The Run Down

This guide requires you to start with an empty stomach, because you'll be merrily strolling through South Loop and the Near South Side, eating and drinking more than you ever need. It starts at a classic Chicago diner serving deep-dish pizzas, Italian lemonade, and a famous breaded steak sandwich. You'll then make your way to a local brewery for a chocolate cake and beer pairing to finish things off.

1. Steak Sandwich @ Ricobene's

2. Cake and Beer @ Moody Tongue

1. Ricobene’s

We’re kicking things off at Ricobne’s, a family-owned pizza and Italian eatery that’s a staple in this South Side neighborhood. We’re here for one thing:  their breaded steak sandwich, invented by former owners and twin brothers, Frank and Sam Ricobene, in 1976. They credited this single idea as the catalyst that has kept them open ever since.

Ricobene’s is sort of on its own island along 26th street. It’s on a block sandwiched between two highways, the I-90/94 overpass to the west and I-55 to the east. They act as artificial boundaries cutting this block off from everything else, which means the area hasn’t really changed since Ricobene’s setup shot back in 1946.

Now let’s get to eating. We’re getting their breaded steak sandwich. It’s a thin steak that’s breaded, deep-fried, and smothered in peppers, cheese, and a sweet tomato sauce.  While they’ve been serving this sandwich for 40 years, their sandwich created a buzz when it caught national recognition from a food writer a few years ago, claiming it as the best sandwich in the world.

We’ll let you be the judge of that, but it’s a mighty fine sandwich worth traveling a bit further out of your way to try.

Here are some other tips to keep in mind.

– You can order the sandwich in two sizes. Regular or King. The King size is a good option if you want to split between two people.

– They’ll ask if you want peppers and cheese. Say yes.

– Other good options are the Chicken Vesuvio (Breaded chicken breast, garlic butter with onions, lettuce, tomato & Mayo) and Chicken Parm (Meatless Sauce and Parmesan Cheese) sandwiches.

2. Moody Tongue

After a savory meal, it’s only fair to your palette to offer it something refreshing and sweet, which is why we’re going a few blocks away to the Moody Tongue brewery to hang out in their tasting room. It’s located in a quiet corner set off from the main streets around it. Here are a few notes to help plan your visit.

– The taproom is currently open Wednesday – Saturday. See details on hours here.

– Reservations for the bar can be made here.

– They also have a separate Michelin-starred dining room too. We didn’t visit their dining room for this guide.

It’s actually easy to miss. Besides a small decal on one of the windows by the door, there isn’t any other prominent signage nearby. The brewery is housed in a brick building that blends in with everything else nearby, but the oversized entrance and black-painted doors lets you know there’s something different on the other side.

When you walk in, you’ll be greeted by a host who will escort you up a few flights of stairs to their second-floor taproom. At the center of their bar is what looks like a living room straight from the pages of an interior design magazine. A massive skylight in the roof casts comforting rays of natural light into the taproom, giving it a warmth against the backdrop of black paneled walls and black painted brick. Here’s another angle of that same space. Post up on the couches and make yourself at home. Or if you’re sick of your home after being stuck there for a year, there are also regular dining tables and booths.

You’ll find three things on the taproom menu: beer, chocolate cake, and oysters. You may be wondering how this pairing came to be — it comes from the mind of owner and brewmaster Jared Rouben, a trained chef who envisioned a brewery founded on pairing traditional culinary techniques with the art of brewing beer.

You see that come through on his beer menu, filled with interesting beers like Shaved Black Truffle Pilsner, Toasted Rice Lager, and Caramelized Chocolate Churro Porter.

We went full chocolate and ordered this giant slice of 12-layer German chocolate cake and paired it with a flight of three different chocolate-inspired beers.  This cake, which sells for $20, can easily be shared between three people or even four if you want to stretch it.

It’s a decadent dessert with a varying mix of chocolate buttercream and expresso cheesecake in-between each layer. It’s the type of dessert you’ll randomly get a craving for two weeks later. If you need more of this cake in your life, you can find the recipe here.