What To Do In Chicago

You should pick your brother Jake up from jail in Joliet, go visit a nun from your childhood, talk to Cab Calloway, go to a church with lots of singing and dancing, drive over a bridge full of nazis, go eat at your friend's restaurant, buy instruments from Ray Charles, play a show with your band at a country music bar, get chased by the good ole boys, call up Maury Slein to book you and your brother a show far away from home, escape said show through a sewer pipe, get shot at by Jake's crazy almost-wife. At that point, you'll be 106 miles from Chicago, you'll have a full tank of gas, and a half a pack of cigarettes. It'll also be dark, but you'll be wearing sunglasses. You'll drive back to Chicago with Illinois state troopers and for a short time, the Good Ole Boys in hot pursuit.
Soon enough, the Good Ole Boys will drive into some water, and you'll be done with them. By the time you reach the Chicago city limits, you'll be chased by not only the Troopers, but the Chicago police, and the nazis from earlier. You'll end your journey at Chicago city hall, the Cook County assesor's office to be exact, still being chased by an army of law enforcement officials. You'll make it to the office just in the nick of time to deliver the money from your big show, and your childhood orphanage will be saved. When you come out, you'll be surrounded by SWAT team members wielding assault rifles. After you do that, you'll be in jail singing Jailhouse Rock. Have fun!