Re: Buying a bicycle
Get a road bike. Don't be fooled into that mountain bike or hybrid bike crap. There are no mountains in Chicago and all the streets are paved.
For $500 you can get a decent new machine. You want to go to a shop that specializes in cycling. They can fit you properly. Additionally, the shop's mechanics build the bikes. Also the shops usually have some good used bikes. Do not go to a sporting goods store.
Be sure to get some kind of clipless pedal system. For example Look or Shimano. Spend some money on some good hard shoes you'll appreciate it.
Once the weather gets nice, riding on the lake sucks any where North of the Museums. But South of the Museums is great. You can go all the way to Indiana if you want.
Let me know if you have any specific questions. I'll be glad to answer them.
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