5 Sandwiches In Chicago I Can Never Stop Thinking About

A sandwich is the best way to deliver an entire meal between two pieces of bread and Chicago's got no shortage of them. Sure, our city is known for some legendary ones (hint hint, Italian beef); but the truth is, Chicagoans can't live upon a good old beef sandwich alone. As a lifelong Chicagoan, I've eaten a ton of sandwiches. There are so many I've loved along the way that I've lost count. But at any given time, my brain cycles through a chosen few and if you put any of them in front of me I would be absolutely ecstatic.

These are merely five I've had (the original list was much longer) that have stood out in my memory. As time goes by and I continue to try new ones, I'm sure I'll find another sandwich that'll eventually end up somewhere on here. That's just the joy of living in a big city: the plethora of shifting choices. Whether you're from Chicago or you're coming in for a visit (please do!), who knows, one of these sandwiches just might become one of your favorites too.

If you were going to ask me the completely torturous question of "Hey, Dennis, what's your favorite sandwich in Chicago?" the Pork and Greens sandwich from JT's Genuine Sandwich Shop in the Irving Park neighborhood might actually be my final answer. It involves a light and crisp sesame seed roll filled with thinly shaved pork tenderloin, melted provolone, grilled rapini, Calabrian chili aioli, and dressed with a bit of the cooking jus from the meat. 

If that sandwich sounds suspiciously similar to Philadelphia's roast pork sandwich (which has a similar build sans the Calabrian aioli) that's because this is JT's Genuine's nod to it. Even though the pork in this sandwich is lean, it's sliced so thinly that it practically melts as you chew. The rapini (otherwise known as broccoli rabe) adds a lightly vegetal bitterness to balance out the nuttiness from the cheese and the meaty backdrop of the pork while the aioli brings an extra layer of fat. For those of you vegetarians who feel left out, there's a Beans and Greens melt which replaces the pork with beans (but uses different bread) so you can join in on the fun, too.

TriBecca's Sandwich Shop, located in Avondale, sells a cauliflower sandwich called the Frosted Cauliflower that treats the veggie in a way that may appear familiar to you. That's because this thing includes a thick cross section of cauliflower that's dredged in panko and deep fried before being topped with cheddar, tarragon-mustard aioli, and shredded lettuce all layered in a butter-griddled bun.

Yep, upon first glance, this thing looks exactly like a classic fried fish sandwich. It comes across as a good sturdy meal, not an obligatory vegetarian menu item. Sure, vegan fish substitutes do exist, but honestly that's not the point here. The cauliflower is juicy, reminding you that you are indeed enjoying your vegetables (okay, even if they're deep fried), but in a really fun and playful way. Meat lovers can still enjoy plenty of other options, like TriBecca's unique version of a Cubano sandwich which is made almost entirely with local ingredients. But try the Frosted Cauliflower just once and you might start skipping the meat altogether.

Chicken Caesar wraps have a habit of going viral online now and then, and I'm guilty of enjoying one from time to time. Sure, they're simple. A chicken Caesar wrap is basically the namesake Caesar salad wrapped up in a soft flour tortilla. But Moonwalker Cafe, in the tiny neighborhood of Belmont Gardens, has one that's so minimal I'm constantly surprised I love it. It's romaine lettuce and grilled chicken tossed in a house made Caesar dressing then rolled up in a spinach tortilla. There's no additional shaved parmesan nor are there any croutons or crispy bits of anything to give it some extra crunch.

What you're left with are the bare essentials, which means this thing is simply refreshing. You can't use that term to describe most sandwiches (we can argue whether or not a wrap is a sandwich another day), which makes the Chicken Caesar Wrap from Moonwalker an outlier on this list. The dressing is light and savory, and once you're done eating it, chances are you'll find yourself planning on getting another one next week.

Hermosa Restaurant is named after the Chicago neighborhood it resides in, which is, well, Hermosa. This tiny shop once started out as an easygoing hot dog and sandwich stand servicing the good folks of the neighborhood. Years ago when I first visited, I noticed a section of the menu featuring Asian-inspired sandwiches that more than intrigued me. I dove in, started eating, and never came up for air. The offerings changed throughout the years, but once chef and owner Ethan Lim added a Cambodian fried chicken sandwich to the menu (to honor his heritage), it became a hit and never left. 

The sandwich features a fried chicken thigh that's been marinated in a spice blend known as kroeung which contains ingredients like lemongrass and garlic. It's topped with a bright papaya salad and a rich garlic mayo. You can order it online during the day, but at night the tiny kitchen transforms into a fine dining space that you need to reserve months in advance. During those experiences, Lim serves high-end, coursed-out Cambodian food — which makes sense, as he's previously worked in Michelin-starred kitchens like Next here in the city.

Notice I didn't mention Italian beef on this list, not even once. That's because I'm almost always within a stone's throw of one (though for the record, I love both Johnnie's and Al's Beef on Taylor). My last pick is one of the sandwiches we Chicagoans also consider a classic; though from an outside perspective, it might seem like a somewhat bizarre choice. That's because it's a pork chop sandwich topped with loads of grilled onions and yellow mustard tucked inside a cheap white bun, and that's it. Simple enough, right? Not so fast. The pork chop sandwich at Jim's Original near the University of Illinois Chicago campus comes with a bit of a catch — it has a bone in it.

That means there's a trick to eating this thing. Before you take your first bite, you have to locate the bone and pinch it with your fingers so you know exactly where it is. Then you eat the sandwich up until you've reached the borders of your personal safety measure, and you're good to go. Jim's is arguably more famous for being the originator of the Maxwell Street Polish, which is sort of like the Chicago-style hot dog's long-lost sibling, so you can also pick up one of those while you're there for a visit. Just a fair warning: The place is literally just a walk-up window. There are counters built into the exterior of the building where you can scarf down your food, then enjoy the rest of your day.