Windy City Eats

It was a wet and dreary November morning when Mrs. Hotdogman and I trekked down to the South Shore to run an errand. We don’t get down that way too much, so I steered Mrs. HDM down Middle Street in Weymouth to the Middle Street Mini Plaza.

That’s at # 407 Middle Street to be exact and it’s the location of the Boston area’s ONLY genuine Chicago Hot Dog joint, Windy City Eats.

The piazza looked inviting, but a tad too damp on this day.
We decided to dine indoors. When we got inside, we found owner and proud Chicagoan Grady Carlson stocking up for the lunch rush. His wife, Sen, who co-owns the joint, was working away in the kitchen. Unfortunately, Sen’s photo was a tad blurry, so she’s listed as “camera shy” today (I have to get a better camera).
According to the Windy City Eats website:
Grady Carlson grew up in Evanston, Illinois on the north side of Chicago. Grady Moved to Los Angeles California after serving in the Army and met and married his wife Sen. We have no idea how Grady tricked Sen into dating him, let along marrying him. Let’s just say Grady is a lucky man.

Sen and her sister owned a frozen yogurt shop in Los Angeles. A few years later Grady and Sen had a son, Kamden (check out Kamden’s Korner on the menu). With Kamden’s arrival Sen and Grady decided to move to Weymouth to be closer to some of their family.

The move to the Boston area allowed Grady to start a new venture, fulfilling a life long dream of opening a Chicago Style Hot Dog Stand.


Grady was the first graduate of Hot Dog University who planned on opening a brick and mortar hot dog joint- the course is primarily for folks who want to open a hot dog cart. In the “gee, it sure is a small world” category, the Hot Dog University professor was Grady’s brother’s high school science teacher! Vienna Beef, the maker of the true Chicago Dog, has since taken control of Hot Dog University and brought it “in house” as the training grounds for wanna be Chicago Hot Dog stand operators worldwide.

Even without all this Chicago related background information, it would be easy to tell Grady’s from Chicago based on the prominent display of a certain field named as a memorial to servicemen killed in war which happens to be the home of a certain group of gridiron gargantuans who periodically pummel opponents into a perturbed and petrified preponderance of perpetual presupposed profligation; a team more commonly known as….


The photo of Wrigley Field confirms Grady’s “north side” roots.


You can’t help but notice all the dollar bills taped to the walls (we actually found currency from 6 countries). When Grady first opened up 2 years ago, a customer asked to tape a dollar bill to the wall so his friends would know he had sent them to the right place. The idea just kind of took off: there are dollar bills on every wall… 

…on the counter…
…on the ceiling (looks like there was a cheapskate here recently)….

…even on the chairs!

I HAD to get into the act!

Sorry for the digression, this aint a numismatics story, it’s Hot Dog Stories.
Before we get to the day’s meal, I feel compelled to offer a bit of history about the Chicago dog. There are several key ingredients that make up a “true” Chicago hot dog. The first and foremost is the Vienna Beef hot dog.
Vienna Beef has been making hot dogs in Chicago in the same spot since 1893. A guy by the name of Henry Davis who was the Vice President of sales was an instrumental player in the development of the thousands of hot dog stands that populate Chicagoland. It is considered to be THE Chicago hot dog (even Cubs and White Sox fans can agree on that).

A true Chicago dog is served on a poppy seed bun and is topped with bright green relish (blue dye #1 is the key ingredient), chopped onions, tomato wedges, sport peppers, a dill pickle spear, mustard, and celery salt. Having a dog this way is called “dragging it through the garden,” a phrase and a hot dog topping methodology made popular during the Great Depression. Folks would order a ten cent hot dog and make it a complete meal by “dragging it through the garden.”

Windy City Eats uses the real stuff for their dogs, they’re 100% authentic. You can purchase the condiments and the Vienna beef dogs right in the store if you want to make your own Chicago Dogs at home.

