Hi! I am going to try to bike from the Midway area (Harlem and the Stevenson/55-basically) up to Avondale (Belmont/ California) tomorrow. Does anyone have good tips for routes? I usually don't ride southwest so I am not familiar with that area's bike routes.
A very simple route would be Archer to Kedzie, Kedzie North to Belmont, Belmont to California. Depending on the time of day, Archer isn't terrible, riding condition-wise. You could also take Harlem up to Ogden and then Ogden to Austin, Austin to Diversey and Diversey to California.
If you want to add an extra mile or two there is a forest preserve north of 55, west of Harlem which will get you into Riverside from which you can take Riverside Drive through to Berwyn and then take side streets or Oak Park Ave or Ridgeland through Berwyn and Oak Park, use Narragansett to connect to Wrightwood and then take that east through to Logan Square, I believe you can take Wrightwood all the way to the Logan Square monument, though it might jog in a few places.
That area doesn't have bike routes like Chicago does. There are some trails thru the forest preserves, but that's no help if you actually want to bike somewhere.
The side streets are good, though.
The best route entails taking Harlem north to 46th Street (which is the worst part of the route; If it bothers you, take Pace bus #307 north), then 46th to Oak Park Avenue, Oak Park Ave north to 38th or 37th, go east 1/4 mile to East Ave, East Ave north to Lake St in Oak Park, then go north through the paved area next to the high school and re-join East Ave, take East north to Augusta, Augusta east to California, California north to Belmont. I don't know if they ever fixed the pavement between Kostner and Central Park on Augusta, so that might still be bumpy. But this is the route with the least traffic, and is more low stress than riding on car-choked arterials like Ogden or speed bump-filled Wrightwood.