What items could I put in a gift basket that remind people of Chicago? (See details below)?

A gift certificate for Chicago Style Pizza. Or a recipe for it.

Great idea. Some thermal underwear in preparation for winter.

good idea about this basket . i really like it maybe you could put a tiny statue of the sears tower in it . maybe a pizzeria uno (chicago bar and grill) gift certificate

I'd also give them something from a local eatery, mabey a Goose Island beer hat. Mabey a portillos hot dogs bumper sticker? Not the "touristy" stuff either..like a stupid snow globe. You should give em some BBQ sauce too.

if they are moving TO chicago...wouldnt u want them to be reminded of where they left?

Some thermal underwear would actually be a good idea. They'll probably find it very handy when the cold unexpectedly hits them with a vengeance.... You might want to include a map of Chicago, a CTA system map, Fannie Mae chocolates, 312 beer (or any Goose Island-produced beer), Vienna beef hot dogs or Polish sausages.... We have beef stands in every neighborhood. A Chicago-style hot dog does not merely feature mustard and relish. The hot dog must be HEAPING with stuff. First of all, the relish should, ideally, be neon green. And yes, mustard and never ketchup. A good dash of garlic salt. Sliced tomatoes, diced onions. The bun must have poppyseeds -- never plain. Now, THAT is a hot dog and something you can call a proper meal!