Webster's Wine Bar

-Grubbing in Chicago  
European Wine Bar Vibes in Logan Square

I’m not the biggest wine guy which might be the reason I’d never visited Chicago's oldest wine bar until recently but at the same time I’ve been to as many restaurants in Chicago as anybody and Webster's Wine Bar is my neighbor so no excuses except I can't go everywhere, can I? It first opened in Lincoln Park across from Webster Place with which it shared a name and a street. They moved to Logan Square on it's 20th anniversary and it’s been a fixture in the neighborhood ever since then.

Locals Favorite in Logan Square 

Aside from its extensive selection of wine paired with some wonderful European vibes Webster's is also popular for its food. They have a knack for identifying the city’s best young chefs according to friend of da blog Kenny Zuckerberg (Kennetha222 on threads if you haven't already checked out over there). I didn’t know this until after we ate there but the people that help run Webster’s also run Rootstock and that makes a lot of sense. The kitchen is currently helmed by Chef Madalyn Durrant who was making great use of the summer bounty on our recent visit. We started out with the stuffed squash blossoms as those are always a favorite of ours. On our visit they came stuffed with sweet corn risotto, whipped chèvre, and a walnut romesco. As soon as I tried one I knew they weren’t bullshitting us when it comes to their seasonal menu claim. An order of Stracciatella (the cheese with origins in Puglia) was further proof. The rich and creamy cheese shared the plate with peaches, lima beans and more things I'm forgetting. The menu is so seasonal that some of it had switched within a week of our visit. An order of Cavatelli was served with sugar peas with asparagus with breadcrumbs on our visit but is now being made with a sungold tomato sauce, chanterelles, summer squash. 

Seasonally Inspired Plates at Webster's Wine Bar

She went with the striped bass for an entrée but I can’t remember exactly what was on the plate other than the fish but you can bet a very nice bottle of wine that it was seasonally inspired and fresh and very much enjoyed by my wife. I on the other hand decided to go with the one menu item that isn’t seasonal and that’s bc it’s always on the menu due to its popularity. I had heard good things about the Steak and Frites and I decided to get that since it had been a while since I had any type of steak outside of a tortilla. The steak part of the dish is an 8 oz grass fed and grain finished flatiron steak that’s cooked to a perfect medium rare. It comes pre sliced with a ramp chimichurri sitting on top and a cup of mustard cream on the side. The made in-house frites come underneath. I loved every component of this dish from the quality of the beef and the fries plus both of the sauces. Pricewise it’s a bit steeper than some other offerings around town but not by much so don't let that steer you away from one of the most satisfying plates of meat and potatoes in this real meat & potatoes type of town.

Steak and Frites 

Webster's Wine Bar
2601 N Milwaukee Ave
Chicago, IL 60647
(773) 292-9463
Website