We already have the "L" Challenge, where riders travel through every station on all eight rail lines.
How about adding a twist to that contest - get off the train at every stop and quaff a beer at a nearby tavern. That would probably take a bit longer than the current winning time of about nine-plus hours. But it would be more fun.
Now we have a CTA bar map to guide us on that trek. Check it out from Thrillist.com. Unfortunately, not every stop is mapped out. so you'll have to suggest watering holes at those missing stops. And of course you're free to suggest your favorites at stops that are mapped.