Small gifts to bring to Italy

Who are you bringing gifts to? Do you have an ongoing relationship with them?

I'm going for a wedding. I'm friends with the bride's side. I've never met the groom's family, so it doesn't have to be too personal or expensive as I'm not close. The groom is from Italy so I thought it would be nice to bring his parents something as they are helping people who are flying in for the wedding.

These days of international everything, it's difficult. Also you have to pack it.
A box of some luxury chocolate brand, like Ghiradelli?
It's really just a token to show you thought about it.
I'm British, so might have chosen a small boxed dish from Wedgwood or Royal Doulton.

You might look at some specialty sweets from your Windy City? :O)
https://windycitysweets.com

You might consider something small but local artisan made. Here's a good list of Chicago unique gift shops you might browse one near you. https://www.timeout.com/chicago/shopping/chicagos-best-gift-shops

Vanilla extract?! We don't produce that in the US, as far as I know. Maple syrup, maybe. Something local that you enjoy or something you made is a better choice. Even a handwritten thank-you card with a photo of the Chicago skyline.

I really don't know other than if they are on the young side (20's) often like baseball caps, and t shirts with popular US colleges like UCLA, Notre Dame, University of Michigan etc

Anything functional like maple syrup or vanilla will be a joke. Seriously -- people can buy ingredients like this anywhere in the world. I made similar errors in 1960. bringing gifts to people in Germany and was assured that the stupid things I was bringing would be very sought after after the war. Most of them stayed in my suitcase when I saw how embarrassing they were. I still sort of cringe at the advice I got back then.

Luxury and edible/ disposable is the key. Not Chocolate in summer. Bourbon, a good bottle of California wine or a local edible that won't melt. If you KNOW people are sports fans then hats etc make sense, but otherwise -- well what would the average American think if given a hat from a local soccer team? Picture books, maybe. A fair number of people like local pictures of places they haven't visited. Local scarf -- I have a really pretty one of the Chicago skyline someone bought me at the Chicago Historical Museum. Nice woven kitchen towels with local landmarks maybe? At least they can be used and used up. For young kids, Where's Waldo books can be a hit and don't require language.

The problem is that most things are available most places. Last year I bought my grandson a medieval toy helmet in Carcassonne which was a real pain to get back home -- I found the exact helmut on Amazon when I got back. Now I check before I buy stuff for the kids.

Another option is to plan to buy a really nice box of chocolates or bottle of Champagne when you are there. It is customary to bring flowers (and/or chocolates) as a hostess gift if invited to a home for a meal and you can acquire those there.

And even if tempted, not Malort.

I would forget the idea and treat your friends to a meal....

If flowers, not chrysanthemums or other flowers used for funerals or cemeteries.

All Italians like food, so something edible is always welcomed by us.
And Italians like what you consider very typical of your city/area. And something that you consider good and genuine.
Vanilla extract is a tradition of your city? Maybe you have a special producer of that natural flavor? If yes, could be a present. If is an industrial product made by chemicals (like the 95% of Vanilla extracts) should be considered very weird as present. But maybe you like to travel to Madagascar and you have at home some beans of Bourbon Vanilla: that is something special and appreciated!
Is maple syrup something traditional of your area? So, could be a nice present. And is true: we found maple syrup in Italian supermarket, so don't chose the same industrial brand. Maybe choose a bottle from a little handcraft producer who live in your area and made a special version: the storytelling is completely different and really appreciated by Italians.
The same could be for a spirit. Why not a bottle of whiskey? If your bring a Jack Daniel's is the same we found in every supermarket, but maybe there is the little local distillery who makes a tiny production that improve the present into something special.
Even chocolate could be nice as present. There isn't in Chicago a good pastry shop who make hand made candies? You never fail with them!

For Italians often is more important the message behind a present than the economical value. Do the effort to purchase something special. And yes: we have delicious chocolate and spirit even in Italy, but bringing something from Your city and from a local producer who spend a huge effort in produce something with his hands add a value that is much over the mere cost.

Ricky really hit the nail on the head. If you're going to bring alcohol that isn't a bottle of wine (which I agree you should buy there unless you have something very specific in mind that is American), tailor your selection to their taste. For example, if they like gin and tonics, find a small-batch gin distillery in Chicago and get a small bottle.

I think it's easier and neater to do as suggested and take everyone to dinner. Travelling with food can be iffy these days crossing borders.

Too bad you can’t take a Chicago stuffed pizza in your carry on!

Chicago? Small box of Frango mints all the way. And, yeah, I still miss Marshall Field's.

Sorry, Rachel. Frangos are from Seattle's Frederick and Nelson.

Hello,
I bring gifts for my host when renting their apartment, usually a keychain or a magnet or something that says my hometown....so anything that says Chicago would make a great gift! Ghiradelli chocolate is only made in the USA, but I am pretty sure I have seen it somewhere in Italy during my travels but would make a nice gift. Chi town tees or hats are also a great idea.