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Eat Your Way Through a Day in Chicago

VO: Rebecca Brayton WRITTEN BY: Michael Wynands
Windy City? More like tasty! Welcome to MojoTravels, and in this food video, we’re going to lead you through a perfect day of eating in Chicago, focusing on the iconic dishes and culinary treats that you can’t miss when visiting or passing through.

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Eat Your Way Through a Day in Chicago

Windy? More like tasty! Welcome to MojoTravels, and in this video, we’re going to lead you through a perfect day of eating in Chicago, focusing on the iconic dishes and culinary treats that you can’t miss when visiting or passing through.

Breakfast might be the most important meal of the day, but when you’ve got a busy schedule of heavy eating ahead of you, sometimes it’s best to keep it light. That being said, light doesn’t mean grabbing a banana or stale croissant from the continental breakfast buffet at your hotel. Ann Sather is an institution, famous for its ooey-gooey cinnamon rolls. The original location is on Belmont, but all three locations turn out top notch food. Trust us, a cinnamon roll and a coffee is the perfect way to start your eating tour of Chicago.

Consider yourself warned, with only one day in Chicago, we’re going to be going hard with some rather heavy food. Chicago has put their own unique stamp on a number of must-try dishes and none of them are what we could call “light fare”. So buckle up (or rather ditch the belt buckle) as we dive in and eat like hobbits. First up? An early lunch in the form of a Italian beef sandwich.

Most people have eaten their fair share of roast beef sandwiches over the years, but you haven’t lived until you’ve tried Chicago’s unique spin on the dish. The best “Italian beef” in the city is a decades-long debate, but serving them up since 1938, Al’s Italian Beef claims to be the original. The sandwich is characterized by super-thin slices of its namesake meat, served in its own juices on a thick Italian roll. At Al’s, most locals take theirs dipped or “wet”, meaning that the whole thing gets dunked in the jus. Now that’s one tasty treat, available at various locations, including the original one on Taylor Street.

Though Al’s might be the city’s most famous, it’s far from the only spot to score a delicious sandwich. Another great place to try is Johnnie’s Beef, which has been serving up some serious competition since 1961 in the Elmwood Park area. There’s often a lineup out the door at this modest-looking joint, but trust us, their sandwiches are more than worth the wait; the toppings here are particularly well-balanced. In a blind taste test, the right honorable Alton Brown actually judged Johnnie’s superior to Al’s. And so the debate continues!

Depending on where you are in the city, you could also hit up the highly regarded Mr. Beef on Orleans. Sadly, one of the greatest spots for Italian beef, Joe Boston’s, closed shop in 2017 after 70 years of business. RIP Joe Boston’s, a good sandwich gone too soon!

For something totally different, but nonetheless iconic (and of the meaty variety), we highly recommend Manny’s Cafeteria & Delicatessen. Open since 1942, Manny’s has perfected the art of corned beef and pastrami. Everyone from presidents and gangsters have eaten here. Rich in history — and flavor — this is the perfect place to get a pastrami sammy.

Next up on our edible odyssey (consider it second lunch) is one of Chicago’s most famous and contentious dishes… pizza! Now, the pies coming out of Chicago have long inspired debate, both around the world as well as locally. Across America and beyond, people argue whether the city’s unique deep dish pizza is real pizza or not. Locally however, the debate goes even deeper with the question “is deep dish even the pizza we should be known for?”

You see, while Chicago is synonymous with “deep dish”, locally that particular preparation style is often thought of more as tourist fare and a novelty for special occasions. Chicago pizza lovers in the know will tell you that thin crust, tavern-style pies are actually the way to go. To eat pizza like a local, we recommend you head over to Vito & Nick’s, first founded in 1923 and slingin’ pies since 1946. Thin, crispy crust is loaded with toppings and then cut into square pieces for a distinct crispy deliciousness that, unbeknownst to most travelers, is arguably more quintessentially Chicago than most deep dish pizzas.

Okay, so while we think it’s important to acknowledge the secret true history of pizza in Chicago, the fact remains that while you’re in the city, whether it’s touristy or not, you should totally try a deep dish pie. While it might not be a conventional take on the pizza, it is a unique culinary treat that everyone should taste at least once - and taste in the city that does it best. Of all the joints serving it up, Pequod's is arguably the most famous. The outer edge of the pizza is a caramelized halo of goodness, the dough is light and fluffy, the sauce is fresh and bright in flavor, and the cheese is a deliciously gooey mess.

