Open 6 days a week (closed on Saturdays), La Trailita (it's a food truck, but before their current truck, they were just a small trailer) serves some of the best tacos and quesadillas in Chicago, including tons of vegetarian options. They are open year round (even when it gets cold!). There is another taco truck across the street at the intersection, so make sure you're going to the right one (it's in front of a convenience store). I believe it's run by some ladies from the church it parks near. Recommend their tacos al pastor and potato quesadillas. Salsa is very tasty but very spicy!

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.

The Green Mill is Chicago's oldest Jazz club, open since 1907. Today it is an authentic link to past visitors like Al Capone and his henchman “Machine Gun” Jack McGurn who was the club’s former manager.

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.

Chicago is a gigantic open-air museum of hand painted signs and murals where you can still find gold leaf lettering in shop windows and ghost signs litter the city's brick walls. This handmade sign is on the wall of a Mexican garage near my apartment.