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.

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.

Coziest Cafe on the south side

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!