Chicago has great brutalist architecture but this is one I pass by all the time. It has been burned into my mind and I'm pretty sure it can fly.

DePaul Art Museum (DPAM) is a world-class museum located in the heart of Lincoln Park on DePaul University’s campus. DPAM is open to the public and presents four to nine temporary exhibitions per year with a permanent collection of more than 3,500 objects with strengths in international modern and contemporary art. DPAM enriches the university’s commitments to excellence, diversity and social concerns.  Built in 2011, the LEED-certified building was designed by Antunovich Associates.

Lost Eras has easily become one of my favorite shops to explore; hidden just outside of Chicago, it stretches far and narrow, crowded with lost treasures. Walking through it, it's hard not to begin imagining the stories of the objects that turn up in its walls, and the people that once held them. Not to mention the building itself is a piece of history, as in the 1920's it was home of the night club the "Club Detour" which had many artists play in it's halls such as Louis Armstrong, Count Basey and Ella Fitzgerald.

The 95th floor of the Hancock tower is a noisy, faux-classy tourist trap bar/restaurant, but the elevator ride (94 floors at 1800ft/min) and the view make it worth spending money on an expensive cocktail at the bar.

This is Ludwig Mies van der Rohe's first domestic structure in the United States, and it is a beautiful example of Minimalism. The house is located outside Chicago, but is worth the drive and the tour guides are pretty great. Due to flooding, the house and the property will undergo major preservation changes beginning in the next decade, so it's hard to tell how long the house will remain in it's current state.