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Chicago's Windy City Hot Dogs


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#1 Rollin

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Posted 21 November 2009 - 08:03 PM

If your looking for a Chicago Dog or Italian beef on the west side check these guys out.
Nice family from Chicago just moved here and opened five weeks ago. All Vienna Beef.
So far I've tried the Chicago Fire Dog with the works $3.25. Spicy goodness with all the
proper fixins and poppy seed bun. Add fries for $1. Real good.
Also tried the Cheesy Beef sandwich with giardiniera $8.00 and fries for $1. When the guy
brought it out he said I hope your hungry. When I opened the wrap it was respectable.
It was dipped and I didn't think it hold up but it made it all the way and I was stuffed.
I know I shouldn't have eaten it all but it was delicious and you know a dipped sandwich
would just be a mess later. That's my excuse and I'm sticking to it.
Good size menu of sandwiches, dogs, hamburgers, and chili. Kids menu and beers on tap as well.
This place has been a few different food and coffee shops and never done well as it's a
little tricky getting in and out of the lot but from what I've tried I'll be back.
Chicago's Windy City Hot Dogs
8680 SW Canyon rd
Portland OR 97225
503-208-3031
No website yet.
On the corner across from the Lexus dealer.

#2 jennifer

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Posted 21 November 2009 - 08:59 PM

I just saw this place on Wednesday and raised an eyebrown at it. From the outside, it looks like it'd been there forever. I had no idea it was new! Thanks for the tip!

#3 BigDaddy

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Posted 25 November 2009 - 02:15 PM

I had to run out this way today, stopped in. Fairly extensive menu, and while it's not featured on the menu, they'll make a mother-in-law on request, so pretty authentic. Very good Italian Beef wet, ample portion of well seasoned beef and a good hot giardinera, standardly bad fries, and that was all I had room for. It's on the SW corner, ample parking by what looks to be a defunct strip joint.

#4 ExtraMSG

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Posted 19 February 2010 - 12:14 AM

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The Italian beef at this odd little SW Canyon Road outpost is tunnel-vision food: You start eating and you stop only to breath and wipe your brow. Thankfully the bun is robust enough to take a good soaking from the juices without falling apart while you work. It's a crude, down-and-dirty comestible, fit to give you the meat sweats. Yes, that's disgusting. It's also delicious. Deal with it.

Truth be told, there is nothing polite or mannered about the menu at Chicago's Windy City Hot Dogs. The most reasonable thing to choose from the big red-and-yellow board would be the authentic Chicago dog. It has everything you could possibly want or need. Vienna all-beef hot dog? Check. Poppy seed bun? Check. Pickle, sport pepper, tomato, onion, neon-green relish, celery salt? Checkity-check-check!

As is true with most Chicago dogs I've eaten (many in Chicago itself), Chicago's Windy City's has your daily allowance of yum. Still, it could be considered an appetizer given how small it is in comparison to other menu options—most of which, happily, can be drowned in cheese or chili at will.


The greatest service chemistry has rendered to alimentary science, is the discovery of osmazome, or rather the determination of what it was. ~Brillat-Savarin

Nick Zukin, Mi Mero Mole

Co-Author, Artisan Jewish Deli at Home

Formerly, Kenny & Zuke's


#5 BigDaddy

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Posted 19 February 2010 - 08:44 AM

The fries have gotten a lot better, still not go out of the way great, but crisper, better salt, a tasty version of the thin cut skin on. I can't seem to get away from the Italian combo, even if the beef is from the bag, it's tasty enough, but adding a grilled hot Italian sausage to it makes it heart breakingly good.

The chili tastes canned, which for my lowbrow burger stand tastes isn't always a bad thing, it goes well on the fries. One day soon I'll try the Maxwell Street lunch, fries topped with chili, cheese, chopped onion, and a chopped up Polish sausage. Look for that day as I'll either be in the obits or police record for fueling my car with noxious gases.

