I had a few days in Chicago this past week, and one afternoon my wife, and a good friend, and I decided to do a little day drinking. I dug into my list of must-visit spots and we ended up on the South Side at Stanley’s on Ashland Ave. & 43rd, right across from the old Chicago Stockyards. From the outside it’s just a plain nondescript brick building with almost no signage—you’d drive right past it if you didn’t know where you were going.
From the second we walked in, I knew we had found something special. Stanley’s has been around for 100 years, and stepping inside feels like stepping back in time: dark wood bar, vintage Old Style Beer signs, mid century furniture an old classic jukebox, and a spotlessly clean, no-frills vibe that feels like your grandma’s kitchen turned into a tavern. Shout out to Laura, was our bartender, who knew the area’s history and gave us some great food recommendations. She also pours a pretty stiff drink!
We didn’t eat this time (just missed the pork chop, au gratin potatoes and veggie special), but the menu is all hearty, homemade classics—burgers, patty melts, grilled chicken, steak sandwiches. With a view of the kitchen, I could picture my Grannie back there holding court and cooking. Drinks were strong, the service was friendly, and it felt like the kind of place generations of Southsider have been coming to for decades.
History is everywhere. This was once part of “Whiskey Row,” a strip that served stockyard workers, and you can still feel the generations of Southsiders who’ve come here over the last 100 years. Today, it remains cash-only, with a well-stocked bar, great cocktails, and a friendly bartender.
It’s not a dive bar, not a retro gimmick—just a real, old-school Chicago neighborhood tavern. Honestly, it was the perfect afternoon stop, and I’d go back in a heartbeat for lunch and...
Read moreYes, it's a bar, but they also serve decent food (at a reasonable price), which is why I go there. The menu changes, so call ahead. Some days, they have meatloaf, breaded pork chops, turkey dinner, roast pork, burgers, steak sandwiches, etc. Basically, American Diner food in a casual relaxed atmosphere. The specials come with mashed potatoes n gravy, a vegetable, and sometimes apple sauce. I wasn't crazy about the turkey, but the meatloaf is good with a baked ketchup top, a great homemade flavor (and it's a large portion). The breaded pork chops are my favorite, crispy on the outside and tender on the inside. I wish they served them on more days. The steak sandwich is great on some days, but sometimes the steak is kinda chewy. But for the price it's all great! Tip your server generously. She takes care of the bar and the tables, so be patient. The bathrooms are kept very clean and this place is CASH ONLY. Lunch is the best, they open at 11 am and there is a lot...
Read moreI rated this tavern a 5 because it is awesome. Wanda was the best. A Chicago Icon. It was so terribly sad of her passing 💔 but we all know someone has a new guardian angel 😇. I'm happy to see that Stanley's is going great with the love of the neighborhood and the family and friends of Stanley's. The food is delicious and the staff is awesome especially the one they call Darla the darling. She's as tough as nails but as sweet as she is nice. I love her dearly my very good friend of mine and my husband and we are very happy she is in our neighborhood 😊. Good...
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