Windsor Tavern and Grill

Windsor Tavern and Grill We have a large heated beer garden, with a TV, bags in the beer garden and a dart board inside the bar as well.
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From our hand-crafted specialty pizzas to our celebrated burger and cocktail combinations, the Windsor Tavern and Grill remains committed to providing a safe and fun environment for Jefferson Park and Chicago residents to eat, drink, gather and socialize! There also is a side patio with seating if you'd prefer getting some sun with a cold beer and a pizza !

09/29/2026

Join us at Windsor Tavern tonight at 7 for another fun busy night of trivia!
Round 1 - Picture Round: Game Shows
Round 2 - General Trivia
Round 3 - Audio Round: Songs By Actors & Musicians
Round 4 - Current Events
Round 5 - Who? What? Where? When? Trivia
Round 6 - Speed Round: Plays

09/28/2026

Windsor Tavern will be open tonight for the Bears game! Open at 4, Kickoff at 7:15. BEAR DOWN!

Join us this Tuesday September 22 for Platano, a Puerto Rican Pop Up based in Chicago. Fun cocktails, great food special...
09/19/2026

Join us this Tuesday September 22 for Platano, a Puerto Rican Pop Up based in Chicago. Fun cocktails, great food specials, and karaoke in our b**r garden!

7pm - 1am

Platano Drink Specials

Parcha sidecar $16
Cognac, Passion fruit, Lemon, Lemon Sugar, Pinch of Wepa

Smash Jibarito $16
Bacardi 8, Bourbon, Plantain oleo, Fat washed Angostura, Garlic tincture, Charred cherry tomato

Un Ma Mao $14
Cachaca, Aguardiente, Lime sugar, Super lime, Papaya

Lime in the coconut $14
Tequila, Coconut water cordial, Lime, Sazón Tajin

Can't wait to see you there!

Join us at Windsor Tavern tonight at 7 for trivia! Round 1 - Picture Round CerealRound 2 - General TriviaRound 3 - Audio...
09/15/2026

Join us at Windsor Tavern tonight at 7 for trivia!

Round 1 - Picture Round Cereal
Round 2 - General Trivia
Round 3 - Audio Round: Songs With A City In The Title
Round 4 - Current Events
Round 5 - Who? What? Where? When? Trivia
Round 6 - Speed Round: U.S. Cities

Hope to see you soon!

⚽ One tournament.🌎 The whole world watching.🍕 One place to be this weekend.Join us for every World Cup match Today & Sun...
07/18/2026

⚽ One tournament.
🌎 The whole world watching.
🍕 One place to be this weekend.

Join us for every World Cup match Today & Sunday!

07/14/2026

🚨Reminder!🚨

We're opening early TODAY & TOMORROW at 2:00 PM for the World Cup!⚽️

Call it a long lunch! ⚽️We open at 2:00 PM on Tuesday and Wednesday this week for the World Cup games!
07/11/2026

Call it a long lunch! ⚽️

We open at 2:00 PM on Tuesday and Wednesday this week for the World Cup games!

Tuesdays just got a whole lot better!
07/10/2026

Tuesdays just got a whole lot better!

Quick reminder that we are open tomorrow from 4:00-11:00PM for the World Cup!
07/05/2026

Quick reminder that we are open tomorrow from 4:00-11:00PM for the World Cup!

07/02/2026

⚽Plot Twist... We're Open on a Monday!⚽

We're normally closed on Monday, but we couldn't miss the action! Join us to catch the match on the big screens, enjoy your favorite drinks, and cheer with fellow fans.

📅 Monday, July 6
🕓 Open 4:00 PM–11:00 PM

07/02/2026

🇺🇸 Holiday Hours Update 🇺🇸

We'll be closed on Saturday, July 4th so our team can enjoy the holiday with family and friends.

We hope everyone has a safe and fun Independence Day!

Cheers to freedom—and cheers to seeing you after the holiday.

Happy Fourth of July!

06/18/2026

⚽️ World Cup action is here today and tomorrow!

Catch every match with us!
🍻Bar opens at 2 PM
🍕Kitchen opens at 4 PM

Grab your crew, enjoy cold drinks, great food, and watch all the World Cup excitement on our screens. See you here for the matches!

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

Join us on Monday, April 6th from 4pm-11pm for March Madness!
04/01/2026

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

Address

4530 N Milwaukee Avenue
Chicago, IL
60630

Opening Hours

Tuesday 4pm - 11pm
Wednesday 4pm - 11pm
Thursday 4pm - 11pm
Friday 4pm - 1am
Saturday 12pm - 1am
Sunday 12pm - 10pm

Telephone

(773) 736-3400

Website

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