Fun dive bar in portage park. Nice neighborhood spot. Pizza is delicious and drinks were good. Parking available right out front.

Stopped it at Windsor Tavern and Grill in Jefferson Park and I was really impressed. It's a great neighborhood Bar with a relaxed atmosphere and one of the best tavern style pizza's in Chicago. The pizza was excellent, very flavorful, great tasting sauce, and the crust was perfectly made. We also had an order of wings, generous portion, with just the right amount of heat. For an appetizer we went with the artichoke dip served with homemade tortilla chips. You definitely want to try these. They have a solid selection of craft beers, the old-fashioned I ordered was nicely made, and I really enjoyed it. Great service by the friendly staff. Overall, a great experience. Can't wait to go back and enjoy more of the menu and definitely another tavern style Pizza! read more

I moved in to the area and decided to check this bar out for the first time last night, and overall the food was good and the atmosphere was great. However, my experience was ruined by the bartender, Sarah. She was rude, unwelcoming, and had a terrible attitude. I dreaded having to order drinks from her and ended up trying to get help from the other bartender instead, who was much friendlier and professional. It wasn't just me, Sarah was also rude to my friends, which made us so uncomfortable that we decided to leave and go to another bar. I'd consider coming back because the place itself was nice, but if Sarah is working, I'd probably turn right around and leave. read more

We came here on Wednesday for the pizza and wine bottle special which is $32 and an all day special. The sausage pizza is thin crust and very good especially with a glass of wine. We have been here a few times for the same deal and the place has a very chill atmosphere. The bartender was super friendly and very attentive. They have a decent selection of beers on tap. read more

Here is another local pub on Milwaukee Avenue. It has lots of great drinks along with somewhat basic food. The Windsor Tavern may sound like a fancy British place. For sure though it isn't. You can get a few local beers on tap along with greasy pizzas and whatever. Came in the last time and we kept it basic. It has a pretty good selection of beers on tap, and lots more in bottles and cans. There were a few we never had before this. It was about $7 for a draft. That's not that bad for a craft pint. A good one was the Surly Grapefruit Supreme, which was sour but also had a sweetness to it. We just got the Chips And Salsa. It's $6 for a basket. The pizza selection was meaty, and we caught a glimpse of one and it was pretty greasy looking. Great patio if wanting to sit outside of the bar. It often has drink specials going on. The pizza selection is pretty crummy but there's a few other things to eat thankfully. read more

The Windsor Tavern and Grill - Surly Grapefruit Supreme With Chips And Salsa - Bars Near Me - Chicago, Illinois

The pizza and wings were great! Our bartender was friendly and provided us with good service and authentic engagement throughout our visit. Space was clean and cozy inside with several TVs, jukebox, and darts. There was a nice beer garden upfront and another one inside at the back of the bar with a fireplace, tv, corn hole and some games. We look forward to coming back for the food and great atmosphere. Classic Chicago neighborhood bar! read more

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Got to this place before RobinTrower show at Copernicus theater show. Short walk. Yes it was packed but c'mon Unorganized. Poorly managed. Bar. Our table. Horrible service. Short staffed. Rude. Told to buzz off and deal with it. 1 hr to get a burger and salad. Pleaded for drinks. Get check. One star is generous. Never again. read more

I am so beyond extremely surprised with this one ! A classic old school neighborhood bar in the heart of Jefferson Park! Erica the bartender was helpful and friendly throughout our time there. Food was top notch! A standard burger and wings (Buffalo flavored) were all very tasty! The food is very good and everything including drinks was very decently priced. Perfect neighborhood bar along Windsor St! read more

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My husband and I came here for a mini night out. We got there around 7:45 PM on a Saturday night. The ambiance is nice and cozy, it wasn't too busy or rowdy at all. The service was good! Although, they did mix up my order and give me buffalo wings instead of barbecue. Luckily my husband ordered a wrap and appetizer, so we switched meals. Nice portions so expect leftovers! Wings 8.3/10 Irish nachos: 9/10 Wrap: 9/10 I would recommend coming here! read more

