Matchbox Bar

Operating for over 75 years, The Matchbox holds a reputation as Chicago’s smallest bar, where the indoor bar has only a couple of seats before the room packs wall-to-wall. Pours range from ginger gimlets and shots of Jeppson's to signature margaritas with a powdered sugar rim. When indoor space fills up, patrons spill out onto the year-round patio, where dogs are welcome and guests frequently bring in outside food from nearby spots like Pie-Eyed Pizzeria.