If you do get a chili dog, hold the green relish, it adds an odd sweetness and crunch that doesn't work. I'd recommend extra sport peppers.

Very friendly staff, they take time to explain all the options to people who don't quite know what's what and make some good recommendations.

Limited soft drink options, a fair amount of tap and bottled beers. Last time I stopped by, the happy hour special was $1 glass of Rolling Rock (like I should know it that's good or bad), daily special was a Polish with brown mustard, grilled onions and sport peppers, small fries and small fountain drink for $6.

#6 bbqboy

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Posted 19 February 2010 - 10:24 AM

If you do get a chili dog, hold the green relish, it adds an odd sweetness and crunch that doesn't work. I'd recommend extra sport peppers.

The very fact you would attempt to add relish to a chili dog makes me admire your mad scientist approach to junk food even more.

#7 vj

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Posted 19 February 2010 - 12:28 PM

The chili tastes canned, which for my lowbrow burger stand tastes isn't always a bad thing, it goes well on the fries.

It sounds like it's a Vienna Beef shop, so no doubt the chili is canned. But if you grew up with the Vienna Beef chili, that's what you have to have -- I love it, and really don't care for hot dogs with saucy non-VB chili unless they're Detroit-style Coneys.

Though if you're a chili fan, you might want to try the chilidog at K&Z's Sandwich works -- now that's some seriously good chili. Too bad they don't have a fryer.

(yes, I managed a Vienna Beef Chicago salad dog stand -- what of it?)

#8 BigDaddy

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Posted 19 February 2010 - 12:53 PM

VB posters all over the place here, so you win the sport pepper bracelet. I've had the K&Z chili dogs, which I love, it's dangerously close to what I make at home with beef, pork, and hominy. One nice touch on the combo, they almost always have a hot Italian sausage.

#9 Rollin

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Posted 19 February 2010 - 05:55 PM

My favorite lately has been the Italian sausage with grilled onions
and giardiniera. You'll need a nap after this Goliath. Damn tasty too.

#10 vj

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Posted 20 February 2010 - 05:20 PM

So, I came up with an excuse to go to West Slope, get lost in the neighborhood, and end up at Chicago's.

I really like this little shop -- lots of tables, a kind of a sports bar-ish feel, beers displayed in good sightlines. They have menu items that don't involve hot dogs or VB sandwiches -- like hamburgers, and corndogs. They also have video games -- dude!

I got a spicy dog with chili & cheese (aka the Dogfather), and chili cheese fries, along with a Rolling Rock. I was loving the fact that the place was almost entirely full up at 3pm on a Saturday. The counter girl was kind enough to give me a lime twist for my Rolling Rock.

I didn't time how long it took for the food to come out, but I did make it 15 pages into my book, so things seemed a little leisurely.

And here is the bad news, and I'm sure I'm the only one who's taking this so hard. Their cheese is nacho cheese - not cheddar or even shredded american.

While I was loving the atmosphere a whole lot more than Wayne's, the nacho cheese totally threw me off my game.

The fries are superior at Wayne's -- they dust them with a coarse salt which makes them like candy. Which is not to say the fries are bad at Chicago's, they're not. They're fine, in the steak plank category.

But nobody I know of here in town who does dogs has waffle fries, which are superior, particularly for cheese fries and chili fries...

So for me this was a mixed bag. I'm thrilled to have another Vienna Beef dog place in town, especially on my way home from work, but I'm really sad about the "cheese".

Hey Frank, I'd pay extra for real cheddar cheese! Please?

#11 ExtraMSG

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Posted 20 February 2010 - 05:47 PM

Just tell him that only someone from Philadelphia would use Cheese whiz. (Despite "you got my cheese whiz, boy" taking place in Chicago.)

