Welcome to The Windsor Tavern and Grill
The Windsor Tavern and Grill, located at 4530 N Milwaukee Ave, Chicago, is an inviting neighborhood bar that seamlessly blends a casual atmosphere with delicious food. Known for its hearty sandwiches like the Corn Beef Reuben and diverse salads, the establishment caters to a range of tastes. They serve inviting South of the Border fare, including nachos and tacos. The atmosphere is lively, making it an ideal spot for game days or social gatherings. Patrons rave about the friendly service and community vibe, making it a beloved destination for locals seeking great food in a welcoming environment.
- 4530 N Milwaukee Ave, Chicago, IL 60630, United States4530 N Milwaukee Ave, Chicago, IL 60630, United States Hotline: +1 773-736-3400
Welcome to The Windsor Tavern and Grill, a gem nestled in the heart of Chicago's bustling neighborhood on 4530 N Milwaukee Ave. This charming tavern is not just a place to grab a bite; it's an experience that embodies the spirit of community, camaraderie, and comfort food.
From the moment you step through the doors, you’re wrapped in a warm, inviting atmosphere, enhanced by friendly staff eager to make your visit memorable. The tavern's layout expertly accommodates both intimate gatherings and larger celebrations, with a cozy indoor area and an outdoor section perfect for enjoying those sunny Chicago days.
Now, let’s dive into the culinary delights that await you. The menu is a delightful blend of hearty sandwiches and enticing appetizers. For those craving something classic, the 1/2 lb Hamburger topped with fresh lettuce, tomato, and onion is a must-try at just US$9.50. If you’re in the mood for something with a twist, the Corn Beef Reuben on rye, also at US$9.50, transports you straight to deli heaven.
For a lighter option, the Windsor Wraps—available with either chicken caesar or spicy shrimp—combine crisp lettuce, onion, and cheese, all wrapped up with a side of flavorful rice for US$8.50. And let’s not overlook the array of mouth-watering appetizers. The Irish Nachos, with their hearty fries, melted cheese, and bacon, create the perfect shareable dish at US$9.00. For the cheese lovers, the Spinach Artichoke Dip, at US$7.00, is creamy and delicious, surpassing expectations.
Customer feedback underscores the tavern's reputation. Robert Taney praises the great pizza and friendly service, while Mark Garcia and Sergio Medina highlight a welcoming neighborhood vibe. It’s clear that the community is embracing The Windsor Tavern and Grill as their definitive spot, where enjoying a game goes hand-in-hand with savoring delightful dishes.
In addition, the tavern boasts a broad selection of beverages that complement the hearty grub. The absence of watered-down drinks enhances the overall dining experience, ensuring that every element—from food to drink—aligns with quality and satisfaction.
In conclusion, whether you’re in for a casual meal after work or celebrating a special occasion, The Windsor Tavern and Grill offers an inviting atmosphere and a menu that promises to please every palate. The combination of delicious food, a friendly environment, and exceptional service makes this spot a must-visit on your culinary journey through Chicago. So come on down, and let your taste buds embark on a satisfying adventure!

Great pizza. Friendly and wonderful servers on Friday evening

Great neighborhood tap. Good beer and prices. We only had chips and salsa but they were fresh and hot. Had a nibble of someone else's pizza before and it was pretty great. Next time I'll order it. Crowd seemed pretty friendly. They have a section in back for bigger crowds as well as an outdoor area. Good place to take in a game. Stop by! Edit - came back the next day for pizza and it did not disappoint. This may be my neighborhood go to.

New neighborhood spot! Finally got around to trying it after moving into the neighborhood last year. Great vibe, friendly staff, and will coming back to try the pizza!

I was here for a private party 5/3/25 and it was excellent.... service, atmosphere and food were Top Tier, no watered down drinks here. I normally get a pizza with toppings,was sharing a pizza with a friend who likes only cheese....and it was still tasty and Lott's-o-cheese and sauce. Owner and his staff made the whole event a success, Thank You!!

Great tavern style pizza and appetizers, everything you want in a great neighborhood bar.

Awesome service. Great neighborhood spot. Totally recommend stopping by for the vibes. Also Adams pretty cool too.

This is an awesome Chicago tavern and food. It reminds me of the many I've visited in my life but with better service and pizza then most. Great place and the people that work here make it better. Love it. Get the damn pizza. That's freaking awesome.

Best home towny bar you can find out this way. Good food, good beer, good people. Walk in be recognized, be safe, be happy.