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Embark on Chicago-style food-tasting adventure

Embark on Chicago-style food-tasting adventure

by Nicolas Howard
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Table of contents

  • 1. Grab a donut to start off the day
  • 2. Start your culinary expedition with Arancini Pomodoro
  • 3. Windy City Gyros for your Mediterranean fix
  • 4. A Chicago-style hot dog for a classic
  • 5. Italian Beef Sandwich for the savory bite you crave
  • 6. Jibaritos for a one-of-a-kind experience
  • 7. Deep dish pizza for Chicago's most famous dish
  • 8. Sample a Gym Shoe for the most bizarre food in Chicago
  • 9. Japanese Round Tofu at Chicago's best Asian restaurant
  • 10. Italian gelato to cap off a perfect day
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Chicago is a city in the American Midwest with a rich culture and plenty of diverse, delicious food offerings. Organized as a town with a population of about 200 people in 1833, Chicago has become a sprawling metropolis. In nearly 200 years since its settlement, the city has attracted people from all backgrounds by offering a variety of jobs and amenities. The wide array of people that have lived in Chicago over the centuries has created some of the most scrumptious food that America has to offer. Discover the city's all-time favorites and eateries that have pushed culinary boundaries with you in mind.

1. Grab a donut to start off the day
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D&D's Place
#2 of 3298 restaurants with desserts in Chicago, USA
8324 S Kedzie Ave, Chicago, Illinois, USA
Closed until tomorrow
Doughnuts
Doughnuts

Doughnuts are sweet ring-shaped treats that are typically made with flour dough and then deep-fried. These sweet round snacks can also be coated in sugar, chocolate, or maple glazing.

Plenty of chains sell boring, ordinary donuts, but The Donut Fest 2018-2020 winner D&D's Place is on an entirely different level when it comes to their donuts. Their fresh, homemade donuts are absolutely divine. The magic begins when the donut dough is dropped into the fryer, where it sizzles to perfection. The old-fashioned buttermilk cake donuts are then topped with any topping that could possibly be imagined. One bite of a donut from D&D's Place, and you may never buy a donut from a chain restaurant again.

On a family vacation to Chicago? Planning to take the kids to Chicago Zoo? Then, a visit to D&D's Place is the ideal way to start off a great day. 

2. Start your culinary expedition with Arancini Pomodoro
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Eataly
#961 of 16159 restaurants in Chicago, USA
43 E Ohio St, Chicago, Illinois, USA
Closed until tomorrow
Arancini
Arancini

They are deep-fried rice balls stuffed with mince or meat, tomato sauce, cheese and spices and coated with bread crumbs. Arancini are traditional Sicilian food whose invention traces back to the Arab rule in the 10th century. The name means 'little orange' because of their color and shape.

Anyone on a food-tasting tour of Chicago could spend several days trying out all of the food at Eataly alone. However, Eataly's Arancini Pomodoro will definitely impress those interested in sampling a stellar starter. These crispy risotto croquettes are made of carnaroli rice, tomato sauce that features plenty of delicious Italian herbs, and pecorino romano cheese. After searing these tasty treats to perfection, they are ready to be served. Taking a bite of Arancini Pomodoro is a heavenly experience, as the crispy exterior gives way to the warm, gooey interior. We can thank the ancient Sicilians for this perfect snack; the southern island is known for combining simple ingredients into tasty recipes. As a result, Arancini are inexpensive, easy to make, and ready to eat on the go, calling only for rice and a few seasonings. 

With their authentic Italian flavors and homemade pasta, stopping at Eataly is a must for anyone looking to try some of the best cuisines that Chicago has to offer. 

3. Windy City Gyros for your Mediterranean fix
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Windy City Gyros
#1189 of 8847 fast food in Chicago, USA
3932 N Broadway, Chicago, Illinois, USA
Open until 3AM
Gyros
Gyros

Gyros are basically wraps in Greece that are filled with large pieces of grilled meat, onions, tomato, lettuce, fries, and other optional ingredients that are rolled in a pita. Gyros are normally made out of pork, though other meats like lamb, beef, or chicken are also used.

