I go to Chicago for three things: fantastic food, rooftop drinks and beautiful architecture.
And when you go (or even if you're from Chicago), you have to go to The Girl and The Goat. It's a restaurant that boasts some of the most mouth watering food in the city. You can eat pig face, duck tongue, beef tongue, and every single part of a goat. Sounds adventurous (and it is!) but is SO delicious. Make a reservation WAY in advance though! It fills up quick. We had the fortune of walking by right when they had a cancelation, so we snuck in.
But long before this, and right after our plane landed, we were brunching across the street at TGATG's sister restaurant, Little Goat. French toast with fried chicken, a savory/sweet breakfast burrito and a cinnamon bun "the size of a baby's head" (as the waitress described it).
Definitely some great grub and worth checking out. I know it's a favorite of Walk in Wonderland's too. :P
That area of the city, West Loop, is like the Chelsea of Chicago. There's great little cafés and pubs, and plenty of cool murals to do photo shoots in front of. I had just flown in, so I was keeping it easy in a sweatshirt, trousers and high-tops. The pleated trousers elevate an otherwise super casual look. 'Athleisure' in my otter way.
Are you adventurous enough for beef and duck tongue?? How about an ear?