52 Chicago Dogs — Jake’s Pup in the Ruff
Week 6: Jake’s Pup in the Ruf*. 4401 N. Sheridan
Many years ago, a local media outlet published a list of the ten oldest hot dog stands in Chicago. Jake’s Pup in the Ruff made the list, and I’ve had it on my radar ever since. This week I finally made the trip.
Jake’s is in Uptown, which is probably one of the sketchier neighborhoods on the North Side. And I emphasize North Side. By Chicago standards overall, it’s perfectly manageable. It’s not comparable to some of the neighborhoods on the West Side. Still, it’s a somewhat different experience than the other hot dog stands I’ve visited so far.
I’m talking about the clientele. There were a couple of people who looked to be one step away from homelessness, quite a few more people of color than I’ve encountered at the other places, and a real mix of people and backgrounds. It’s Chicago. And honestly, I think it’s pretty cool seeing everybody enjoying the same thing. We’re all just looking for a good hot dog.
And a good hot dog, I got.
These were some of the best I’ve had so far. Nice soft buns, hot dogs with a good bite, and, for some reason, sport peppers that seemed hotter than usual. The fries weren’t my preferred style, but they were piping hot and crispy. And they gave me a TON of them. No complaints about portion size!
I decided to get a little exercise to help work off the hot dogs and fries, so I walked there and back. About four miles round trip. It was a beautiful day, the walk was enjoyable, and the food was terrific.
Sometimes everything just comes together. A new neighborhood, a little exercise, and some excellent Chicago dogs.
Six down. 46 Chicago dogs to go.




