Traveling with Celiac's Disease does not need to be a huge challenge. Gluten free is becoming more mainstream - which makes everything easier! All you need is a little research before you set out for the day. I usually travel with my laptop, iPad, and iPhone so I am able to research on-the-go but if you are a little lighter traveler than I am - you can certainly do all your prep work before you leave.
Google (obviously) and Urbanspoon are my two favorite places to research gluten free restaurants. Urbanspoon allows you to search by "gluten free" and a specific neighborhood in the city you're in - which is great. Siri (if you have iPhone) might be helpful also - but she hates me and usually refuses to point me in the right direction.
I knew I wanted to find a restaurant that served burgers (just randomly craving it) and was able to accommodate gluten free needs. Through Urbanspoon, I found the Sweetwater Tavern just a few blocks away from our hotel!
Sweetwater Tavern - 225 N Michigan Avenue. (right on the corner of this building)
Nothing but meat in these burgers!
They even had gluten free beer!
I ordered the Fiesta Burger - I can't resist jalapeños :)
Information / knowledge is always your best weapon for eating gluten free. Don't just assume any restaurant can accommodate gluten free - you need to check before hand. Be prepared to check websites or make a quick phone call.