How to Spend Labor Day Weekend in Wicker Park (And Where to End Up)

How to Spend Labor Day Weekend in Wicker Park (And Where to End Up)

Labor Day weekend has a way of sneaking up on you. One minute it's a regular August Friday, the next you're staring down a three-day weekend — September 5th through 7th this year — with zero plans and a neighborhood full of options. If you're in or around Wicker Park, here's the good news: you don't need a plan. You just need a starting point. Ours is Ina Mae Tavern.

A Neighborhood Built for a Long Weekend

Wicker Park does long weekends well. The vintage shops along Milwaukee Avenue are made for slow, unhurried browsing — the kind you only really get to do when you're not squeezing it into a lunch break. The patios fill up early and stay full late. And with the days still warm but the light turning golden a little earlier each evening, it's the kind of weekend that rewards wandering: a coffee here, a record shop there, a long, lazy stop for food and a drink somewhere in between.

That's where we come in.

Labor Day at Ina Mae Tavern

We're leaning all the way into the holiday this year, with specials built for exactly this kind of weekend — the kind where you're not in a rush to be anywhere else.

$10 Hurricanes, Frozens & Whiskey Punch

Whatever your speed, we've got a $10 pour for it. Hurricanes for the classic New Orleans lean, frozen cocktails for when the September sun is still doing its August impression, and whiskey punch if you're settling in for the long haul. All weekend long, September 5–7.

$29 Wicker Park Favorites Platter

This one's built for sharing — chicken tenders, hush puppies, fried pickles, and fries, all on one platter, serving 2–3 people. It's the kind of order that turns "we'll just grab something quick" into an hour on the patio with a second round of drinks. Which, on a holiday weekend, is exactly the point.

The Plan (Or Lack Thereof)

Start your Saturday with a walk down Milwaukee Avenue — hit a couple of vintage shops, see what you find. Sunday, sleep in, take your time. Monday, treat it like the holiday it is. Whenever you land at Ina Mae, we'll have the platter ready to share and a $10 drink waiting, no matter which day you show up.

Ina Mae TavernLabor Day Weekend Specials — September 5–7, 2026Wicker Park, Chicago