The greatest service chemistry has rendered to alimentary science, is the discovery of osmazome, or rather the determination of what it was. ~Brillat-Savarin

Nick Zukin, Mi Mero Mole

Co-Author, Artisan Jewish Deli at Home

Formerly, Kenny & Zuke's


#12 polloelastico

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Posted 20 February 2010 - 09:46 PM

After taking my daughter swimming at the Southwest Community Center, this is her favorite place to go and get a hot dog and fries. BigDaddy is right, the fries have definitely improved...they were once too-fat steak-ish sized and somewhat limp but are more standard sized and crispy now.

I've had nothing but the Chicago dog with extra sport peppers each time I go, splitting an order of fries (only a $1 when you get a dog!) with my daughter, who gets a Jr. dog (which is the size of my Chicago Dog, just plain and not dragged through the garden).

One of these days I will have a burger or an Italian Beef.

The owners are great to my daughter, giving her a gummi hot dog or hamburger every time we finish our dogs. My daugher and I visted when the Saints were playing Cardinals in the playoffs, and I ordered a beer at the start of the second half. As I was finishing the owner came by with a pitcher of beer and offered to top off my nearly empty pint with more hefeweizen...for free. I had to refuse it as I was driving and with my daughter, but it was a pretty awesome gesture. In hindsight I should have just accepted and gave my daughter a couple dollars to play pinball while I watched the rest of the second half. And probably order another dog.

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#13 RM

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Posted 28 April 2010 - 09:01 PM

The last week or so I've seen the closed sign in their window on days when they used to be open. I haven't stopped by to see if there's a "vacation" sign or something on their door but it appears that this location may have killed another restaurant. Hope I'm wrong but if not, I'll miss both the chicago dog and the Italian Beef.

#14 vj

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Posted 29 April 2010 - 07:30 AM

Gosh, I hope you're wrong.

I was there, hmm, on the 14th and got dinner. They had a sign up saying they couldn't take credit cards, and when one of the car salesman ahead of me asked about, they said their machine was down. But maybe not.

I did get a spicy dog with shredded cheese rather than the nacho cheese, though I'm not sure if it was real cheese because it didn't melt.

#15 jennifer

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Posted 29 April 2010 - 11:08 AM

I just called them and got the phone company auto-voice that the call didn't go through. I'm guessing it's disconnected. Bummer, we were actually planning on trying this place tonight.

#16 vj

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Posted 30 April 2010 - 09:16 PM

I went by at 9pm this evening. No note on the door, everything inside looking just as it had and entirely spotless.

There was no sign that it had been open at all this evening.

The taqueria next door, however, was cooking outside. The place looks scary but the meat smelled goooood.

#17 Flynn

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Posted 30 April 2010 - 10:35 PM

Yeah, the one that's open 9pm-4am. It's catering to the nightclub next door. Someday I'll work up the stones to pull an Animal House and bust into that club. Come visit me at St Vincent afterwards.

#18 BigDaddy

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Posted 01 May 2010 - 07:22 AM

I've been meaning to hit up the taqueria; maybe we should get a group together for an early evening adventure. I'm well over 6' tall and large, so I don't think I'll be much of a target for any hooliganism that I don't initiate. But I'm not going in the strip club.

#19 Flynn

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Posted 01 May 2010 - 12:02 PM

I've been meaning to hit up the taqueria; maybe we should get a group together for an early evening adventure. I'm well over 6' tall and large, so I don't think I'll be much of a target for any hooliganism that I don't initiate. But I'm not going in the strip club.

Nah, I doubt the taqueria is dangerous. I used to live down the block from that nightclub (when it was Caribe). It wasn't a strip club, but it was waaay too 'stabby'. Lots of late nights with the Wash Co Sheriffs. I stayed the hell away.

#20 BigDaddy

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Posted 02 May 2010 - 10:39 AM

Not worried about the taqueria at all, it's the sherriffs who bother me. At least they don't get Beaverton PD. I wouldn't get my best friend out of that strip club, though, anyone fool enough to wander in there is homicidal, suicidal, or a divine madman.