How to do Oktoberfest 2019: A first timer's guide

Blog 8 iconic Chicago foods and where to eat them
Chicago hot dog by Jeremy Keith on Flickr
Date: 5 September 2019

8 iconic Chicago foods and where to eat them


Lake Michigan. The Sears Tower. Al Capone. The White Sox. Chicago is known for a lot of things. But the Windy City is also famous for its unique delicacies. Think deep-dish pizza, loaded hot dogs, and cheesy popcorn.

If you love hearty, carbalicious grub, there’s no danger of you going hungry in Chicago.

Whether you’re a culinary enthusiast or a foodie newbie, look no further than our list of eight iconic Chicago foods you absolutely have to try on your next trip.

1. Deep-dish pizza

A delicious Chicago staple: deep-dish pizza. Photo: © Lou Malnati’s

Let’s start with the most famous: Chicago-style deep-dish pizza.

The anatomy of a true deep-dish pizza starts with a crispy, buttery crust that’s moulded into a high-sided pan. Traditionally, the dough is layered with mountains of mozzarella, sausage, green peppers and onions, and topped with tomato sauce. Yep, the toppings are layered the opposite way to a traditional pizza. But it works. And it’s yum.

Many restaurants claim to serve the best Chicago deep-dish pizza, but Lou Malnati’s is the crown jewel. Its delectable crust sets it apart. Head there for an early lunch or late-night slice to avoid the crowds.

Tip: If you’re a fan of a good pie or two, don’t miss our tips on where to get the best pizza in Rome!

2. Italian beef sandwich

Tuck into a simple but scrumptious Chicago beef sandwich. Photo: © Al’s Beef

This mouth-watering Chicago food icon started out as a cheap way of feeding large Italian wedding parties. It was brought to Chicago by immigrants in the 1930s and has been a staple ever since.

Consisting of thinly-sliced Italian beef piled high on an Italian roll with sweet peppers and mozzarella, it’s heavenly. 

Operating since 1938, Al’s #1 Italian Beef popularised the sandwich and it’s still one of the best places to try it today.

Tip: If you order your sandwich ‘wet’, it’ll be submerged in a pot of a tasty jus and served dripping. It may be messy, but it’s the Chicagoan way.

3. Chicago-style hot dog

Portillo’s Chicago-style hot dog is no ordinary dog… Photo: star5112 – Flickr / CC BY-SA 2.0

This tempting, warming snack was born in the Great Depression, when hot dogs were cheap, filling and easy to come by. However, there’s nothing cheap about the taste. A Chicago dog consists of a tasty beef wiener in a steamed poppy seed bun, topped with yellow mustard, relish, tomato wedges, chopped onions, a gherkin, hot peppers and celery salt.

For a filling dog, be sure to stop by Portillo’s. With both standard and jumbo versions of the Chicago-style hot dog with all the trimmings, there’s plenty to enjoy. Oh, and wash it down with one of their renowned cake shakes. You won’t regret it!

4. The jibarito

Who knew a plantain sandwich could be so yummy? Photo: rosidae – Flickr / CC BY 2.0

Juan ‘Peter’ Figueroa, owner of the now defunct Borinquen restaurant in Humboldt Park, dreamt up the delectable jibarito after reading a newspaper article about sandwiches made with plantain.

Inspired, he flattened and fried green plantains and sandwiched thinly sliced steak, onions and lashings of garlic-flavoured mayonnaise between the two crispy halves. He named his creation ‘the jibarito’.

The sandwich became an overnight sensation and is now a firm favourite on menus across the city.

The place to try this iconic Chicago food is The Jibarito Stop. A former food-truck-turned-restaurant, people queue day and night to chow down on their pork jibaritos. Be warned: they’re delicious but messy!

5. Good ol’ steak

Meat-lovers won’t go hungry in Chicago. Photo: © Colin Pierson / Gene & Georgetti

Chicago is America’s spiritual steak capital, having once packaged most of the country’s beef. Nowadays, it’s known for flavourful rib-eyes and bone-in filets served in elegant chophouses.

If you’re a die-hard carnivore, there’s no better place to satisfy your meaty cravings than Chicago’s oldest steakhouse, Gene & Georgetti. Opened in 1941, it’s still rocking it seven decades later.

The steak, which is wet-aged before being thrown in the broiler, is quite simply out of this world.

The Rib-Eye Steak is a G&G classic, as is their broiled strip loin, which melts in your mouth. Not a fan of beef? Choose the broiled Greek Style Chicken. It’s a taste sensation.

6. Chicken Vesuvio

Chicken Vesuvio is a treat for the taste buds. Photo: © Harry Caray’s

Italians may have been baking chicken with garlic, lemon, white wine and herbs for a long time, but Chicago can take credit for marketing it as Chicken Vesuvio.

The origins of the name are still being debated: Was it because it started at the charming Vesuvio Restaurant on Wacker Drive, or was it meant to commemorate the explosion of the Mount Vesuvius volcano?

We don’t know, but what’s for sure is that this is a must-try food when visiting Chicago, and Italian steakhouse Harry Caray’s serves some of the best in the city.

Made with a half chicken or boneless breast, quartered potatoes, and sweet peas, the powerful flavours will erupt in your mouth. See what we did there?

7. Chicago-style popcorn

Popcorn comes in all different flavours in Chicago

Popcorn is a big deal in Chicago. In fact, it’s such a big deal, it was designated the official snack food of Illinois by the Illinois General Assembly, in 2003.

If you’re after a tasty bite, you can buy every flavour under the sun in Chicago, from almond and macadamia to bacon and pizza. But the most popular with the locals is cheddar cheese and caramel popcorn.

If you’re going to try it, get it from the famous popcorn chain, Garrett. Their patented Garrett Mix is a fine choice, combining sweet Caramel Crisp with savoury Cheesecorn. It should definitely be on your Chicago food bucket list! Oh, and it’s gluten and preservative free. Bonus!

8. To wash your food down: Malört

Not for the faint-hearted: Malört is Chicago’s ‘undrinkable’ drink. Photo: star5112 – Flickr / CC BY-SA 2.0

This may not be a food, but it had to make the list as it’s a rite of passage for any visitor to Chicago over the age of 21.

Jeppson’s Malört is named after Carl Jeppson, a Swedish immigrant who distilled and popularised the drink in Chicago in the 1930’s. Not for the faint of heart, this stuff packs a bitter punch that keeps going for a loooong time.

The key ingredient in Malört is wormwood, a bitter herb known for flavouring absinthe and for its ability to aid various stomach upsets.

Basically, Malört is a liqueur no one likes but everyone loves. It’s actually famous for being undrinkable. If you’re brave enough to try it, head to Inner Town pub, a fun dive bar with a wide range of craft beers and live music. If you want to do as the locals do, order a Chicago Handshake: a pint of Old-Style beer followed by a shot of Malort. Cheers!

Dine with a local expert

If you want to try a load of typical Chicagoan foods in one go, why not book yourself onto a tasty food tour? You’ll likely stop at some of the places we mentioned above and get a real taste of Chicago.

Hungry to go?

Visit the Windy City and try all the tasty foods Chicago has to offer

If our list has got your mouth watering, book your trip to the Windy City and you’ll be chowing down on Chicagoan delicacies in no time. And don’t forget, with Norwegian Reward, you can also earn CashPoints on your hotel and rental car, as well as all your city tours with GetYourGuide.

Find a hotel in Chicago


How to do Oktoberfest 2019: A first timer's guide