5 Truly Great Chicago Sandwiches | Best Breakfast in Chicago

October 21, 2019

chicago sandwiches | Best Breakfast in Chicago

Whether you’re new to the city or grew up here, you know Chicago is all about her food.

Sure, you get a kick out of the glittering nighttime cityscapes, especially from the top of the Sears (err…Wilson) Tower. A day on the pier—Navy Pier—brings the lake up close. Or, far away if you view it from the top of the Centennial Wheel.

But it’s the food that warms your heart in this city.

Those iconic Chicago sandwiches. Some you’ll only discover if you venture into certain neighborhoods. You’ll find others at some of the most popular Breakfast & Lunch in town.

Here are 5 of the greatest Chicago sandwiches. We’ve even included the ingredients, and for some, a little history.

1. Now That’s Italian

If you’re looking for a Chicago icon in the form of a sandwich, look no further than the Italian Beef. Don’t look too far because once you’re out of the Chicago area, it’s hard to find a proper beef.

You can thank Chicago’s Italian immigrant community for this sandwich. It’s a simple working man’s sandwich likely enjoyed by stockyard workers back in the 1920s and 30s.

You need 3 basic ingredients for an Italian Beef sandwich.

A soft roll with a nice crunch to the crust. Tender, thin-sliced beef. Juice, or jus, full of classic Italian spices like oregano and garlic, with a dash of red pepper.

Order yours dry, easy dipped, or dipped, depending on how much gravy you like. Top it off with sweet peppers, or another Chicago classic—spicy giardiniera. Request your peppers on the side (in a container), or on the sandwich.

If you’ve saved your appetite for something big, make your sandwich a combo, which means you get an Italian sausage nestled in the beef.

This is a filling meal even if you don’t pair it with a serving of hand-cut fries. Take a walk and then look for a sweet little café where you can relax with an espresso or cup of coffee | Best Coffee.

2. Take Me Out to the Ballgame

The hot dog. A simple little sausage sitting in a bun. The hot dog is simply classic Chicago food.

That said, this Chicago street sandwich is far from simple. You can order a hot dog naked—dog and bun, no condiments, or you can enjoy it as one of the following:

Depression Dog

Start with a hot dog on a steamed bun. Add yellow mustard, a little onion, and a few sport peppers lined up along each side of the dog. A smattering of sweet relish, a serving of fresh-cut fries.

All this is rolled up in paper. The fries soak up a bit of the mustard and onion. So much yum your senses can hardly bear it.

Hot dogs and Chicago go back a long way. During the Great Depression, vendors sold them from street carts on Maxwell Street. They cost a nickel each.

Dragged Through the Garden

This is the quintessential Chicago-style hot dog and it’s monikered as such by hot dog vendors and sandwich shops alike.

Begin with an all-beef hot dog on a steamed poppy seed bun. Add the following toppings in order:

  • Yellow Mustard
  • Neon Green Pickle Relish
  • Chopped Onion
  • Tomato Wedges
  • Dill Pickle Spear
  • Sport Peppers
  • Sprinkle of Celery Salt

Prepare for your taste buds to sing. Of course, you can find all kinds of other hot dog variations in Chicago, but this is the authentic Chicago Dog! Also, notice the absence of ketchup.

3. La Jibarito

Now, we switch gears, and cultures, and taste another Midwestern delicacy, the jibarito (HEE-bar-EET-oh) sandwich. While it’s found primarily in the Chicago-area, this sandwich has island roots.

Created back in the 1980s, by Juan Figueroa, owner of Borinquen, the jibarito employs fried plantains instead of bread. Sitting between the fried plantains, you’ll find your choice of thinly sliced steak, chicken, ham, pork or vegetarian fillings. Garnish is lettuce, tomato, cheese, and mayo.

Hint: For the original, and more authentic jibarito experience, stick with the thinly sliced steak.

We can’t imagine anything better than a robust coffee drink as an après-sandwich treat.

4. Pork Chops and Applesauce

Or is it pork chopsh and apple shauce? You know, there’s an ongoing debate over whether it’s a Humphrey Bogart or Peter Brady line. Either way, if you visit or live in Chicago and haven’t tasted a pork chop sandwich (sans apple sauce), you haven’t lived.

The bone-on-a-bun sandwich goes back to the early 1940s. It doesn’t come with apple sauce, but it does come with the chop bone and a few tasty condiments.

Chicago’s pork chop sandwich features a juicy and tender bone-in pork chop. It’s put in a bun and loaded up with mustard, grilled onions, and hot peppers. One popular Southside sandwich shop has been serving these tasty sandwiches for over 40 years—and the fries are free.

Isn’t that schwell?

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5. It’s All Greek to Me

While not unique to Chicago, the Gyro sandwich (pronounced YEER-os) is nevertheless a Chicago favorite. And, at least one company that makes gyro cones, has its headquarters in Chicago.

Gyros are a Greek specialty sandwich, traditionally made from lamb, beef, or pork. Yes, pork! Most restaurants in the Chicago area make them from lamb or beef, but pork is more Grecian.

Shaved from a cone that cooks on a rotating spit, the meat for this sandwich is wrapped in a pita. Then, it’s dressed with sliced onions and tomato. The crowning glory of the gyro is a dollop of tzatziki sauce on top.

When searching for your gyro, make sure you also find a place where you can sip a hot or iced coffee afterward. It’s like having an after-dinner mint in a mug.

How Many Chicago Sandwiches Have You Tried?

We’ve only shared 5 sandwiches loved by Chicagoans and visitors to the city. You probably have a few of your own favorites too.

Make it a point to try out a few new Chicago sandwiches before the end of the year. It’s always fun to taste test some of the fantastic food offered all over the Chicago area.

If you’re in our part of the city, come on over and enjoy a coffee drink with us. Stay for dinner and we’ll share a few of our favorite sandwiches. We can’t wait to meet you! We welcome guests at our Evanston and Streeterville locations.