How To Get Downtown from Oak Park
There are a number of decent routes between Oak Park and Downtown. Each has its advantages and disadvantages. I live in the southeast quarter of Oak Park, so my most direct routes are Madison, Washington and Lake.
Most Direct: Madison St. Madison Street benefits from being recently repaved with bike lanes between Central Avenue and Pulaski. The remainder of Madison is relatively wide, and numerous traffic lights generally keep car traffic speeds low. Madison is also well lit at night and has a lot of pedestrians out all year long, as well as a heavy police presence at rush hours. The downside to Madison is heavy traffic during rush hours, CTA buses, which tend to bunch up and can be difficult to pass, and the stretch between Western and the United Center, which drivers tend to use as a speedway.
Almost as Direct When There’s No Snow: Washington St./Warren Blvd. Washington/Warren benefits from having a non-buffered bike lane running from Central Avenue to Des Plaines in the Loop. Washington is very narrow, however, between Austin and Central (and in Oak Park between Ridgeland and Austin). Washington is not a snow emergency street, and thus cars remain parked on Washington in heavy snow. As a consequence, its bike lanes become either snow-storage units or alternative parking spaces after heavy snows. I tend to avoid Washington in the winter.
Straight-but-Noisy: Lake Street. Lake now has buffered bike lanes extending between the City limits at Austin to Damen. Lake is also recently repaved between Austin and Garfield Blvd. The downsides of Lake are noise from the El, reduced sightlines from the El structure, and aggressive traffic (a lane of car traffic was removed for some of the bike lane, but many drivers willfully ignore the bike lane). Also, the bollards have been removed for the winter, making the bike lane a tempting passing lane for drivers. Lake is generally clear of snow west of Garfield, but areas east of Garfield are not clear.
South Loop Route: Harrison. Harrison offers the advantage of a pleasant jaunt through Columbus Park (between Austin and Central) and a number of narrow but relatively quiet blocks. The downsides of Harrison are long stretches of rough pavement, having to cross the Ike and make a left at Kostner, which can be very congested with truck traffic, passing through Rush Medical Center, which is always congested, and, when heading west-bound, having to ride the frontage along the Ike.
Far-South Route: 18th and 26th. By far my favorite route when the weather is nice and I have some extra time. I take Oak Park Ave. or Ridgeland Ave. south to 26th Street, and 26th in to the City. Take a left at California to 21st, and then take 21st across Western Avenue to Oakley, and Oakley to 18th. I then take 18th to Wabash and cut across the Loop at Harrison. Both 26th and 18th have bike lanes and traffic moves very slow.
Far North Route: Augusta. Although recently partially repaved, parts of Augusta are rough, but it’s generally a pleasant ride in the morning and early evening. The bike lane ends on the west at Kedzie even though Augusta is designated as part of the Grand Illinois Trail through Chicago and Oak Park. In Oak Park, Augusta has a bike lane between Ridgeland and Harlem. I take Augusta to Milwaukee.
North Side to Oak ParkGranted, Lawrence Avenue offers a marked bike lane that takes you as far west as you need to go...and Google Maps suggests either Diversey or Armitage. However, I have ridden Montrose dozens of times and find it to be a very bikeable street.
An ideal route from the North Side of Chicago to Oak Park is, in my opinion, west on Montrose, then South on Narragansett, then when you reach North Avenue, jog over to Ridgeland and continue South.
Regardless which street you take, after you pass Austin, start looking for Narragansett Avenue. Lawrence will dead end into it. If you're riding Montrose or Diversey, it's about seven blocks past Austin. If you're on Armitage, it will dump off into Grand which, unfortunately, runs at a Northwest angle so you wind up going a bit North before getting to Narragansett.