Of course there's a catch. First, you must want to go there. Visit the Oak Street Beach, a nearby restaurant or friend or just take a walk. I guess you might even try the Esquire Theater while it's still standing and if the timing is right.
A reasonable parking place in a prime location is on East Lake Shore Drive across from the Drake Hotel and going way east. The perfect time to go is on weekdays after 6:30PM. There is NO PARKING there from 4-6:30 PM but right at 6:30, there's lots of prime space and you can stay for 2 whole hours for $2.00 in quarters.
You might even want to take a chance on the Oak Street Beachstro, that place with the faux palms right on the beach itself. I don't really recommend the food or service but once a friend of ours hosted a terrrific party there by, I assume, buttering up the management with his considerable charm.
At the very least you can enjoy a glass of beer or wine while watching the passing scene. 312.915.4100.