The Windsor Tavern and Grill - Buffalo wings, Windsor chicken wrap, Irish nachos - Bars Near Me - Chicago, Illinois

Fun and clean neighborhood bar with good food and great service. Really enjoy the vibe. Wings were a stand out. I will be back! read more

The Windsor Tavern and Grill - Sausage 14" Chicago's Finest Thin Crust Pizza - Bars Near Me - Chicago, Illinois

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One of the best kept pizza and beer garden secrets in Chicago! New ownership apparently since September and many great changes have already been made to staffing, cleanliness and the overall friendliness and feel of the environment. I spoke with the bar manager, Sarah, who was friendly and easy to talk with, and it sounds like there are a lot of exciting changes still coming, with bingo, trivia and live music being a few paired with continued hiring efforts which are underway. Having just moved to Jefferson Park, we look forward to frequenting The Windsor and watching this place grow! Love that we are in walking distance to such an awesome neighborhood bar. Wishing the new owner all the best and bringing back this classic Chicago pub and grill for the neighborhood and guests to enjoy. read more

Nice little, neighborhood, corner tavern. Modest menu but that should make for a quicker decision. Nice patio and parkway seating. read more

The Windsor Tavern and Grill - Decent selection of draft beer. - Bars Near Me - Chicago, Illinois

Neighborhood gem alert! Windsor has great bar food, really friendly staff, and a bonus indoor beer garden too. The food is simple, burgers, wings, nachos etc but solid. We came in and had some spinach artichoke dip (with fresh-made tortilla chips!) and a $30 pitcher of margarita drink special. Everything was great, we always have a fun time here. read more

The Windsor Tavern and Grill - Spinach artichoke dip with fresh house-made tortilla chips - Bars Near Me - Chicago, Illinois

Good pizza. Good selection of bear on tap. Friendly atmosphere. New owners since I've been there. I hope they continue the vibe.

Jon, the new owner is doing some cool things to make The Windsor Tavern better than ever. Same great tavern style pizza though. Relaxed, friendly neighborhood pub! I'll be back!! read more

Went in on a Friday with some friends. Never been here before but I've seen it's been in the neighborhood for years. We ordered the spinach and artichoke dip and a sausage thin crust pizza. The app was okay, dip was dry, but chips were fresh and crunchy. The pizza was not good. The server hyped it up saying the dough and sauce was made in house. As it might have been the crust was burned to a crisp, it was like we were eating chips and there was barely any sauce. The sausage had an odd taste to it, probably not fresh. The service was also very very slow. Won't be returning. read more

The Windsor Tavern and Grill - Sausage thin crust pizza 18in - Bars Near Me - Chicago, Illinois

The food was very good and prepared fresh. Waitresses were polite and the cook came out of the kitchen to make sure the food was satisfactory. I loved the older vintage bar lighted ambiance and the outdoor seating is a great option on a warm Chicago evening. Bathroom could use an update, but was clean. read more

So I have been to The Windsor Tavern a few times now, as some peeps I know really dig this unassuming watering hole at the corner of Milwaukee and Windsor just a few blocks south of Jefferson Park. They have outdoor seating along Windsor during the warmer months. The servers seem pleasant, but when it gets busy here you sometimes have to flag them down to pay up or check on your orders. The wait for the food to come out can take a few minutes so hang in there with your beverage and check out a sporting event on one of the TV's, or do some people watching amongst the locals who come here for a brewski. They do have a pretty good beer list here, along with a limited food menu. The sandwiches come out with fries that are crispy and taste like those at Popeye's chicken, so that is a good thing. The reuben with sauerkraut is a solid sandwich, and comes with sides of Thousand Island dressing and cole slaw. The burgers, grilled cheese sandwiches and pizzas are also popular choices. They also have something called Irish nachos on the menu, but we have never seen those come out yet. read more

First time, visiting from Wash, DC. Great food, friendly service, great little neighborhood bar.

