's friend/brother/mom can pick us up on the other side.

Here's the link.
View Interactive Map on MapMyRide.com

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Amtrack can take you back. Or there is a Metra stop in Kenosha, 15 miles from Milwaukee.
I've always liked the idea of this ride, though I've not yet had the chance to undertake it. Milwaukee's a city worth knocking about in; perhaps the ride could split after the laps around the parking lot with some riders hitting Metra or Amtrak and some rambling through town, camping or hitting a cheap lodging for the night, then riding back the next day or so. I feel like if it's worth the ride it's worth the going. Things are a bit crazy for me this year, so I likely won't be able to attend, but Chicago-Milwaukee seems like a good annual or semi-annual century ride for the chainlink.
This is something I've been wanting to do before winter this year. I'd stay the night and take Amtrak back. I've gone all the way up to Racine but never made it all the way to Milwaukee.

I've done two solo centuries (one of which was the Racine trip). Its no big deal. As Kevin Mulcky pointed out, the Metra covers you for 85% of the trip.
Also, there are some quality bike trails you can use rather than taking Sheridan all the way to Kenosha. Although I still don't have a good way to get through North Chicago and Waukegan.
Here is book that details choices of routes from Milwaukee-Chicago by someone who who has done the ride multiple times.

http://www.trailresources.com/b042.html

I am originally from Milwaukee and would love to join in a ride up there. I could probably offer a place to stay as well.
If you guys were up for it, I would totally do this. It could be the first chainlink century! Maybe we could pick a Saturday in early September?
I'd like to do this ride sometime. I've been meaning to do it for awhile and know some folks that already have.
This may be a pretty dumb question -- but how taxing are century rides? I'm pretty (very?) new to the biking scene (just bought my first real bike less than 2 months ago). A couple weeks ago I rode from the Loop to Libertyville ~45 miles and had no problem at all. Because I felt pretty good after, I felt I could make the trip back from Libertyville to the Loop the next day...this pretty much worked me. I made it back in about 3 hours and 15 minutes, but I was super tired.

Obviously I'm not about to try a century ride right now. I know I wouldn't be able to make it without significant breaks. But that was kind of my goal for the end of the summer / beginning of fall. In general (obviously it's different for everyone), do you think this is a reachable goal?
45 miles is v. good for someone so new to cycling. You're 1/2 way there already. The biggest obstacle to long distance riding is getting used ot being in the saddle for longs periods of time. So, just ride incrementally longer distances every weekend. 55 miles, then 65 miles, then 75 miles, etc. If you can do 80 miles without dying, you can try a century. So, yes its possible to work up to that by September.

I'm assuming that the chainlink century will be a somewhat relaxed pace (~15 mph)ride, though.
My firend Jon and I were talking about this last week - I think it's a great idea - I actually know a few people that would be down to do something like this -
That'd be great if we could get a group together. I'll just throw out some dates:

Saturday, August 9 (although that's next week so I'd probably want to give people an earlier heads up)
Saturday, August 23
Saturday, September 6

Any of those sound good?

von_ricke said:
My firend Jon and I were talking about this last week - I think it's a great idea - I actually know a few people that would be down to do something like this -
Leah - would totally be down for this! It might even turn out to be my first century. Dates given are no prob.

Cheers - Amy

Leah said:
That'd be great if we could get a group together. I'll just throw out some dates:

Saturday, August 9 (although that's next week so I'd probably want to give people an earlier heads up)
Saturday, August 23
Saturday, September 6

Any of those sound good?

von_ricke said:
My firend Jon and I were talking about this last week - I think it's a great idea - I actually know a few people that would be down to do something like this -

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