Gyros made their American debut in Chicago in the 1960s and have been beloved by Chicagoans ever since. Dozens of restaurants serve up this portable Mediterranean dish, but Windy City Gyros is hard to beat. Making a gyro begins when the meat is sliced off of the rotisserie. Next, the famed gyros are neatly wrapped in pita bread, and inside your gyro, you can expect beef, chicken, lettuce, tomato, and tzatziki sauce-scrumptious!

Were you looking for a Chicago-style gyro with a modern twist? You can't go wrong with this savory dish with a side of fries and salad of your choice at Windy City Gyros.

4. A Chicago-style hot dog for a classic
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Portillo's & Barnelli's Chicago
#1196 of 8847 fast food in Chicago, USA
100 W Ontario St, Chicago, Illinois, USA
Open until 1AM
Hot dogs
Hot dogs

A hot dog or sausage in a loaf - this dish is the embodiment of simplicity. Therefore, probably, it has become so popular all over the world. And although it is not particularly refined, it is prepared in various parts of our planet. The history of hot dog originates back in the Middle Ages: it is believed that the first sausages appeared in Frankfurt in 1487. However, the turning point in the "career" of hot dogs is associated with mass emigration from Europe to the US at the end of the XIX century.

Look no further than a Chicago-style hot dog from Portillo's Hot Dods for those needing a quick, portable meal. This fast food chain started in the Chicago area and has served up authentic Chicago hot dogs ever since. This version of classic American food ups the ante on the typically boring sausage in a hot dog bun. It all starts with a hot dog made of Vienna beef-this specialty hot dog is cooked in hot (but not boiling) water. After the hot dog has been prepared, it is added to a warm bun adorned with poppy seeds before it is smothered with toppings. Sweet pickle relish, a dill pickle spear, diced white onion, sliced tomato, celery salt, sport peppers, and of course, yellow mustard provide the perfect combinations of sweet, zesty, and spicy on this classic Chicago food. 

Visit Portillo's Hot Dogs to feel like a real Chicagoan!

5. Italian Beef Sandwich for the savory bite you crave
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Al's #1 Italian Beef
#988 of 1975 Italian restaurants in Chicago, USA
548 N Wells St, Chicago, Illinois, USA
Closes soon: 12AM

The Italian beef sandwich is another dish that traces its origins back to the Windy City. Originally thought to be created around 1900 by Italian Americans who worked as laborers in Chicago, this sandwich came from humble beginnings. Several decades later, the Italian beef sandwich began to gain recognition. In the late 1930s, Al's #1 Italian Beef helped to propel this sandwich to stardom, and customers can still enjoy this famed dish at Al's today. The sandwich is created when Italian bread is loaded with roast beef that has been slow-cooked for hours, practically allowing the meat to melt in your mouth. Add peppers and a rich au jus sauce, and you've got yourself an irresistible Italian beef sandwich at Al's #1 Italian Beef.

6. Jibaritos for a one-of-a-kind experience
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Jibaritos Y Mas
#590 of 1925 steak restaurants in Chicago, USA
3400 W Fullerton Ave, Chicago, Illinois, USA
Closed until tomorrow

Jibaritos are the new kid on the block, so to speak, when it comes to beloved Chicago foods. A jibarito is a Puerto Rican dish popularized in Chicago in the 1990s and has been wildly favored in the Windy City ever since. Jibaritos combine protein such as beef or chicken with lettuce, tomatoes, and savory garlic mayo and insert this filling between two crispy, flat plantains that are seared to perfection. The crunch from the plantains coupled with the tender filling leaves customers licking their fingers and wanting more. There are several places to find jibaritos in Chicago, but Jibaritos Y Más is among the best. 