The Windsor is a solid local tavern. Burger, Irish Nachos and pizza are all top notch. Decent rotating beer selection. Friendly and accommodating staff. read more

The Windsor Tavern and Grill - Solid Burger and Fries. - Bars Near Me - Chicago, Illinois

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Came in on a Friday evening with a group of ladies. We quickly got seated and ordered. The female bartender was nice, quick and responsive to our needs. The food was delicious, particularly the tortilla chips, and drinks were super cheap! Gotta love that, but.....the TouchTunes selection was very lacking when it came to hip hop and R&B artists. I get that they probably don't have a regular clientele that plays that sort of music but to have barely anything available in those genres kinda sends a message that they lack cultural inclusivity. It would have been nice to have more options to share in the experience of hearing songs we enjoyed too while dining. Idk, just a thought. Overall it's a good place for a drink and quick bite to eat. read more

I was in town 4 days and ate there 3 of them. The food and service were amazing. They were very accommodating and made sure we were well taken care of. read more

Our good "couple friends" really love the Windsor, and I've become a fan too. In permissible weather, sitting outside is nice, and their food and drink specials have impressed me as well. It's a nice local bar that does not get too loud, but it does get a bit crowded at times. read more

In from out of town. Great Bar-restaurant! They have outdoor seating and a beautiful indoor beer garden. The Chicken Caesar Wrap and their fries was delicious! I don't usually eat fries these days but they were worth eating! Pizza is great. It was a Friday night so there was a lively vibe. Definitely worth checking out for a night meeting friends where you can talk to each other. read more

Solid. As far as taverns go, this one's a beaut. Good food. Good service. Authentic tavern vibe.

The bar tenders here are completely rude specially if you don't frequently come here. I've came here many times and always rude this place is terrible. Don't come. Pizza is pretty good but customer service is terrible. read more

Both food and service were great! This is my third time coming here and I brought my sister for the first time since she wanted to walk around our neighborhood for dinner and she enjoyed it also!!! We are definitely coming back and bringing friends and family read more

Windsor Tavern is an interesting restaurant bar. Located on Milwaukee Avenue in what may be considered the north part of Portage Park, Windsor Tavern looks very much like an Irish pub from the outside. When walking in the outdoor theme in confirmed with all wood furnishings and bar. They have a couple TVs and the typical bar set up. They also have outdoor picnic table like seating. These tables have umbrellas. The menu is very interesting. Like I said above it has the feel of an Irish pub but the menu is much more representative of a mix of many local flavors. They have salads, steak and fish, burgers and sandwiches, soup, pizza, tacos, and all kinds of appetizers. The menu is not that large but they do have a little bit of everything. I had the dos tacos and they were pretty good. They had some drink specials written on a chalkboard that was placed outside. $5 Jager bombs if I recall correctly. I imagine they have all kinds of specials throughout the week. I look forward to coming by and trying a few other things out at Windsor Tavern. read more

The Windsor Tavern and Grill - Dos Tacos, chicken - Bars Near Me - Chicago, Illinois

This place has it all. Heated patio, sidewalk seating, good food, friendly staff, and good drinks. Only thing that could make it better was if the inside was larger. Sometimes there just isn't much room for us, so we make it a point to get there early if we want to be at the bar or an inside table. read more

We moved into the area this winter and come here often. Very friendly service and good selection of beers. The basket of fries is our favorite bar snack...very tasty. Usually order more than one basket! There is a dart board in the back. Good regular crowd and not too noisy. Definitely a neighborhood place. Looking forward to sitting outside when the warmer weather takes hold. Love that it's close enough that we can walk here too. We do a lot of our weekend stuff in nearby Wicker Park and Logan Square, but cant stay away from Windsor Tavern too long! read more

Italian Beef Crawl Stop #9: Windsor (6:57PM) We took the bus back after Mr. Beef & Pizza and the night was winding down, seven hours of beef later we had completed our pilgrimage through the northwest side. At Windsor, we had a few more drinks and there was one dartboard to play on. I was introduced to their massive garden patio in the back and people took out the bags and started throwing them. Most everyone was on beef overdose and there was much satisfaction from a fine afternoon of beefin' and beerin' it. The bar was great and the back patio proved to be the key to this bar since everyone else was inside watching college football. It was a great night and a great place to be with darts! Italian Beef Crawl 2010 was a great success, with the 2011 plan to feature the winners of years past. Windsor did the trick and I can't wait to go back! read more

