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If you're leaving relatively early, I'm a big fan of going down Damen then taking Washington all the way out. It's the most direct route, it's got a bike lane almost all the way to Oak Park, and you pass through Garfield Park and a ton of really pretty houses and architecture in a part of the city most of us don't visit very often. It's a very interesting ride.
The downside is that you pass through some relatively high-crime neighborhoods, so the later it gets on Saturday the more dicey things become. As with a lot of neighborhoods, your comfortableness and safety depend on what time of day it is, how many people are with you, who you are, etc. But early Saturday morning it's a very pretty ride.
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