Any experience with a commute to Oak Brook from North Side
I bike to Oak Brook frequently from Oak Park (the Salt Creek Trail to the Prairie Path is a favorite 30-mile loop mostly on bike paths), so I have a recommendation from that perspective.
Depending on where you're at on the North Side, you could stay north and take Diversey west to Narragansett and then south on Narragansett/Ridgeland into Oak Park. Or you could find one of many routes south to Washington I would say (again, multiple options), and then take Washington west into Oak Park.
Once you are at Washington & Ridgeland in Oak Park, again you have a couple of options. You could take Washington west to the Prairie Path (I recommend picking-up the PP in Bellwood at Butterfield & Forest; the path through Maywood is choppy.) Once you bike west to Salt Creek, take the Salt Creek Trail south (it starts out as a residential throughway for a couple of blocks), pass under Roosevelt (careful, it floods often) and then viola, you're on the northeast end of Oak Brook!
Alternately from Washington & Ridgeland in Oak Park, you could head south on Ridgeland or better yet, East (similar flow, less traffic) to 26th Street and bike west on 26th Street to the Salt Creek Trail. The trail is always in fantastic shape and scenically winds its way west, under the Tri-State Tollway to deliver you to the greener residential pastures of the eastern side of Oak Brook.
If you really prefer to remain on the streets as opposed to trails, I'd say your best bet from 26th Street is to continue down Longcommon Road into Riverside, and then take Forest/Washington/Harding west, south on Brainard, west on 41st/Maple, across the Tri-State on a practical and magnificent pedestrian overpass, continue on Mineola to Oak Street and head north to deliver you to Graue Mill on the southeast end of Oak Brook.
Depending on the route you pilot and assuming you're biking from Wrigley Field (is that you Rizzo?!) to Oak Brook Center highrise, this reflects a 25- to 30-mile one-way commute. I always recommend looking at Google Maps with the biking feature on, just to give you a general overview of the bike-friendliness of a route, and then once you're there and bike it a few times, you'll find your favorite segments. Given one's comfort level, I think you'll find that it is sneaky-easy to bike from Chicago to Oak Brook, especially, and then beyond once you're there. Happy commuting!
I just wanted to endorse Brett's advice. I used to live in Berwyn and work in Oak Brook; I'd commute by bike twice per week.
During daylight, I preferred a hybrid of the suggestions above. On my way to work, I'd start on the streets (Forest-Washington-Harding) and catch the Salt Creek Trail at Brainard Ave. and Jackson Ave. in LaGrange Park, just a couple short blocks North of Harding. I don't know if that helps you, obviously, just thought I'd throw it out there. At night, I'd take the exact all-streets route Brett mentioned.