I should go to 7-11, and buy a Big Gulp wit alot of ice and drink it in outside where it's very cold. People would call me crazy. lol I would probably do it too.
Nope. I think they can't accept tips even in grocery stores. When people help the customers carry their bags to their cars. They can't accept any tips whatsoever.
Does it apply to the children too? For the Taste of Chicago, alot of people sell drinks outside of the event for cheap. I'm not sure if they had permits or not.
Are you arriving at 5:30 am? If so, you have to factor in delays, getting your luggage. At the earliest, you'll leave the airport at 6 am.
Best bet is get someone you know to get in in line for you.