Where does one go to train hills out here (I'm on the north side)? I'm looking for something averaging 5-8% for at least a mile to do repeats on. Rollers would be nice, too. Thanks to any suggestions.

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For the types of hills you're looking for-New Glarus, Wisconsin. For hill training half an hour away-Lemont, Illinois.
I just finished a long ride out on the east coast that had a lot of those elevation change things called hills. I had been training mainly in Chicago and was worried about how I would perform on the hills. The ride went really well overall. I chalk it up to doing wind training: ride the lake front on really windy days. Ride hard into the wind whenever possible. Not the same as hills, for sure, but it will help.
Some days I swear the LFP is 300 miles long and uphill the entire way. Chicago winds are crazy.

Rob Foreman said:
I just finished a long ride out on the east coast that had a lot of those elevation change things called hills. I had been training mainly in Chicago and was worried about how I would perform on the hills. The ride went really well overall. I chalk it up to doing wind training: ride the lake front on really windy days. Ride hard into the wind whenever possible. Not the same as hills, for sure, but it will help.
I went though all my garmin reports and looked for the greatest elevation gains, this route had the highest numbers (without leaving the state) http://connect.garmin.com/activity/34983285

Joel said:
Some days I swear the LFP is 300 miles long and uphill the entire way. Chicago winds are crazy.
Rob Foreman said:
I just finished a long ride out on the east coast that had a lot of those elevation change things called hills. I had been training mainly in Chicago and was worried about how I would perform on the hills. The ride went really well overall. I chalk it up to doing wind training: ride the lake front on really windy days. Ride hard into the wind whenever possible. Not the same as hills, for sure, but it will help.
Rob Foreman said:
I just finished a long ride out on the east coast that had a lot of those elevation change things called hills. I had been training mainly in Chicago and was worried about how I would perform on the hills. The ride went really well overall. I chalk it up to doing wind training: ride the lake front on really windy days. Ride hard into the wind whenever possible. Not the same as hills, for sure, but it will help.

Christian Vande Velde also made the point that riding against the wind was almost the same as training on hills. Given that he was living and training in the suburbs (Lemont), I figure he knows what he's talking about.

I've shared this one before and will share it again. Climb bridges while riding a heavy bike (whether the bike itself is heavy, or has heavily loaded panniers). Doing this into the wind is a bonus. Do this frequently, then go to Wisconsin and ride a lighter bike on real hills. It's worked fine for me in multiple years.

S said:
Rob Foreman said:
I just finished a long ride out on the east coast that had a lot of those elevation change things called hills. I had been training mainly in Chicago and was worried about how I would perform on the hills. The ride went really well overall. I chalk it up to doing wind training: ride the lake front on really windy days. Ride hard into the wind whenever possible. Not the same as hills, for sure, but it will help.

Christian Vande Velde also made the point that riding against the wind was almost the same as training on hills. Given that he was living and training in the suburbs (Lemont), I figure he knows what he's talking about.

I actually think riding in wind is tougher--an invisible foe, & you're never sure quite when it's going to let up. But I just love hills. Oh well, will have to cross the border!
try Barrington Hills or Palos Heights
Go to Apple River Canyon state park. It's located in northwestern Illinois between Freeport and Galena. The only place in the state where I've had to use my "granny gear." : )

http://dnr.state.il.us/lands/landmgt/parks/r1/apple.htm
Now that area has some HILLS. :)

John Casey said:
Go to Apple River Canyon state park. It's located in northwestern Illinois between Freeport and Galena. The only place in the state where I've had to use my "granny gear." : )

http://dnr.state.il.us/lands/landmgt/parks/r1/apple.htm
I start in Barrington and ride to Hebron (near the border of Wisconsin). There is definitely more climbing than you'll get in the city, but it is a hike to get out there. I have taken Metra in the past. If you are willing to go farther, Madison's Iron Man course (which is sometimes marked or you can find it online) is a great 45 mile loop with challenging rollers.
If you want to hit hills in the city, there was a Tour da Chicago back in 1999 that took a route that hit a good portion of the "hills" here.

http://www.bikely.com/maps/bike-path/Tour-da-Chicago-1999-A-Few-Hills

Obviously you'd want to take out the hilly portions of that ride, and beware since things have really changed down on the "new east side" since 1999.

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