Recent social media posts
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! ☃️
Address
4530 N Milwaukee Avenue
Chicago, IL
60630
To get to N Milwaukee Avenue in Chicago, you can take public transport by using the CTA Blue Line and getting off at the Logan Square station. From there, walk east on Milwaukee Ave for about 10-15 minutes until you reach your destination.
If driving, you can take I-90/I-94 and exit at North Avenue. Head west on North Ave for about a mile until you reach Milwaukee Ave. Turn left on Milwaukee Ave and continue south for about half a mile until you arrive at your destination.
Parking options include street parking and nearby parking garages such as Centrum Bucktown Parking Garage or Logan Theatre Parking Lot located within walking distance from N Milwaukee Avenue.
Opening Hours
| Wednesday |
4pm - 11pm |
| Thursday |
4pm - 11pm |
| Friday |
4pm - 1am |
| Saturday |
12pm - 1am |
| Sunday |
12pm - 10pm |
Alerts
Be the first to know and let us send you an email when Windsor Tavern and Grill posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.
What people say
Windsor Tavern Bar and Grill is a must-visit spot for anyone looking for a great time in Chicago. With its large heated beer garden, TV, bags, and dart board inside the bar, it's the perfect place to relax and unwind with friends. If you prefer soaking up some sun while enjoying a cold beer and delicious pizza, there's also a side patio with seating available.
The menu at Windsor Tavern Bar and Grill is nothing short of impressive. From hand-crafted specialty pizzas to their celebrated burgers and cocktail combinations, there's something for everyone here. And if you're looking for a fun event to attend, be sure to check out their annual Jefferson Park Forward (JPF) Social: Wearing of the Green Edition on St. Patrick's Day.
But that's not all - Windsor Tavern Bar and Grill also knows how to throw an amazing Super Bowl party! With free specialty pizzas all night long, $5 craft pints, $5 well mix drinks, and $4 Jameson shots, it's the perfect place to catch the big game.
Overall, Windsor Tavern Bar and Grill is a fantastic bar & grill that offers great food, drinks, atmosphere, and events. Whether you're looking for a casual night out or a fun celebration with friends and family, this spot is definitely worth checking out on N Milwaukee Avenue in Chicago.
