Hi Mary Lee,
I would get the cookies into the freezer and freeze them until the week of
the wedding. You'll want to complete the decorating at least 24 hours
before they leave for Chicago to make sure the frosting is good and dry.
If you can decorate them in a day, then take the cookies out of the
freezer two days before you leave, let them thaw in their container, (that
way the condensation gets on the container and not the cookies, so they
won't get too soft) and decorate them that day. Let them dry 24 hours,
and package them up the night before they go. If you're too busy with
other preparations, moving this ahead a couple of days won't hurt. I
would say that once the cookies are decorated and in their packaging,
they'll be fine for up to a week.
If you are using Royal Icing, the recipe won't need to be altered. If
you're using the Meringue Powder Buttercream recipe on my site, I would
add an extra tablespoon of Meringue powder just to ensure that the
frosting dries well enough to not be damaged in transit.
You can package them in saran wrap or you can use small cellophane bags
and tie them with a ribbon, like this example:
http://www.karenscookies.net/shop/kc_images/ib_wedding_favor_01.jpg
I kind of like using cellophane bags because there is always a little bit
of air between the cookie and the bag, and it gives it a little extra
cushioning. You can get those cellophane bags at craft stores or even
Walmart, or if you can't find them locally, I sell them on my site.
For transporting, I would line a box with bubble wrap and then line the
cookies up in rows, on their edges (if you lay them flat in layers the
ones at the bottom tend to get broken). You could even add bubble wrap
between the cookies if you wanted to be extra careful. The last thing you
want is to get to Chicago with a bunch of broken cookies, so it might be
worth it to add a little extra cushioning. Top them off with a sheet of
bubble wrap, and you should be fine.
I hope that answers your questions. Let me know if you have any others.
I really need to add a "timetable" type of section to the tutorial pages.
I'll try to get that done.
Thanks Mary Lee! Good luck with your cookies and your wedding!
Karen