Chicago is known for its three signature food items: (1) stomach-expanding deep dish pizza; (2) savory Italian beef sandwiches piled high with beef galore and soaked in au jus; and (3) Chicago-style 'dogs, loaded with special toppings and condiments. On my recent visit to Chicago, my quest was to try the "best" of all of these types of food, and weigh in with my own opinion. After some guidance from Dylan of Eat, Drink, and Be Merry, who recently visited Chicago, I set out on my quest.
First, where are the best hot dogs in Chicago? I attempted to answer this question by visiting four reputable hot dog eateries, in less than two days.

THE WIENER CIRCLE
My first visit for hot dogs was The Wieners Circle, where you can allegedly get a serving of "sass," banter, and attitude with your hot dogs. Rumor has it, that if you give the female cashier $20 and ask for a "chocolate (or vanilla) milkshake," depending on the race of the server, she will "flash" you.
That is terrible for so many reasons.

Now, I did not ask for a milkshake, but I did order two "Vienna red hot" dogs, one with a slathering of melted nacho cheese.

While the wieners tasted like classic hot dogs, I loved the Chicago touches of (1) the poppy seed encrusted bun, (2) the fresh relish made with chopped onion, (3) the fiery and acidic banana peppers, (4) the elongated wedge of dill pickle, (5) the cooling slices of beefsteak tomato, and (6) a sweet dusting of celery salt.
Also, Wieners Circle's fluffy fries were steaming hot, and had a golden-brown and crispy shell.

Overall, the hot dogs and fries received a "B+" in my book. A respectable grade for a respectable hot dog establishment.
SUPERDAWG
Next, I visited SuperDawg, a drive-in fast food joint from the bygone period of yesteryear. Upon arriving, I was immediately entranced. I loved the assembly line of industrious workers, the animated hot dog mascots, the amazing variety of 1950s soda shoppe drink selections, and the whimsical hot dog packaging and decor. Similar to Wieners Circle, SuperDawg's crinkle cut fries were perfectly fried, with a crisp and seasoned shell and soft potato interior.

The dogs from SuperDawg came with all the Chicago fixings, including a dill pickle wedge, mustard, and banana peppers. As for the relish, I was truly impressed by the zesty, fresh, and bright flavors of their homemade version. Were there bell peppers in the relish? It certainly looked like it, and it tasted heavenly. Along with the classic Chicago hot dog ingredients, I enjoyed the large wedge of brined green tomato. I found the quality of the hot dog to be far better than the Vienna red hots served at Wieners Circle, for I could taste heavy undertones of beefiness and there was more of a substantial and hearty texture to the hot dog.

Although I was a little disappointed by the way my hot dog and fries were mashed inside a small brick-sized box, I would say, "A" for this super dog.
PORTILLO'S
Third, I visited Portillo's, and enjoyed the hot dog there, as well. Portillo's is a fun restaurant, with a unique and old-fashioned style of service and decor. As for the meaty dogs, I found them quite similar in flavor and in topping ingredients to Wieners Circle, with the right proportion of condiments and fixings, and a warm and delectable meat wiener. So a healthy "B+" for Portillo's.

(As you can tell, I am running a little low on words to describe the hot dogs.) But I do want to note with jubilation that Portillo's has opened two locations outside of the State of Illinois and in Southern California, so if you live in So Cal, go forth and take advantage of this Chicago eatery!
HOT DOUG'S
Finally, I visited a gourmet and more upscale version of a classic hot dog stand in Chicago, Hot Doug's, which is self-entitled as "the Sausage Superstore and Encased Meat Emporium." Hot Doug's does not only serve hot dogs, but gourmet sausages. Doug Sohn, the owner and namesake of the eatery, took it to a whole 'nother level. And actually, Doug of Hot Doug's is really hot.