The Windsor Tavern and Grill - Bars Near Me - Chicago, Illinois

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Good, cheap pub grub. Great beer garden. $2 domestics on Saturday night. The cheese steak is amazing. Try the cheddar sauce on your fries and attempt to not have a heart attack, I dare you. Friendly, neighborhood pub that is a tad less sketch than the package store up on Lawrence and a tad more comfortable than Hops and Barley (or Hops and Blackout, as we like to call it). Stop in. read more

A great local bar for cheap eats and great drinks! The visitors are mature and it doesn't seem like you'll run into too many children. I did visit on a Sunday where the Oscars were on during my visit. So maybe it was an off night. I could easily see this place getting crowded. I saw a lot of diversity among those that were seated and that fact alone will make me come back. I had a burger and fries with my 2 Sumpin' Sumpin's and a Jack and Coke. I was able to catch up with an old friend as well. The music wasn't too loud. When the tv turned on, that wasn't too loud either. The burger was juicy and the fries just the right kind of crispy. The bar tenders are incredibly friendly and attentive. There's no reason why I wouldn't come back. read more

I'm glad this bar is back open. It's a pleasant place. Old school pub that's a nice place to catch up with friends.

My wife and I heard about Windsor Pub since we moved back to the area and wanted to give it a try. We were expecting a relaxing atmosphere where we could have a calming dinner after a long week. The food came out fairly quickly, before our appetizer, and was very delicious. Our only complaint was our waitress who came by our table every 5 minutes to check on us. We felt like we were being rushed to eat and get out. We were halfway through our meal when she asked if we wanted boxes 'To-Go'. We stated that we were still eating. Five minutes later she came back and asked if we wanted dessert while we were still eating. We didn't see other waitresses hovering over their tables they were serving. read more

Nice vibe, but the server was a bit rude. Super unwelcoming and rushed us into ordering. One half of our tables order came out 10 minutes before the other half. No offer to refill water. Food was great but the people and service are off putting. Seems like if you're not a regular they don't care about your business. read more

The pizzas here are pretty lame. Wish they were better. They were flavorless store brand looking ones.

Hey hey, holy mackerel! I recently moved to the area, and was looking for: 1) A good neighborhood bar in walking distance (Who wants to pay for Uber or a DUI?) 2) A good place for snacks 3) A good Chinese place 4) A good place to get my hair cut And 5) A good pizza place Windsor Tavern takes care of 1,2, and 5. I'm racking my brains trying to figure out when the last time I had pizza and nachos that were that good. I bit into the pizza, and fireworks literally went off. I don't know how they make it, but that might very well have been the best darn pizza I've ever had in my 35 years on God's green earth! And this is Chicago, so that's saying something. The nachos were no slouch either. I had steak meat on mine, and not only was it seared to perfection, but the fat was nicely trimmed off as well. And THOSE might have very well been the best nachos I've ever had in my life! The beers are more than reasonably priced. Imagine my surprise when the tab comes after 3 beers, and I find out that I'm not even going to be ten dollars poorer! This after enjoying the company of the friendly staff and patrons. I think I found myself a winner here! read more

So I live in the neighborhood and based on what I've read I thought I should stop in and try this place. Dive bar....NO!! There are other dive bars in this area. Beer Garden, cork dart board, juke box, and good times here. Tried the cheeseburger and fries to see if the kitchen could handle "The Basics." It was somewhat under-cooked, but did have good flavor. They have a daily $2 pint special for domestic drafts. While you will find an occasional "local" who will talk your ear off, there is good atmosphere here. Friendly place, and I'll try it again. :) read more

I liked the place, although it's kinda small... it's got a lot of character!! Service is great and they have great specials daily. I really liked the pizza and would def go back in a heartbeat! Saturday Funday Destination..gdd read more