Windy City Hot Dogs

Well this place didn’t last long. I drove by and the signs are down and trucks parked outside. They didn’t even make it to summer. UPDATE: I heard from the local gas station attendant that an illness forced the owners to close it. Sad.

NOTE: This review has been updated to delete the name of the competitor since it was apparently deleted as being too much of an ad for that place. You’ll have to look it up yourself; it starts with «Way – ».
To the best of my knowledge, there are two places in Portland claiming to serve authentic Chicago-​style hot dogs: this place and W — -.
Both are «authentic», but W— is VASTLY superior to this place in almost every way.
The high point of this place is the Chicago dog. It’s pretty good, but just a tiny bit less fresh, and less tasty, than [you know]. It’s as if, after you ordered here, they drove over to W — - and drove back with a Chicago dog and let it sit under a heat lamp for 40 minutes before serving it to you. It’s the only reason I’m not giving this place one star.
I also ordered the cheese fries. The fries, I’m certain, are the kind you might buy in a 50 lb. sack from Costco — completely average. The «cheese» is the same stuff you get on your nachos in a movie theater. W. has them beat hands-​down — with better fries and cheese that’s actually quite good.
The atmosphere and décor here is similar to a generic, small-​city airport bar. It’s a «blank-​slate» restaurant with generic furniture and thirty pieces of «Chicago memorablilia» on the walls. Wa — s may not win any awards for décor but it’s light and airy and fun to be in. Not so here.
(I should add here that I don’t work for W — -, but I have spent 25 years seeking out and sampling Chicago dogs and have a fair amount of experience with these types of places.)
Finally, I have to say that the employees here seemed bored and indifferent; whereas at, yes — [COMPETITOR], the folks behind the counter really seem: 1) like they take pride in their food and 2) like they are really from Chicago.
Again, the Chicago dogs at this place are fine, and in a pinch, they’ll do. But if you’re in search of the best Chicago dog in PDX, you should be visiting… (I won’t even say it.)

Good to find a real Chicago Style hot dog in Portland. Found it last week and heading back again for lunch today!!!

There’s a new Chicago hot dog in town, and it’s a real «wiener!» (Oh, I know, «groan.»). Chicago hot dogs aren’t all that easy to come by in Portland, and Chicago Italian Beef & Sausage combo sandwiches are even rarer. Yes, there is that place across the river run by that cantankerous old coot, but the differences are elementary. Windy City buys all their product from Vienna Beef, the preeminent Chicago vendor, and the «other guy» makes his own.
One could argue the advantage of either method, but if you’ve been to Chicago, or lived there twice, like I have, you get a craving for the «real thing», and Windy City fills the bill, seemingly ordering all of their provisions (and decorations) from Vienna.
Windy City’s menu (below) covers the full range of Chicago style foods, from the loaded up Vienna hot dog (mustard, relish, chopped onion, tomato, pickle, sport peppers, celery salt on a poppy seed bun), to Italian Beef (with giardiniera or sweet peppers), the Maxwell Street Polish, and sides like cheese fries or chili cheese fries.
Windy City also has burgers on the menu, I’ll have to get back there to sample those, and I’m interested in chowing down on the «Rush Street Lunch», chili cheese fries topped with a chopped polish and bacon.
Kid’s menu, a couple of beers, and meatball and pastrami sandwiches to boot!
Both the dog and the combo were spot on, exactly as one would experience in Chicago. For my money, (and that’s all that counts with me), Windy City’s Italian Beef is better than the other guys, because it is the familiar Vienna texture and seasoning.
Windy City is at 8680 SW Canyon Rd., call 208‑3031 if you’re inclined to place your order ahead of time, or for carry out. Open 11 – 7 six days.

Huge dogs, great fries, and authentic Chicago personality behind the counter make this place a winner in my book. I’d never heard of it until a coworker brought a group of us over– I’ll definitely be dragging others back to my new favorite dog joint. The regular prices are pretty reasonable, and the lunch special prices are unbelievable for the amount of food you get. Get in early at lunch if you want to eat in– the seating fills up quickly, and the parking lot’s pretty small.

So far so good, Windy City. It’s been awhile since I’ve had a proper hot dog with pickles sliced long ways, chunks of tomato, and a poppyseed bun.
All this was missing was a luke warm Old Style and some bikini-​clad honeys shaggin’ fly balls in the bleachers.

Finally a decent Italian Beef sandwich on the west side.
Just had a great Italian Beef sandwich at this new restaurant. My SO had the Dogfather Chili Dog, a spicy dog with chili sauce, tasty if you like spicy dogs. If you like spicy gaiardinera on your Italian Beef they have the best I’ve found in PDX so ask for extra as they are a little stingy with the relish. Windy City serves Vienna Beef hot dogs.
Decent selection of beers but definitely not beervana. Skip the fries and get one of the bread sides. The fries are adequate but nothing to write home about.
Most of the menu items are less than $ 5 for hot dogs and $ 8 for sandwiches.