Estelle’s Wicker Park Reopening: Inside the Iconic Chicago Bar’s Moody Remodel and New Cocktail Menu

There are bars you visit, and then there are bars that quietly narrate your twenties. Since 1999, Estelle’s has been the latter. Perched at the electric crossroads of Milwaukee, Damen, and North Avenues in Wicker Park, the long-running late-night fixture has served as first-date confessional, last-call sanctuary, and neighborhood living room with better lighting.

Now, after months of renovations, Estelle’s returns with a Grand Reopening on Friday, December 5, and the transformation feels less like a reinvention and more like a well-earned second act.

A Redesign That Leans Into the Night

The remodel, led by Barker/Nester Architecture + Design and executed by Aberdeen Construction, trades brightness for atmosphere. Black leather banquettes line the walls. Warm tones hum under low light. Vintage-inspired wallpaper frames the room in quiet drama.

It is darker, sleeker, and more intentional.

But it still feels like Estelle’s.

The bar layout has been upgraded to support a newly imagined cocktail program, creating a flow that welcomes both early-evening happy hour regulars and the after-midnight faithful. The result is a space that nods to modern cocktail culture without abandoning its dive-adjacent credibility. No velvet rope energy. No pretense. Just better glassware and a deeper pour of ambition.

The Cocktails: Playful, Polished, and a Little Unhinged

The new drink list carries a wink.

Weekend at Bernie’s blends Buchanan’s Pineapple Scotch with Giffard Coconut and lime. The Spritzy Spritz layers Giffard Apricot, Bitter Truth Pimento Dram, lemon, sparkling wine, and soda. Gobblin’ Mode arrives bright and green with Ketel One Cucumber and Mint Botanical, Midori, lime, and simple syrup.

These are not museum cocktails. They are built for conversation. Built for round two. Built for a Friday that turns into Saturday without asking permission.

Late Night Still Lives Here

Estelle’s daily half-price happy hour now runs 4 p.m. to 7 p.m., reinforcing its status as one of Wicker Park’s most reliable after-work rituals.

When the clock slides toward 9 p.m., the tiny open kitchen behind the bar springs into action. Burgers, sandwiches, fries. Simple. Direct. Satisfying. The kind of food that steadies the room.

A new snack menu stretches from 4:30 p.m. to 3:30 a.m., featuring Black Bean and Cheese Firecrackers in crisp wrappers, French Bread Pizza, Bagel Bites, and a Cheese Board sourced from Beautiful Rind. It reads like nostalgia curated by someone who knows exactly what you want at 1:17 a.m.

Why Estelle’s Still Matters

In a neighborhood that has watched boutiques replace record shops and luxury rentals edge out walk-ups, Estelle’s remains stubbornly communal. Its longevity is not accidental. It is architectural, cultural, and emotional.

Some bars chase trends.

Estelle’s simply reopens its doors.

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