Travel by Mouth: Eating My Way Through Chicago’s Most Famous Foods

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Travel by Mouth: Eating My Way Through Chicago’s Most Famous Foods

“Get Out There” is a column for itchy footed humans written by long-time Paste contributor Blake Snow. Although different now, travel is better than ever. Today we travel to Chicago by mouth.

Chicago is America’s third largest urban center and, in terms of original food, also the country’s third best culinary city (after New Orleans and New York). Drool-inducing deep dish pizza, topping-rich Chicago dogs, dripping wet Italian beef sandwiches, the birthplace of brownies, and several other tasty treats are all worth visiting for. Which is precisely what I did this spring. Will travel for food! 

Here’s everything you need to know from my recent Chicago food crawl, which pitted the Windy City’s top-rated restaurants against each other. And the winners are…

Deep dish: Giordano’s vs. Lou Malnati’s

Chicago deep dish pizza weighs on you in a good way. When in ChiTown, there are two institutions that tourists flock to. Both are great. But one is more memorable. That would be Giordano’s, thanks to its thinner, saltier, and softer crust, significantly taller and deeper stuffings, and overall richer marinara and more generous cheese portions (not to mention picture perfect pulls). 

Locals will tell you that Lou’s has more authentic butter crust, which may be true. But their pie-like crust was blandly under-seasoned, too thick, and too hard to cut with a fork (you cannot handle these mammoth things). Lou’s has a better dining room and faster service though. 

Winner: Giordano’s.

Chicago deep dish


Chicago dog: Portillo’s vs. Devil Dogs

Chicago has more hot dog restaurants than McDonald’s, Wendy’s, and Burger Kings combined. That’s because Chicago dogs are the best in the world from a taste, texture, and flavor profile. Loaded with over a half a dozen toppings, these babies are “run through the garden” and mouth-watering delicious. 

If I’m really being honest, I didn’t have a bad dog from the four places I tried. But of the two top-rated locations, I prefer the newer Devil Dogs over the tried and true Portillo’s. The former has better bite and fresher combinations, like the fantastic Elote-style Chicago dog. While the latter is still solid, the wiener was a little too mushy against all those crunchy toppings. 

Winner: Devil Dogs.   


Italian beef: Mr. Beef vs. Al’s #1

Although they’ve been a Chicago staple for decades, Italian beef sandwiches didn’t get nationally noticed until two years ago, after The Bear became the second most popular TV show in America. Nevertheless, these thinly sliced cheap cuts of beef are encased in French bread, topped with sweet and sour peppers, and fully dunked in greasy thin gravy drippings—the wetter the better. 

Mr. Beef, which The Bear is based upon, beats Al’s # 1 Italian Beef in both attitude and flavor. The Soup Nazi vibe is a little intimidating, though. No bathrooms. Cash only. Long lines well past noon. I was scared to ask for a vegetarian option for my daughter (they obliged and it was fantastic) and a knife (“No”). But the “mean but still nice” service was just as good as the sandwich. What an experience. Al’s, on the other hand, was really #3, because even Portillo’s serves a better Italian. 

Winner: Mr. Beef. 


Birthplace of brownies: Palmer House vs. Sweet Mandy B’s

Like Italian beef, it wasn’t until recently that the world recognized Chicago as the inventor of the beloved brownie. Invented in 1893 by the Palmer House Hotel for the Chicago World’s Fair, you can enjoy the same brownie today from the original  lobby restaurant of the longest running hotel in America. 

So how does it taste? Richly fantastic! The original Palmer House brownie has less flour and more melted chocolate to create a fudgier, less bready, and less cake-like consistency than modern brownies are known for. For comparison, I tested the indulgent, berry-topped Palmer against the traditional fudge brownie from Sweet Mandy B’s. I love ‘em both for different reasons—the former for being more indulgent; the later is more balanced. You can’t go wrong, though. Brownie lovers will enjoy both, and I thank the heavens that Palmer House invented this classic dessert. 

Winner: Tie.


Bonus treats: Cake shakes, sweet and savory popcorn, creamier cheese cake

There are a few other notable Chicago creations worth considering: Garrett “Chicago Mix” caramel and cheese popcorn, Eli’s “creamier” cheese cake (that ships nationwide), and Portillo’s awesome Cake Shakes (both lemon and chocolate). I also went nuts for Devil Dog’s real fruit banana-strawberry shake and Lou Malnati’s magical Chocolate Obsession, which is a brownie bite-filled brick of chocolate mousse, layered on a chocolate bar, and drenched in ganache. It’s death by chocolate. 

ProTip: If you visit only one Chicago restaurant, make it Portillo’s & Barnelli’s, which is like a “greatest hits” of famous foods, including Chicago dogs, cake shakes, Italian beef, and chop salad. No deep dish though.


Blake Snow contributes to fancy publications and Fortune 500 companies as a bodacious writer-for-hire and frequent travel columnist. He lives in Provo, Utah with his wife, five children, and one ferocious chihuahua.

Main photo by TNVWBOY ,used under CC 2.0 license.

Other photo by Blake Snow.

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