I'm usually too busy to do this but when I can, getting out to the lakefront at night is truly one of the best things ever. There's something about the night sky, the water, wind and the city behind you that calms everything down.

The best new/used bookstore in Chicago––and with every sale, they put money towards buying books for classrooms in the neighborhood schools. Great selection, well organized, helpful staff, and they hold occasional events where they'll stay open late.

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!

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.