Windsor Tavern and Grill

04/09/2026

🍻 Open interviews for bartenders at our tavern on the northwest side.🍻

Interview times:
• Wednesday: 4–6 PM
• Friday: 4–5 PM
• Sunday: 12–3 PM

We’re currently hiring for 9–13 hours per week, with the possibility of adding more shifts. Bartending and food service experience are required, and experience with Toast POS is a plus. Bring your resume and 2 manager references.

Address: 4530 N. Milwaukee Blvd ask for Jon
Pay: $12.62ph + tips

04/01/2026

Join us on Monday, April 6th from 4pm-11pm for March Madness!

03/29/2026

03/22/2026

🍻 Jefferson Park Forward Pub Crawl! 🍻
Join us for an afternoon and evening of fun, friends, and community spirit!

We’ll hop between some of Jefferson Park’s best local pubs, enjoy great drinks, and make new connections with your neighbors and fellow JPF members. ~ Cheers!

03/05/2026

🎉 Happy Birthday, Chicago! 🎂
From all of us here at The Tavern, we’re raising a glass to the city we love — full of spirit, hustle, and heart. Here’s to another year of music, food, and unforgettable moments in the best city in the world. ❤️🖤

03/05/2026

🍀 Get ready to go green, Chicago! 🍀
We’re celebrating St. Patrick’s Day in true Irish style! 🇮🇪

We will be open on Tuesday, March 17th, from 4PM–11PM — plenty of time for pints, good vibes, and your best green outfit. 💚

Grab your crew, raise a glass, and let’s make this a night to remember. Sláinte! 🍻☘️

03/01/2026

March is for brunch lovers! 🌷

Join us every weekend in March for our Saturday & Sunday Brunch, featuring chef-crafted dishes, refreshing cocktails, and a relaxed atmosphere perfect for friends and family.

📅 Every Saturday & Sunday in March
⏰ 12:00 PM – 2:00 PM

Reserve your table today and make your weekends unforgettable! 🥂✨

02/08/2026

🏈 Super Bowl LX Watch Party at The Windsor!
Join us TODAY for Seahawks vs. Patriots at 5:30 PM CST! Game on all tvs with sound on, game-day specials, and halftime show with Bad Bunny.
Bring your crew to cheer on your team!

01/18/2026

Welcome to Bear Nation’s winter wonderland, LA ❄️ Bear down, Chicago – let’s freeze out the Rams! 🐻💙🧡

01/08/2026

🐻 BEAR DOWN at Windsor Tavern! Bears vs Packers NFC Wild Card LIVE Jan 10 (7pm kick)—beer garden fired up w/ fireplace, heaters & full game sound. Tag your crew—who’s roaring? 💙🧡

12/31/2025

Bar open late for NYE! The countdown starts now. Who’s joining the countdown with cocktails in hand? 🕛🍸

4530 N. Milwaukee Ave, Chicago

12/18/2025

🎄 Now on Tap: Begyle Christmas Ale! 🍺
Just in time for the holidays, this seasonal favorite from Begyle Brewing is a spiced ale featuring bay leaves, cinnamon, and a blend of European-style malts balanced by American ale yeast.

It’s smooth, warming, and best enjoyed with family, friends, and a little holiday cheer — a cozy reminder that it’s a wonderful life. ❤️

Stop in and grab a pint while it lasts!

12/17/2025

🍻 Tonight’s Tap Lineup 🍻
A curated selection of craft beers, a cider, and a sour, showcasing bold flavors, classic styles, and local favorites. From smooth stouts and refreshing lagers to hop-forward IPAs and bright fruit blends — there’s something for every taste.

Join us tonight between 4pm and 11pm grab some food and explore what’s on tap!

12/16/2025

Heads up, friends: we’re closed Christmas Eve and Christmas Day, but we’ll be ready with cold beer and comfort food starting December 26. 🎅🍔

Enjoy the holiday, stay safe, and we’ll see you for post-Christmas cheers! 🥂🎊

12/14/2025

❄️ Baby, it’s cold outside… but our Happy Hour is heating things up! 🔥

Join us for winter sips and cozy vibes — the perfect way to thaw out after a long week.

Happy Hour:
Wednesday-Friday 4pm-6pm
Saturday 12pm-4pm

Bundle up and bring your friends — good drinks, warm hearts, and winter cheer are waiting at The Windsor Tavern! ☃️