Restaurants with Gluten-Free Menus: This upscale Mexican eatery in the heart of Old Town offers plenty of gluten-free options such as grilled half chicken in tamarind-chipotle glaze and grilled flank steak as well as desserts including traditional vanilla flan with caramel sauce and strawberries. It also serves its famous guacamole made fresh table-side. Near Second City, it's a great place to meet for dinner or drinks if you're heading to a show. Locals love its monthly Tequila dinners which only happen once a month and feature a different theme. Reservations (which can be easily made online) for the monthly dinners are recommended since they sell out quickly.
Mexican: You haven't tasted guacamole until you've had it at Adobo Grill. Made tableside, it includes the freshest ingredients chopped right in front of you. It's smooth and tangy and hard to beat. Well-made margaritas abound to accompany the famous guacamole. This very popular restaurant is located in the Piper's Alley building and draws a young, upwardly mobile crowd.