If Chicago is a classroom, Andersonville is the student who’s sitting quietly while other students (i.e. neighborhoods) are cartwheeling around begging for attention. So it’s easy to overlook this area if you don’t live here. But that’s a mistake - Andersonville has some of our favorite restaurants in the whole city. Here’s our guide to where you should be eating.
It can be a red flag when a restaurant has an all-over-the-place menu full of dishes like empanadas with blueberry salsa, braised tofu, and a smashburger. After all, juggling is hard enough without it sounding like a Vegas buffet. But at Gadabout they do, and everything we’ve eaten here tastes pretty great. Since the space is decorated with furniture from the Brown Elephant, it feels like you’re having dinner in an apartment of a friend who likes old bookcases, fuzzy throw pillows, and vintage violin cases. Come here for some small plates and drinks, and to catch up with the people in your life who like resale shopping.
Middle East Bakery & Grocery & Cafe is (unsurprisingly) a counter service cafe attached to a grocery store, and it serves savory meat pies, falafel, shawarma, and sweets like baklava - with all the breads and pastries made in-house. Come here for a casual lunch or dinner, and then pick up some stuff to go at the bakery.
Head to Bar Roma for great rustic Italian food, and to feel like you just stepped into “Charming Italian Countryside Home” magazine. The space has a lot of wood and distressed furniture, plus bags of flour lying around to remind you that they make all their pastas in-house. There’s an entire menu section dedicated to meatballs, with varieties including spicy BBQ pork and braised beef cheeks. But we like coming here for their pastas - the cacio e pepe is fantastic, and you can’t go wrong ordering whatever pasta is the special for the day.
This is a popular neighborhood breakfast and lunch spot, and the breakfast is what you want to focus on when you’re here. They have everything from soprassata-wrapped baked eggs to cinnamon roll French toast to a corn cake benedict. The space looks a little like a farmhouse, and gets crowded quickly, so unless you get here really early, expect a wait.
It’s impossible to have a bad date night at Vincent. Literally impossible. If a date goes badly here, you need to reevaluate either yourself or the person you were with. Go for dinner, order a nice bottle of wine, and share some small plates (like the chicken liver mousse) and one of their five preparations of mussels (the house specialty).
Big Jones is a Southern restaurant serving a lot of old-timey dishes that we really like. You’ll need to get the perfectly-cooked fried chicken, and you should absolutely come for brunch, when they also make beignets.
Before Sushi Mike opened the new fancy digs in the West Loop, there was the original in Andersonville. This location has the same quality sushi, just in a more laid-back environment. So come here for sushi that’s good and reasonably priced. Tanoshii is perfect for a weekday dinner or low-key date night.
This bar has one of our favorite cheeseburgers in Chicago. It also has other food that’s a lot more interesting than what you’ll find at your typical neighborhood drinking spot. Order one of their light and fluffy bao (the pork is our favorite), or their green curry mussels. But whatever you do, make sure someone at your table gets a burger.
The term “gastropub” gets thrown around a lot, but for us, Hopleaf embodies its true meaning. This place has an exceptional beer selection and a food menu that goes above and beyond what you would eat in an average bar. The delicious cashew butter and fig jam sandwich takes a PB&J and makes it awesome, and you’ll wonder where it’s been all your life. Hopleaf is popular and doesn’t accept reservations, so count on it being crowded.
Taste of Lebanon is a casual, cash-only Lebanese restaurant. You can’t go wrong with the hummus, shawarma wraps, or their fattoush salad. It’s small, with only a couple of tables, so the best strategy is to order as much as you can carry and take it all to-go.
First Slice Pie Café
This is a welcoming little cafe serving all kinds of soups, salads, and sandwiches. And pie, of course, because with a name like First Slice Pie Cafe, there’d better be pie. It’s really the pie that you should be getting here (if that wasn’t obvious) - either the peanut butter or something more classic like the apple. Eat it there, or get it to-go. Or do both, and have more pie.
This sweet shop should be your go-to dessert stop in the neighborhood. Most things they sell aren’t made in-house, but the selection of Chocolate Shoppe ice cream (from Wisconsin), cake, and treats like chocolate-covered Oreos is still excellent. We particularly like the sundaes, which have generous amounts of chocolate fudge.