True to form in any self respecting Chicago Dog joint, there wasn’t any ketchup in sight!
After all this talk, we were ready to check out the menu. In addition to hot dogs, you can order Polish sausage, Italian sausage, Italian beef, pastrami, meatball subs, cheese steak, cold cut sandwiches, hot wings, chili, onion rings and fries. Yummy stuff!
There are daily specials too.
Grady tried to entice me with Vienna’s newest creation, the jalapeno cheddar dog.
We were here for the real Chicago Dog, and Mrs. HDM wanted to try another bit of Chicago cuisine, chili cheese fries (it’s the closest thing to poutine in these parts).
Look at that! The fries are topped with chili, cheese and onions!
We also got a couple of Chicago Dogs and two cream sodas to wash ’em down (cream soda is my vintage of choice for accompanying hot dogs-at least when a cold beer isn’t available). Good lookin’ dogs, eh?
The architecture of these dogs bears closer inspection.
Poppy seed bun, CHECK. Vienna Beef dog, CHECK. Tomato wedges, CHECK. Onions, CHECK, Dill pickle spear, CHECK. Mustard, CHECK. Sport peppers, CHECK. Bright green relish (it looks like lime jello fercryinoutloud), CHECK. Celery salt, CHECK. OK, it’s a real Chicago Dog, guess I can go ahead and…..
As usual, Mrs. HDM wanted no part of having her picture taken while eating.
This was indeed a treat! The chili cheese fries were yummy, not poutine yummy, but excellent nonetheless. The hot dogs were exceptional. I have had the real Chicago Dogs in Chicago, and I have had “Chicago Style”  dogs in other establishments: these dogs oozed with authenticity. A Chicago Dog really is a flavor explosion that must be experienced. The competing textures and spiciness of the sport peppers combined with the heartier dill pickle, tomato and onions make for quite a treat. The celery salt somehow pulls it all together as a kind of “dressing.” Chicago dogs must be on your culinary “bucket list.” For you native Chicagoans in the Boston area: if you have a craving for a taste of home, Windy City Eats is tailor made for you.
After such a delight, I was hankering for dessert. Like a good, native, Chicagolander, I opted for a Vienna “Maxwell Street” Polish Sausage! That’s a Polish Sausage with grilled onions and mustard.
And I CHOWED DOWN again!
This was very good too. A Polish sausage is milder than the ubiquitous Bostonian Italian sausage. It’s more like a mild kielbasa. I would have anything I ordered today again. The authentic Chicago Dog makes Windy City Eats a must eat establishment for Chicago natives and hot dog aficionados alike.
Windy City Eats gets TWO THUMBS WAY UP from the Hotdogman! Mrs. HDM gives it TWO THUMBS UP too, but she was “all set” with any more pictures on this trip!
Windy City Eats is open Tuesday through Saturday 11:30 AM-8:30 PM, and  Sundays Noon-7PM. They’re closed on Mondays.
You must put Windy City Eats on your list of dining options. Make sure you tell Grady and Sen “Mr. and Mrs. Hotdogman (and the ghost of Mayor Daley) sent me!”

Windy City Eats on Urbanspoon


  1. Stopped by today, for the 2nd time in 3 days, and had an original Chicago-style “Italian Beef”, very good, very authentic, no where else in New England are there anything like it.

    Usually in this part of the country, they have “Cheese-Steaks” or something that looks like a “Philly-Steak”, but nowhere in New England have I found an Italian Beef like they have here at Windy City Eats in Weymouth. 🙂

    I had a “Chicago Hot-Dog” last Saturday, next time, I’ll try the “Maxwell Street Polish Sausage” with onions, the only way they should be served.
    For 30 years I lived in the North side of Chicago, 2 miles from Wrigley Field on Sheffield and the DePaul neighborhood but,
    I and all my friends were White Sox fans and would drive to the South Side in the 1980s to the games at Comiskey Park and just had to stop at the corner of Maxwell and Halsted to have those famous Polish Sausages on the way back home to the north side. 🙂
    In those days, it was called “Jew-Town” because of the bargains you could find in the area on Sunday mornings. I think today it’s (politically-correct) called Maxwell Street Market or something like that. 🙂

    I met Rob today and he explained the difference between a wieners and a franks. 🙂


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