Possibly the smallest bar in Chicago, built into a triangular wedge of a building where Milwaukee Avenue meets the street grid at an angle. The room narrows to roughly three feet at its thinnest point, which means you are drinking in what is essentially a corridor with ambitions. The bartenders work in a space so tight they cannot pass each other, and the intimacy this creates — sitting at the bar with your elbows nearly touching the person beside you — is either claustrophobic or wonderful depending on your tolerance for proximity. The cocktails are surprisingly well-made given the spatial constraints, and the experience of drinking in a room shaped like a slice of pie is unlike anything else in the city.
Location
River West, Chicago
Map
Insider Intel
Martinis and Manhattans — classic stirred drinks that the bartenders can make in the limited space without needing a blender or elaborate garnish station. The cocktail menu is short and focused, built around what is physically possible in a bar this small. Beer and wine work well. Anything that requires muddling, shaking, or extensive preparation will test the spatial limits.
Weeknight from 7pm when you can actually get a seat (there are perhaps 15 in the entire bar). Weekend evenings fill the room to capacity in minutes, and the experience becomes standing-room-only in a space where standing room barely exists. The early weeknight window is when The Matchbox is most enjoyable — intimate, conversational, and spatially absurd.
The bar is genuinely tiny — do not arrive with a large group expecting to sit together. Two to three people is the maximum practical party size. The triangular building is on Milwaukee Avenue in River West, walkable from the Blue Line at Chicago station. Cash and card accepted. No food. The novelty of the space is the draw, but the drinks and the atmosphere justify a return visit. Capacity is roughly 25, and once it is full, you wait outside.