Eating out IS the hardest part. I can eat sushi if served just rice, fish, and lemon slices. I have to stay away from the reconstituted wasabi (maybe corn?) but the ginger is OK. There is a steamed fish dish at a local Thai restaurant I can eat. At Maria's Italian Kitchen (chain) they have a low carb, gluten free meno that works for me, generally chicken and veggies cooked in olive oil with garlic. But not sure if they are in Chicago or not.
There is a restaurant in Lake View that is ENTIRELY gluten free. It is called Senza and I ate there with some friends (gluten lovers) and we ll thoroughly enjoyed our meals. When I called to make a res I notified them if my intolerances. Our server kindly let me know what items I could order and avoid The List. It was great.
Any restaurant that uses brand sauces is out, like Cheesecake Factory. You want to find more chef cooked food.