Wicker Park & Logan Square

1. Sunday, Sept 27, 8:00 AM–2:00 PM — Sundays only, which is the whole point Wicker Park Farmers Market, 1425 N Damen Ave — Sundays 8 AM to 2 PM, May through October, in Wicker Park itself at 1425 N Damen — farm stalls, vendor pop-ups and live music. The day restriction is not a detail here, it is the plan: this market runs one day a week and September 27 sits comfortably inside its stated May-through-October season. Six hours is more runway than either of you needs, so arrive at 10 and you still have four.
2. Sunday, around 11:30 AM — roughly two blocks north on Damen, on foot North to the six-corners at Damen, North Ave and Milwaukee Ave — From 1425 N Damen to the six-corners where North Avenue, Damen and Milwaukee meet is roughly two blocks straight up Damen — no transit, no highway crossing, no decision. The car-free stretch begins at that intersection and runs along Milwaukee Avenue to Ashland Avenue. Naming the hop because we have to: this is the only movement in the plan, and it is a walk.
3. Sunday, Sept 27, 10:00 AM–6:00 PM — Meet Me on Milwaukee Meet Me on Milwaukee, Milwaukee Ave from North/Damen to Ashland Ave, Wicker Park — Eight hours with the cars removed: pedestrians and bikes get the roadway, restaurants put tables in it, shops run sidewalk sales and there is live music on the street. It is a pilot series — the last Sunday of the month across August, September and October 2026 — organized by Alderman La Spata's office with the Wicker Park Bucktown chamber and CDOT. Corroborated three ways: Block Club Chicago's July 14 announcement, the alderman's own event page linked above, and optionpremier.com's write-up of the three-Sunday series. September 27 is the last day of this edition's window, which is the polite way of saying this is the one plan here you cannot do this weekend.

Why it lands: A Sunday day-date with no ticket, no reservation and no closing time to race is the version that actually gets repeated. The market and the closure overlap from 10 AM to 2 PM, so there is a four-hour stretch where both halves are live at once — and if one of you wants to be home by noon, nobody has spent anything to find that out.

Weather backup: This is the September instance of a three-Sunday pilot; the next one is the last Sunday in October, per the same three sources. Same-weekend alternative in the same part of town: the Armitage County Fair at 2840 W Armitage Ave, Saturday the 26th and Sunday the 27th, $10 suggested donation, all ages.