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What bike should I be looking at?

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T2urtle

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All my friends have these higher end $500ish bikes. I'm not that into it. But I wouldn't mind getting a bike I can ride to school. I live in the city and school is about 5 miles away. I never rode and owned a bike other then a bmx type of bike 13+ years ago.

Living in Chicago, theft is high so cheaper the better. I kinda think I should walk into Walmart and take something for $99. But all I hear about is this type of tire vs this for road and etc.

I'll be riding in the city. Streets and sidewalks. Sometimes in the rain but doubtful. Is there a certain type of bike I should be looking for?
 
Get yourself a city/commuter-style bike. Upright handlebar, "700C" size wheels, smooth tread. These bikes have wheels/tires that are the same diameter as racing-style bikes for better rolling resistance, but the tires are wider for more durability and cushion on city streets.

Shy away from MTB style bikes that are going to be heavier than you want (beefy frame, suspension fork, etc.) and have smaller diameter wheels and knobby tread tires.
 
My friends have been finding some lightly used high end bikes in the $300 range. I'm not sure I'm down with that because 1. Pricey is high in my eyes and 2. I might say screw biking (I have a car and motorcycle).

What should one of the more basic road bikes cost me.
 
Just go to Dicks or Walmart and buy the most reasonably priced bike you can find. If it is just taking you around town/school...the cheaper the better (less likely to get stolen or cost for maintenance.
 
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