If I was to impart you with one word of advice, Double Potatoes from Homestead would be it.
The new Wicker Park spot is run by the same great dudes behind Roots Homemade Pizza, Fifty/50 and West Town Bakery & Diner. In fact, the restaurant is situated on Root's rooftop. With flora galore, strings of lights strung loosely above your head, mason jar candles and a bird's eye view of Chicago Ave, Homestead is set to be date night central. Rumor is that they're planning to bring in the occasional live entertainment, as well.
If scene isn't enough to satisfy you, the interesting and artisanal cocktails, most of which are spins on classic cocktails, and insanely fresh shared plates will get you into full on flirt mode. Come ready to expand your palate and take your time with each of these plates. There are so many flavors and you have all the time in the world to enjoy them. Homestead is one of those places where you want to experience your food. Not in a stuffy way, but in a very comfortable "let's step back and chillax" over hyper local deliciousness.
Enter through the Roots entrance at 1924 W. Chicago Ave., walk towards the back and your hostess will take you upstairs for either inside or outside seating.