Though Pequod’s might be the most recognizable name in deep dish, it’s far from being the only one. A long-standing favorite is Uno Pizzeria, which has since expanded into a major franchise. While not all Uno pizzas across America are created equal, those coming out of the two locations in Chicago never disappoint. Uno claims to have invented the deep dish; and unlike at Pequod’s, you’ll find little caramelization here; instead it’s a uniform golden brown crust. Of course, there’s no shortage of deep dish alternatives, including Giordano’s, Lou Malnati’s, Pizano’s and Gino’s East, among others.

After a long sit-down pizza lunch, you’ll want to walk around a bit to to shake of the somnambulant effects of consuming a deep dish. With a belly full of cheese and dough, you may find yourself in need to a little pick me up in the form of something refreshing. You could use this time to try another iconic Chicago dish, the famous “rainbow cone” at the aptly named Original Rainbow Cone on South Western Avenue. This shop is only open seasonally, but something tells us you wouldn’t want to walk around with ice cream in winter anyways. (But hey, we won’t judge.) Open since 1926, this landmark serves up a cone loaded with chocolate, strawberry, and pistachio ice cream, topped off with orange sherbert. It’s an odd concoction, but people love it!

We hope that after a few hours exploring the city you’re hungry again, because it’s time for dinner . . . and it’s going to be a doozy. Though perhaps not as iconic as their pizza or beef sandwiches, BBQ is actually one of Chicago’s fortes. Their barbecue scene is arguably among the country’s best, but due to the city’s northern location on the map, it doesn’t always get the love or recognition it deserves. We’re here to help fix that. One of the best options in the city is Twin Anchors Restaurant & Tavern in Old Town. The order? A rack of the mouth-watering baby-back ribs they’ve been serving since 1932.

Over on North Pulaski Road you’ll find arguably the city’s most beloved BBQ joint, Smoque. It might not be an institution like our previous recommendation, but since opening in 2006, it has quickly earned critical acclaim, and legions of loyal customers, both locally, and across the country. Brisket, pulled pork, chicken, sausage, ribs, sandwiches and classic BBQ sides, they do it all, and they do it all incredibly well. In 2019, they, ironically, suffered through a fire, but thankfully they were able to bounce back and reopen.

Last but by no means not least is Lem’s Bar-B-Q on the south side of the city. Located on East 75th Street, Lem’s claim to fame is their dry-rubbed ribs, beautifully smoked to perfection. Of course, Lem’s has more than one dish to offer bbq aficionados. People love the hot links, chicken and rib tips - a Chicago speciality that many argue Lem’s does better than anybody else. Unpretentious, open late and without equal in its deliciousness, Lem’s is proof that Chicago knows BBQ.

Alright, after getting your hands messy eating some delicious Chicago style barbecue, you’re probably feeling pretty full. So go hit the town for a while, walk around, experience the city’s vibrant nightlife and maybe even try that infamous “acquired taste” Chicago liquor, Malört. And after an evening spent hitting the town, we figure you’ll be ready for a late night snack, meaning that it’s time for the last iconic Chicago dish of the day - a hot dog. Our first option is Superdawg in Gladstone Park. Open since 1948, this drive-in is a go-to for late night eats, Superdawg boasts that the beef hot dog on a poppy seed bun it serves is unlike any other. As their menu puts it, “Not a wiener - not a frankfurter - not a red hot - but our exclusive... Superdawg”.

Like with all of its most beloved dishes, Chicago loves to argue hot dogs. Though Superdawg is a cherished institution, it’s not without competition. Portillo’s is another beloved joint with legions of dedicated customers. It’s been around in one shape or form since 1963, and serves up a classic Chicago style hot dog to contend with the best of them. Its success and subsequent franchising (like many of these Chicago restaurant landmarks) means that it feels a bit touristy these days, but there’s no arguing against the quality of its dogs.

Honestly, there are dozens upon dozens of places to try a great Chicago style hot dog, and Chicagoans defend their favorites as the best ones. Gene & Jude’s, Jimmy’s Red Hots, Phil’s Last Stand . . they’re all great. For a truly unique experience however, we chose to go with The Wiener’s Circle in Lincoln Park. Here, the employees hurl insults and profanities at their late night customers, who respond in kind; it’s part of the rough, iconic charm of the place, and its claim to fame. Should you be selected to suffer a verbal tirade, consider it an honor. But the Weiner’s Circle is more than a gimmick, they serve up some truly excellent dogs.

But with only one day in Chicago, there are only so many places you can visit, and only so much you can eat, so we know we’ve left off a ton of great places. But we shall return!


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