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.
This is my favorite music venue in the city. It's on a unassuming strange corner, has the perfect amount of dirty-ness, good beer, and great music. I've spent many nights here watching some of my favorite bands.
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!
Ongoing favorite place to sit at the bar or more covertly, at a table, chatting with a friend over the seasonal best. Continuous rotation of ingredients creatively meshed with tradition, their food is divine. Similarly, their personnel is familiar, friendly, fashionable and warm.