A Bostonian’s Guide to Chicago Food



By Andy Boyle

(Editor’s note: Andy is from a small town in Nebraska and has spent about a year each in Chicago and Boston. He knows he’s not really from either city so he shouldn’t speak for them, but he can do both city’s accents horribly. So that’s good enough for us.)

As a dude who used to live in Boston but now lives in Chicago, both cities have great food. I know in Boston you’ve got the oldest restaurant in America. But in Chicago you’ve got the oldest man working as an assistant manager at a McDonald’s. So the cities have a lot in common.

This guide is meant for the Bruins fan visiting Chicago sometime during the Stanley Cup finals. I’m qualified to write this guide because I’ve researched eating in both cities by taking extensive Instagram photos of my food. So, enjoy the City of Big Shoulders, Boston pals.  And in the words of my Boston friends, “Hey you wicked pissah, let’s go Sox and Bruins and Pats and that soccer team!”

Deep Dish Pizza– A fact that’s not as well known, but the city’s deep dish pizza was used to rebuild the Loop following the Great Chicago Fire of 1871. Now mainly loved for its nutritional instead of brickmaking qualities, Chicago’s deep dish pizza can be found in most corner stores, gift shops and fast food restaurants. But if you want real deep dish, Harold’s Chicken Shack No. 62 in the South Loop is the place to go. The Harold’s Chicken Shack’s deep dish pizza is known for its famous caramelized crust. Be sure to order it extra deep and they’ll throw a few uncut sausages on the top, just the way ol’ Harry used to make it. Also check out Lou Malnati’s in Elmhurst, which has Chicago’s second best deepy deep pizza pasta (Deepy deep pizza pasta is Chicago slang for deep dish.) Order some deep dish and you’ll feel so Chicagoan you’ll wanna bribe an alderman!

The Loop — One of the greatest restaurant areas in the world, Chicago’s “The Loop” is home to at least six Chipotle’s, six McDonald’s and four Garrett Popcorn Shops. This area derives its name from how the restaurant selections loop every three blocks. You can grab a quick burrito from Qdoba before heading to your opulent hotel on the Malnourished Mile, taking one of the city’s elevated trains, nicknamed “The R” because of how they’re “raised in the air.” Be sure to spend some time enjoying a sip of your Jamba Juice from one of its four locations. Plan a picnic near the city’s famous moveable bridges that span the Chicago River, which are often raised to impede the city’s weekly lootings.

Portillo’s Hot Dogs — Portillo’s Hot Dogs is known for their wacky and zany hot dog options, with a line regularly going around the block. The restaurant is owned by Doug Portillo, who nicknamed his restaurant the “Sausage Superstore and Encased Meat Emporium” in the late 80s during the sausage and encased meat boom. Be sure to bring a book as locals and tourists alike constantly flock to Portillo’s, causing it to take up to an hour to even find the location. Their most famous dish is the Chicago hot dog, which is made with turkey meat, topped with ketchup on a hamburger bun. Be sure to apply extra ketchup, or else a Chicagoan is known to slap the food out of your hand for “ruining a Chicago hot dog” and then steal your iPhone.

Rock and Roll McDonald’s — This restaurant, first made famous in the Led Zeppelin song “What Is and What Should Never Be,” is the birthplace of Chicago’s blues movement. It’s also where Elvis Presley first shook his hips, showing his intense pleasure after enjoying a McDouble. More recently the location is also noteworthy because you can order a hamburger featuring the parts of more than 1,000 different cows. Take that, Heavy Metal Burger King! The location also blasts both rock and roll hits, “Rock Around The Clock” and “Funky Cold Medina.” Lastly, if you don’t order a Big Mac sometime in your life from this restaurant then it’s guaranteed you’ll never make it to Valhalla. (Valhalla is Chicago slang for “the North Shore,” which is like Boston’s North Shore only less fish smells.)

Photo by Andy Boyle. Andy misses Boston but doesn’t miss bars closing at 2 a.m. and public transportation stopping at 12:30 a.m.