7. Deep dish pizza for Chicago's most famous dish
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Lou Malnati's Pizzeria
#5 of 2289 pizza restaurants in Chicago, USA
439 N Wells St, Chicago, Illinois, USA
Closed until tomorrow

Several restaurants in Chicago are known for serving up their takes on deep dish pizza. However, ask Chicagoans which version is best, and many will point you in the direction of River North — Lou Malnati's Pizzeria. The scrumptious, buttery crust of a deep dish pizza is made by rolling out the dough and lining a pan. Much thicker than a typical pizza, deep dish pizza is composed of a thick crust topped with several layers of tangy tomato sauce, mountains of cheese, and any toppings your heart desires. When the pizza is brought out to your table, you will immediately be captivated by the smells of cheese and sauce paired with Italian spices. As you remove a slice of pizza from the pan, the cheese will stretch to unbelievable lengths as the warm, gooey slice is heaped onto a plate. One bite of this masterpiece will allow you to understand why it has gained such immense popularity, as the combination of the aromatic sauce, buttery crust, and savory cheese will keep you coming back for more to Lou Malnati's Pizzeria.

8. Sample a Gym Shoe for the most bizarre food in Chicago
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Stony Sub
#1581 of 8847 fast food in Chicago, USA
8440 S Stony Is Ave, Chicago, Illinois, USA
Open 24 hours

Though it may not have the most appetizing name, a gym shoe gives the Italian beef sandwich a run for its money when it comes to the favorite sandwich of Chicagoans. Originating on the south side of Chicago, this dish is a delightful union of an assortment of seemingly random ingredients that come together to form a succulent sandwich miraculously. The utterly unique gym shoe sandwich takes a grilled sub made of Italian bread and stuffs it until it's overflowing. The filling is a glorious collection of three different types of meat (corned beef, roast beef, and gyro meat), swiss cheese, onions, peppers, tomatoes, giardiniera, and tzatziki. The result is a seemingly chaotic but irresistibly delicious sandwich. Of course, a collection of places serves up terrific gym shoes, but a Chicagoan favorite can be found at Stony Sub

9. Japanese Round Tofu at Chicago's best Asian restaurant
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Grand Palace
#2136 of 16159 restaurants in Chicago, USA
225 W 26th St, Chicago, Illinois, USA
Closed until tomorrow

The Grand Palace is considered by many to be the pinnacle of Asian cuisine in the Windy City. Providing genuine Asian dishes from a variety of different cultures, it is hard to argue that Grand Palace is the best of the best. While tofu may not sound like the most appetizing dish, a taste of the Japanese round tofu with mixed mushrooms will show you just how exciting tofu can be when prepared properly. Marinated with a wealth of Asian flavors, the tofu steals the show as it absorbs all of the irresistible tastes in this dish. Paired with tender mixed mushrooms, this meal is the optimal union of savory and umami flavors. 

Check out The Grand Palace for incredible tofu and more.

10. Italian gelato to cap off a perfect day
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Massa Cafe Italiano
#52 of 7866 cafes in Chicago, USA
7434 W North Ave, Elmwood Park, Illinois, USA
Closed until tomorrow
Gelato
Gelato

It's traditional Italian ice cream acknowledged to be one of the best frozen desserts in the world. Gelato was introduced by the Italian chef in Paris in 1600. This dessert contains 3.25% milk and sugar. It has a lower percentage of fat and less air, that's why it boasts of a richer texture.

Considering the Italian influence on the city of Chicago, it should come as no surprise that the gelato offered throughout the city is second to none. Of course, there are lots of places where great gelato can be found in the Windy City, but for those who want exceptional gelato, Massa Café Italiano excels with its heavenly flavor voted “best in America” during the 2016 Gelato World Tour. The milk, berries, and other yummy ingredients are churned to the optimal level to create a thick, flavorful dessert. The smooth, creamy consistency of their gelato will keep you yearning for more, and with a variety of different flavors, the possibilities are seemingly limitless.

After a long day of exploring Chicago, a gelato treat is an ideal way to finish off the day in a relaxed setting at Massa Café Italiano.

Chicago's cuisine has had a significant influence on the city and on America as a whole. The Windy City has spawned some of the most delicious dishes that can be found in the United States, and a visit to Chicago really would not be complete without stopping at some of its famed restaurants. Best of all, since Chicago has been so heavily influenced by the diverse immigrants that settled the city, there are dishes for any preference imaginable. So, what's holding you back? Travel to Chicago and taste for yourself the best that the Windy City has to offer!

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