Everyone and their mama has likely heard about Hot Doug's, especially after Anthony Bourdain featured Hot Doug's on one of his No Reservations episodes. Because of its immense popularity, you must be prepared for a long wait in a long line. And you will likely have to brave the relentless Chicago weather. For me, after torturously waiting over an hour in the sleet and frostbite-inducing and skin-shredding Chicago wind, I arrived inside, drenched with rain and sporting raw and chapped skin lesions.
Doug runs the counter and the cash register. Based on Doug's recommendation, I ordered three types of "encased meats." I enjoyed (1) a bacon and cheddar elk sausage with Goose Island Pere Jacques mustard and Madrigal cheese, (2) a chardonnay-infused rattlesnake sausage with sweet Peppadew dijonnaise and green peppercorn Montsegur cheese, and (3) a jalapeno and bacon duck sausage with blood orange mustard and Chaubier cheese drizzled with honey.


Okay, I am going to be vulnerable with you all, and admit to a sin that I committed that no food blogger should ever do. I wolfed down the delicious sausages and did not adequately document the sausages. By the time I eventually reviewed my pictures, I was pretty flabbergasted as to which sausage was which. I also ate so fast, that I do not actually remember that much about my wonderful meal. I do remember, however, that it was "wonderful." Finally, I ordered "to go," and took some messy pictures because the sauce from the 'dogs had smeared all over the wrappers. But I know you will forgive me. If not, I guess I will have to eat there again.
Nevertheless, I do remember some key characteristics about the sausages and their toppings. The elk sausage was surprisingly tough, dry, and resistant to the bite. Because of the texture, I thought that Doug did a particularly good job pairing the elk sausage with strong spices, a potent mustard, and a robust cheese. I thought the rattlesnake was interestingly tender and sweet, and I loved the spicy, fiery aroma from the peppercorns. Finally, the duck sausage possessed a penetrating cumin aroma, and really stood wonderfully on its own.
Best of all, on Fridays and Saturdays, you can partake of Doug's duck fat French fries, which are light, airy, and ethereal. They taste just like regular fries, but have a uniquely light feel to them. French fries deep-fried in duck fat? Oh man, I am in heaven (or will die and go to hell soon)!

The interestingly gourmet twist on the classic Chicago dog was very convincing for my palate. Hot Doug's scored an "A" from me on its report card.
Now that I finished my excellent hot dog adventure, and have emerged with a clear victor in mind, I will share about my journey in seeking an answer to the baffling question of where to find the best Italian beef in Chicago. That question led me to two places.
PORTILLO'S
My first experience with Italian beef was at Portillo's, the same place where I also ordered an enjoyable hot dog (see above). I actually visited Portillo's with a few Chicago natives, and they gave me a few pointers on how to order Italian beef sandwiches in Chicago. First, you must order them with peppers. Second, you must also order them dipped in the roast beef jus. And that is exactly what I did. (Oh, and check out this great Italian beef website for more tips on how to order.)

When I unwrapped the soggy foil-lined paper, I was quite overwhelmed with the amount of beef stuffed inside what was once crusty bread. Everything was in disarray. However, one bite, and I was smitten.

I loved (1) the rich oregano-flavored beef broth which had been soaked into the bread, (2) the soft pieces of celery, onions, and carrots that had been slow cooked and shoved inside the beef sandwich, (3) the slippery and tender slices of beef, and (4) the giardiniera relish made of pickled sport peppers and carrots. The toothsome slices of roasted beef were full of flavor from the Italian spices and coated with a perfect amount of jus (and grease). Definitely an "A" grade.
AL'S BEEF
After my experience with the Italian beef sandwiches at Portillo's, I had high hopes for what was lauded as the "#1 Italian beef" in the City of Chicago, Al's Beef.

But my hopes were not to be realized. Unlike the slices of beef from Portillo's, I found Al's sandwich to be lacking in inherent moisture. The meat seemed to be cooked beyond recognition, and was more akin to an overcooked chipped beef sandwich, than a nicely sliced roast beef sandwich. It seemed as if the juices had been completely drained from the beef, and Al simply dunked the beef in jus, hoping to reconstitute it. Also, the mushy bread was saturated with the oddly flavored jus. I found the jus to be overpowered with the strong essence from cloves. Sorry Al, but you are a distant second to Portillo's according to my experience at your place. I hate to be harsh, but I would give you a "C."
So there you have it, my take on the best hot dogs in Chicago and the best Italian beef sandwiches in Chicago. What are your thoughts about Chicago's best? Also, stay tuned for my take on the best deep dish pizzas in Chicago, next!