Windy City Inn

Windy City Inn Chicago

Whether you’re a night owl or an afternoon tippler, Windy City Inn at the southeast corner of Irving Park and Oakley is the place for you.
Middle-aged locals and a late-night industry crowd all keep the place warm and friendly, and you might even be able to score some complimentary Ritz crackers topped with Cheese Whiz to accompany the cheapest beer in the ‘hood.

I first drove past Windy City Inn on my way to an audition, and I vowed to return because I found the place intriguing. I was immediately attracted to the French windows and old fashioned wooden bar sign hanging from the Irving Park façade. Once inside, the first thing I noticed (and still my favorite thing about the whole place) was the drop ceiling over hanging the bar with beautiful Christmas lights adorning it. Being in late January, I am assuming that those lights are a permanent fixture in the place as they certainly brighten up the place. Other things that brighten the dimly lit yet cozy bar are the three television sets in the front room, the biggest being set along the back wall, and all are usually tuned to the same station, though not everyone was even watching them to begin with.

Windy City Inn BarThe camaraderie at Windy City Inn is amazing. The bar is where most patrons hung out, lining most of the left wall of the front room. There are several other high top tables surrounding the bar as well, and a back room with a pool table and additional seating that is also rented out for private parties. Irish-American owner John Manning plans to add dart boards soon. That may be the only thing that keeps the bar from make a serious run as the best neighborhood hangout in North Center.

Upon my first visit, I stepped into the place, for starters, in the late, late hours of a Thursday night and found loud Metallica music bursting out of the digital jukebox. I looked around to see a crowd of people who, like myself, were no older than 30. They had all just come from their respective restaurant industry jobs and had already formed their drinking circles. I flocked to the only person I could find alone in the bar, a handsome jazz musician named Dan. He told me all he knew about the place, we shared a couple of drinks, and then I left.

Windy City Inn CrowdBeing that I knew the place is open from 11am until 2am, I felt a little curious of what the crowd would be like during the late afternoon hours of a weeknight, say Tuesday. So I returned to find a rather large crowd of gregarious pre-retirees. One of the friendly fifty somethings, Sam, told me that the place used to be a family owned German bakery and butchery, until about 19 years ago. Two years after that the owners of Windy City bought the place and reopened the doors. Sam, his wife and all of their friends were so nice that they offered me Ritz crackers with Cheese Whiz which they brought in themselves. Not that the food is bad at Windy City, by any means, it’s just limited.

Windy City Inn GangWindy City offers the finest of the frozen delicacies: fries, chicken tenders, chicken wings, mozzarella sticks, and nostalgically enough, tater tots. I also found their choice of pizzas to be interesting. Aside from the basic cheese, pepperoni, and supreme, they offer sausage and jalapeño pizza, as well as sausage with white garlic sauce. Not bad for a neighborhood North Central joint!

The bartenders do a whiskey and coke just as good as anyone, but what I really like is their selection of beers on draft. The choices include: Harp, Smithwicks, Guinness, Magners, and 312. These beers, in my opinion, should be the staples on tap at any bar. In addition to the draft beer selection, the secret to their success is that pints are served in 20-oz. glasses rather than the usual 16-oz. (or 14 like at Pepper Canister, Elephant & Castle and Pheasant & Firkin). All drafts sell for $3.50 except, strangely enough, for the locally brewed Goose Island 312 at $4.50. As far as bottled beer prices go, you can count on getting a domestic for $3 and an import for $4.

  • Windy City Inn Jazz Musician
  • Windy City Inn Pool Room

As far of the drink specials go, you can count on more being added in the near future, as bar management is currently changing hands. For right now, however, Mondays feature $2 bottles of Miller products and Wednesdays have $15 buckets of Rolling Rock (with five to a bucket). You can end your week with $2 Budweisers on Saturday.

“Hells yeah local goodness… Lovin’ me some cheap drinks with some locals who seem to live there. This bar is very welcoming and they try to throw down during holidays. They had a pretty sweet spread of free corned beef sandwiches during the St. Patty’s day party and they are always welcoming and serve up the cheapest of cheap drinkin’ ALL the time.”

Meghan P. on Yelp (March 15, 2009)

As far as this writer is concerned, Windy City Inn is a great place to go for a couple of drinks, whether you’re on your way home from work or stopping in to reunite with old buddies who you haven’t seen in 30 years. If you like Windy City Inn, you’ll also want to check out North Center’s other neighborhood mainstays, Gannon’s Pub, Globe Pub and Foley’s. For more information, check out the Windy City Inn Facebook page—Tater…