If the size of the luggage for your Chicago IL travel is small, this leads to more convenience. You should make every little space that you have in your bag. If you have too many items to pack, do not carry a suit case. Instead, just use a traveling bag. Any crevice in the package ought to be packed with this item or the other. Weather conditions in Chicago are most likely very different from those in home town.
http://ezinearticles.com/?Nifty-Packing-Tips-For-Your-Next-Vacation&id=2405253
Make Use of A List
http://www.hubpages.com/hub/Vacation-Packing–List-and-Tips
In order to conceptualize the list of the items that you for your Chicago IL travel, you may have to figure out about what it requires a month in advance. This is the best time to start preparing a list of all the items that you will require. This is the best way of doing away with items that you really don't need. Making a list is one thing and following it is a different thing altogether. When packing, let the checklist guide you through the whole process. If you start adding in some items you think you had left out, then you will have made the first mistake.
Compress Items Such as Clothes Since You Will Need Them in Chicago
http://www.ehow.com/how_2335736_plan-walking-tour-through-chicago.html
You are going to be amazed at the amount clothing that can fit in a small bag through compressing.
Pack All Your Swimwear in the Same Place
http://www.ezinearticles.com/?Resort-Wear-Basics—5-Top-Tips—What-to-Pack
Do not put clothing is the same pack that contains toothpaste and shoe polish. This increases the chances of some items becoming damaged or misplaced.
Valuable Goods Need Special Packaging Styles for Safety's Sake
http://www.contiki.com/contikipedia/articles/suggested-packing-list-europe-summer
Put valuable goods in a bag that you know will always be near you throughout your holiday.