Scalping tickets is a violation of the law in Illinois, punishable by a fine when observed by the police. However, selling tickets near Wrigley Field is relatively easy if a few steps are taken. While the Chicago National League Baseball Club does not want tickets being sold for a profit by fans on its own property, the club resells its own tickets through premium ticket agencies. They have no problems with scalping their own tickets, but they don't want fans or other businesses doing it. A fan can also find himself in the position of having an extra ticket or two because other members in the group are sick, have to work and can't attend a game.
The main entrance to Wrigley Field is at the Northeast corner of Clark and Addison. It is not advisable to stand on that corner yelling "Tickets, I've got tickets." You don't need to be that close or vocal about it. If you have four extra tickets, you need to go two or three blocks to the south or the west and try to make contact with some of the Cub fans who may need tickets. As long as you are not too obvious or not on Wrigley Field property, it is unlikely anyone will bother you.
How do you know who needs tickets and who doesn't? People who want to buy tickets will be looking up and trying to make eye contact with anyone whom they think may be selling. It's a strange ritual that may include a wink, a nod or a smile. Then one of you begins a brief conversation. You may say, "Are you buying" or simplying "Buying?" With a nod of the head or a yes, you say you've got four seats and you are willing to sell them at $50 each or whatever your price is.
The buying party needs to respond quickly if you are going to get rid of the tickets. Allow them to make a counteroffer, but don't keep it going much longer than that. You are there to enjoy the game yourself and you don't want to waste the whole day negotiating on the sidewalk two or three blocks from Wrigley. The Cubs are an automatic sellout, so the law of supply and demand says you should get your price. Don't waste a lot of time bargaining.
If you are not finding many buyers in your spot, walk a bit closer to the ball park but never move on to Wrigley Field property until you are ready to walk into the game. As you walk toward the ballpark, quiety ask "Who needs two?" or "Who needs four?" You should get an immediate response.
Don't make the mistake of venturing onto Wrigley Field property, finding a willing buyer and then asking them to go back across the street with you. Undercover police walk around the ballpark property, however they rarely venture off the grounds unless they think they are going to complete a purchase started on Cubs' property. If you engage an undercover policeman, you will get arrested for scalping and will be forced to go to court and pay a fine if found guilty.