Make sure you’re taking the L, it’s the safest and least stressful way to get around. Google maps should route you through it pretty intuitively along with the signs. I’d recommend getting out of the loop. Wicker Park and Chinatown are fun places to walk around, eat, drink, etc. Rent a bike or just walk the lake front trail and hang out at the beach for a bit. I personally prefer Lou’s for deep dish. Enjoy the event, I’m curious to see how it plays out.