River West · Dive with good drinks

The Matchbox

A genuine Chicago oddity: one of the smallest, oldest bars in the city, still exactly as cramped and charming as its reputation suggests.

Nightcapsomething different
Neighbourhood
River West
Style
Dive with good drinks
Known for
Open since the 1940s · One of the narrowest bars in the city · Sold to new ownership in 2020 with the look and feel kept intact
Prices
$$ · cocktails ~$14–17
Getting in
Walk-ins only. Only
Food
Drinks only
Hours
Historically Mon-Fri 3pm-2am, Sat 3pm-3am, Sun 3pm-2am; confirm current hours
Address
770 N Milwaukee Ave, Chicago, IL 60642

WebsiteInstagramMap

Checked: Checked Nov 2026: official site lists current hours with no closure notice; Yelp reviews current through October 2026 and PUNCH's dive-bar feature corroborates ongoing operation. A stale Apple Maps listing showed 'closed' but conflicts with the live site and current Yelp activity, so it's treated as a stale map listing, not a real closure.

Photo: The Matchbox, from their website.