Although the size of Chicago feels like a different universe from Milwaukee, they are only about a 90 minute train ride away. I head to Chicago at least a few times a year, often for conferences. Since I'm usually in the same area for the conferences, the restaurants tend to be tightly packed in a small area, but there are TONS of great options in Chicago!
My big annual trade show is at the Merchandise Mart. There are surprisingly TONS of gluten free options within the Mart!
222 Merchandise Mart Plz, Chicago, Illinois 60654
An interesting concept for a cafe. They offer gluten free and low carb options. For the gluten free, they even have certified gf buns. The only non-gf item are tortilla wraps, which are low carb. The bread was really good, like so good I seriously questioned if it was gf. Personally, although I post about restaurants, we actually cook most of our food at home and I tend to eat few grains, so the bread felt really heavy to me. But it was delicious!
131 North Clinton (Between Washington and Randolph), Chicago, Illinois
The French Market is in a train station, I think I entered in the wrong door and then had trouble getting oriented and finding the entrance. But the link I shared shows a google map that is helpful. Anyway, there are something like 30 vendors, and quite a few had gluten free options. I saw/ate at the following:
131 N Clinton St #12, Chicago, IL 60661
They offer tons of gluten free options including bagel sandwiches, crepes, salads, pitas and breakfast bowls. A celiac friend of mine tried both the savory and sweet crepes and I had a sausage, egg and cheese bagel on a separate day. I went here two days in a row because the food was good and I had lots of options.
131 N Clinton St #7, Chicago, IL 60661
Raw and vegan food, with some of the options gluten free as well.
131 N Clinton St, Chicago, IL 60661
Pastry shop with a small location in the French Market. Offers some gluten free pastries as well as sandwiches with gluten free bread.