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The 5 Best Guilty Pleasure Eateries in Chicago

Chicago has perfected guilty pleasure foods. Sure, the Windy City may be a metropolis with countless elegant dining options. But its heart and soul are in foods like Italian beef sandwiches, deep-dish pizzas, and hot dogs.

The city’s best junk food joints are often some of its oldest, most established eateries. But in a place as big as Chicago, you can satisfy pretty much any food craving.

Join us as we dive into Chicago’s best guilty pleasure restaurants.

Let’s go!

Hungry woman peeking out of behind table and looking at doughnut, one of the guilty pleasures found in Chicago
The pleasure overrides the guilt at Stan’s Donuts

What’s Guilty Pleasure Chicago Food?

Everyone has a guilty pleasure or two. It’s those things you love in spite of their generally bad reputation. Whether it’s cheesy songs from past decades, cringe-worthy movies, or corny romance novels, we all have something like this we enjoy occasionally.

But certain food can hit both the pleasure and guilt feelings inside all of us. You may consider these dishes comfort foods. They’re the snacks or meals you can’t eat every day. Is there anything better than a big plate of greasy pizza, sugary dessert, or starchy potatoes at the end of a long week?

Big cities like Chicago are full of guilty pleasure eateries. The Windy City boasts more than 20,000 restaurants, many of them specializing in junk food and delicious snacks. Here are five of the best places to indulge yourself on your next visit.

Find out if The Windy City is a good destination for you with 5 Reasons to Avoid Chicago.

#1 Stan’s Donuts

The original Stan’s Donuts opened in Los Angeles in the 1960s. But thanks to the joint efforts of the owner of Stan’s Donuts and a local baker, a Chicago location opened in 2014. The spot quickly became a favorite with Chicagoans who needed breakfast on the go. But this place isn’t for health nuts!

The donut shop offers all the classic options like glazed and cake donuts, Bismarks, eclairs, cinnamon rolls, and crullers. But they offer even more decadent options too.

You can also order different styles of pockets, which are donuts topped with candy or frosting and filled with cream. And then there’s the Le Stan Croissant, a croissant-style donut topped with powdered sugar. They even serve popular cake-inspired flavors like red velvet.

This Chicago guilty pleasure definitely isn’t an everyday treat. But if you’re ready for a diet cheat day, you have to check out Stan’s Donuts.

#2 Portillo’s

Portillo’s has satisfied the junk food cravings of Windy City residents since 1963. The famous hot dog joint was originally a small stand called The Dog House. Eventually, the restaurant became known as Portillo’s, named after its founder Dick Portillo. Today Portillo’s has over 70 locations across the U.S. 

The menu is chock full of Chicago’s best guilty pleasure foods. You can try an Italian beef sandwich or a Chicago-style hot dog, two of the city’s most iconic dishes. Portillo’s also serves classic fast food options like burgers, fries, and milkshakes. Their best-known dessert is a milkshake that includes chunks of real, homemade chocolate cake.

If you’re counting calories, you can choose between several salads on their menu. But let’s be real, who’s ordering those when visiting Portillo’s?

#3 Fatso’s Last Stand

Ah, Fatso’s Last Stand. This burger and hot dog stand offers next-level junk food. But the ingredients are fresh and delicious. You won’t find mass-produced menu items here.

You can choose any number of Fatso burgers, but the most tempting one is the Ooey Gooey, with a patty stuffed with cheese. And Samuel’s Double Fatso Extreme is a half-pound cheeseburger served with bacon and a fried egg.

If burgers aren’t your thing, try the Monster Combo, which includes a giant Italian beef sandwich with all the fixings. Then there’s Fatso’s famous mac and cheese, which you can order with meat for an additional charge.

And we can’t forget to mention the boozy milkshakes. You can choose from flavors like s’mores, mudslide, or banana cream pie. Fatso’s Last Stand is truly a guilty pleasure in every sense of the term.

#4 Lou Malnati’s

Lou Malnati’s is one of the Windy City’s most beloved establishments. Lou, the restaurant’s founder, began making Chicago-style pies in the 1940s. But by 1971, he and his wife opened their first restaurant, with more locations to follow before Lou passed away in 1978. The Malnati family still runs the restaurant to this day.

Their specialty is deep-dish Chicago-style pizza, but they offer many other items too. Fried calamari, toasted mozzarella sticks, and chicken wings are just a few of the appetizers on their menu.

If you’re in the mood for decadent pasta, try the Chicken Louie or Penne ala Malnati. And you’ll want to leave room for dessert. Choose from tiramisu, cookies, or Chocolate Obsession, a treat made with chocolate mousse, ganache, and brownie batter. You’ll probably want to wear your stretchiest pants to visit this Chicago guilty pleasure.

Can’t get to Malnati’s? Here’s How to Bake Deep Dish Pizza on Your Grill.

Grilled Macaroni and Cheese Sandwich is certainly a guilty pleasure in Chicago/ photographed on Hasselblad H3D2-39mb Camera
Grilled Macaroni and Cheese Sandwich? Yes, please!

#5 Cheesie’s

Cheesie’s is a cheese lover’s dream come true. This Chicago guilty pleasure opened in 2011 when founder Chris Johnston decided the city needed a restaurant dedicated to grilled cheese sandwiches. Business was so good he moved to a more prominent location within the first year.

Today Cheesie’s has three stores and a food truck. The restaurant is still owned and operated by Johnston and his family.

Cheesie’s sandwiches are true masterpieces. The Tenderizer comes with two kinds of cheese, chicken tenders, and a special sauce. Then you’ve got the Mac, stuffed with macaroni and cheese and served with tomato soup sauce. One of the most decadent items has to be the Frenchie, featuring three kinds of cheese, fries, bacon, and chives.

Desserts like deep-fried PB&J sandwiches and stuffed cinnamon rolls round out the menu. Cheesie’s isn’t for the faint of heart, so make sure you’re hungry when you go!

Make it a foodie adventure with Chicago Food Crawls: Touring the Neighborhoods One Bite & Libation at a Time.

Chicago is Full of Guilty Pleasure Foods

With life’s many stresses, we all deserve a guilty pleasure sometimes. For many of us, comfort food is an integral part of life.

Make sure to treat yourself on your next trip to Chicago. With so many delicious options to choose from, you may want to add a few extra days to your stay. You wouldn’t want to miss out on a Fatso burger or a stuffed grilled cheese!

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