Could there be a food more closely tied to the American coming-of-age story than the grilled cheese? Maybe your relationship with this iconic comfort sandwich started with the tiny pieces your mom would chop it into so your toddler mouth could handle it. As a kid, it became your go-to favorite lunch and mom’s go-to weeknight dinner. Later, it was probably the first thing you learned to cook for yourself, and you labored to find your favorite combination of cheese, bread type, butter amount and burnt-ness. The story even continues now in college, where grilled cheese probably represents the ideal solution to raging drunchies – or just sweet relief, in the form of comfort food, from exam-induced stress.

For these reasons and more, it’s difficult for anyone to be a snob about grilled cheese. It’s a straightforward, universally appealing sandwich that offers a tasty, no-frills meal to invoke feelings of coziness and comfort. But the more you learn about grilled cheese, the more you come to realize that its creation is truly an art form – one filled with nuance and endless possibilities, and one that’s spawned a competitive grilled cheese subculture. It begs the question: What truly makes for the ideal grilled cheese? Is it simply a taste? Is it an emotion? Is it an experience?

To settle the age-old debate, we set out on a cheesy quest through our very own Chicago, home to restaurants with some of the country’s most renowned grilled cheeses.



Famed chef and restaurateur Graham Elliot (who you might recognize as a judge on Master Chef) opened Grahamwich in Chicago’s West Loop as a destination for fresh, inspired and fast meals including sandwiches, truffle oil popcorn and gourmet soft serve. As the ultimate evidence of the much-buzzed-about deliciousness of its food, #grahamwich was soon an established trending topic on Twitter. The grilled cheese in particular rose to glory, soon gracing Food & Wine’s list of top grilled cheeses in America.

This sandwich is as sensational as the reviews make it seem. The bread is grilled to an optimum crispness, is a perfectly even golden brown in color and comes with a powerful buttery flavor for its relatively restrained grease level. Inside is an inventive and seamless medley of Wisconsin cheddar, prosciutto, tomato marmalade and cheese curds, all melted together in a way that seems meticulously engineered to produce the perfect gooeyness (the cheese will inevitable stretch out in long, messy strings in an honestly really satisfying way).

But perhaps the best thing this sandwich has going for it is the presentation: Each meal at Grahamwich comes on a quaint tray complete with a small brownie chunk for palette cleansing, and is eaten either at an intimate 50’s-diner-style counter or a long rustic wooden table shared with others. Not to mention, the entire staff is capped with newsboy hats, for some inexplicable (yet nonetheless charming) reason. The overall effect is that of experiencing a truly gourmet take on all of the classic comfort food favorites in a trendy, quirky and casual setting. The sandwich is more “cool” than “comfort,” but that’s kind of fine by us.

Cheesie’s Pub & Grub:

Cheesie’s, once a humble hole in the wall off the Belmont El stop, has been transformed through recent renovations into a superb grunge-meets-art-deco full out bar, complete with flat-screened TVs lining the walls. It just so happens to also specialize in serving some of the most intensely amazing grilled cheese you can find.

Whether you’ve been bar-hopping and are suddenly hit by the urge to inhale as much grease as humanly possible, or you just want to enjoy an ice cold Mike’s with your grilled cheese (a winning combo), Cheesie’s serves as a great venue for the fulfillment of all your beer-and-cheese dreams. Its laid-back vibe is the perfect atmosphere to indulge in a nap-inducing comfort food meal, and it also lulls you into a sense of calm that might not otherwise exist if you were fully cognizant of what you were consuming. For example, we sampled The Tenderizer, a frightening creation containing cheddar and mozzarella cheeses, fried chicken tenders, bacon, Sweet Baby Ray’s barbecue sauce, Louisiana Hot Sauce, all between two slices of deeply buttered slices of Texas toast and then dipped in ranch. The prevailing feeling after consuming this monster was one of shame and regret, but on a purely taste-level analysis, it was definitely thrilling, despite its similarity to any sandwich that can be purchased from, say, a Sheetz.

The Tenderizer

The Tenderizer

If you’re not feeling up to a side of self-loathing with your grilled cheese, there are tamer yet equally interesting options, including The Caprese, which we also tried. This delicious morsel, served on sourdough, features mozzarella, tomato, olive oil and crushed basil with creamy pesto mayo. It’s a refreshing yet indulgent take on a classic that’s suitable for vegetarian drunchies or a casual lunch. Paired with Cheesie’s perfect crinkly sweet potato fries, you can’t go wrong.


To be fair, it really comes down to what you want in a grilled cheese. What does grilled cheese mean to you? If it means unashamed, possibly drunken indulgence and a mindset so relaxed it borders on grunge-y, head to Cheesie’s. If you prefer a more streamlined, “designer” grilled cheese experience, Grahamwich prevails.

But if we had to make a decision, we’d have to go with Cheesie’s. Not only does it offer more options, which are each individually interesting, but the ambience of the bar and style of the sandwich are much more true to the entire grilled cheese ethos. Welcoming, comforting and delicious almost to a fault – you can’t get much better than that. No tomato soup necessary.