Grilled Three Cheese at 25 Degrees
The picture kind of says it all. The well executed Grilled Three Cheese ($8) features Monterey Jack, cheddar, and emmi gruyere, and it's a good choice if you find yourself at 25 Degrees feeling a little burgered out. Plus it comes with a sharp arugula salad, too.
Rewster's Grilled Cheese at Rewster's Cafe
In general, the best grilled cheese sandwiches we sampled avoided dressing the sandwich up with every conceivable topping known to man, and instead focused on good bread and melty cheese. Crowning the best seems a little wrong, but it's hard to think of a more flawless example of keeping it simple than the Rewster's Grilled Cheese ($10.00) at Rewster's Cafe. Fried in butter until golden, the bread is crisp without being greasy. But it's the Pave D'affinois, a funky French cheese that turns molten when warmed, that sealed the deal.
Grilled "Cheese n' Ham" at Allium
The Grilled "Cheese n' Ham" ($17) is the most expensive option we found, but it's worth it. House made ham is paired with Prairie Breeze cheese and Miche bread, and served with fresh-cut fries and balsamic ketchup.
Grilled Cheese at Grahamwich
Between the hunks of chewy cheese curds and the buttery crisp on the sliced pullman loaf, the Grilled Cheese Sandwich ($7) from Grahamwich sits solidly on the indulgent end of the grilled cheese spectrum. I have never understood sliced tomatoes on a grilled cheese—I mean if you're going to go all out and eat a meal comprised of cheese, bread, and butter, why ruin it with some wet tomato slices? But in this case, the tomato relish provides a bright sweetness that regular slices of tomato just can't accomplish. Read more here >>
Grilled Cheese at The Brown Sack
Nothing on The Brown Sack's menu is about reinventing the wheel, and that's especially true of the grilled cheese. Sure, three cheeses (sharp cheddar, mozzerella, and American) are used, but by the time they are warmed up in the kitchen, they fuse into one gooey whole. Though all of the side dishes are good, the restaurant's apple-ginger cole slaw works well as the crisp and fresh antidote to all that cheese and butter.
Grilled Ploughman at Pastoral Artisan Cheese, Bread & Wine
With an excellent cheese program and some wonderful crusty bread, we expected greatness from Pastoral. We were not disappointed, but just don't look for the grilled cheese on the menu. Each day, two paninis are available, and one of those is usually what you're after. On the day we stopped by, it was called the Grilled Ploughman, and it included paper thin slices of green apple and a nose-clearing spread of mustard.
Deep Fried Grilled Cheese at Big & Littles
Only the evil geniuses at Big & Little's could have come up with the Deep Fried Grilled Cheese. At first glance, it looks much like a hole-less doughnut. But it's actually a sesame seed hamburger bun with American cheese and bacon slices, which has been dipped in the same batter used to fry soft shell crabs. It emerges from the fryer golden and completely crispy. Amazing.
Big & Littles, 860 North Orleans Street, Chicago, IL 60610 (map); 312-943-0000
Grilled Cheese Sandwich at Bistronomic ($10)
And the award for the butteriest, gooiest, and flat out fattiest grilled cheese in town goes to Bistronomic's grilled cheese. The cheese changes daily, but on our last visit brie was melted between buttery brioche. It's almost too much. Luckily, the sandwich is paired with an acidic salad, which seems to balance it all out.
Guinness Cheddar Grilled Cheese at Markethouse
This one is only available on Markethouse's "30 Minute Executive Lunch" menu, but you don't actually need to be one of those to enjoy the Guinness Cheddar Grilled Cheese. Short ribs are braised with Guinness and then loaded onto bread with melted cheddar. When paired with tomato soup, it's a match made in heaven.
Inside-Out Grilled Cheese from Edzo's
The Inside-Out Grilled Cheese Sandwich ($4.19) at Edzo's starts off as an ordinary grilled cheese made from two pieces of white bread that are filled with American and Swiss cheese. But what puts it over the top is the layer of shredded parmesan that goes on the outside of the sandwich as it cooks on the part of the griddle ordinarily used to toast hamburger buns. The cheese in between the slices of bread transforms into a gooey layer of melted goodness, while the cheese on the outside turns into something resembling a parmesan tuile that adds a shot of tanginess and gives the sandwich some extra chew. Read more here >>
Classic Grilled Cheese at Fox & Obel
It's called the classic grilled cheese ($6.50) for a reason. This version from the airy Fox & Obel Cafe in Streeterville features just the right amount of cheese and no more. The bread is crisp, but not enough to get in the way of each bite. Of course, it helps that the sandwich comes with a great bowl of tomato soup.
Toasted Pimiento Cheese Sandwich at Big Jones
At Big Jones, the outstanding Southern restaurant in Andersonville, chef Paul Fehribach's Toasted Pimiento Cheese Sandwich ($8) is one of the best grilled cheese sandwiches I've ever had. The housemade Sally Lunn bread is a yeasty treat that is absolutely loaded with butter and eggs. The thick slices of griddled bread have an almost crunchy exterior with a crumbly, cornbread-like interior. The bread is so flavorful that most cheeses would get lost in between the slices, but the housemade pimiento cheese at Big Jones is no ordinary dairy product. Read more here >>
Grilled Cheese & Tomato Soup at Old Town Social
As far as side dishes go, pairing grilled cheese with fries or chips makes no sense. Then there is nothing in your meal to break up the unrelenting crunch. But grilled cheese and tomato soup? That's a pair that should stick together. Of the many duos encountered, Old Town Social's grilled cheese & tomato soup ($9.00) sticks out as the one where the two elements depend on each other the most. The bread on the grilled cheese is too thick; the tomato soup is too tart and acidic. But rip off a piece of the sandwich and dunk it in the soup, and everything is right with the world.
Grilled Cheese at RJ Grunts
Remember when you were a kid, and grilled cheese was perfect? All one needed was bread, cheese, and perhaps some butter to create the worlds most earth-shatteringly divine grilled sandwich known to man (or maybe my mom's grilled cheese really was that good). All other embellishments only detracted from the experience. In fact, the only possible way to improve upon grilled cheese was to add more cheese. Well, that's basically what R J Grunts has done with its grilled cheese ($6.50). No one can claim this thing is balanced, but that's really not the point.
Artisan Grilled Cheese at Lockwood
If you're looking for crunchiest bread of the bunch, the Artisan Grilled Cheese ($13) at Lockwood is the one for you. Before it hits the flattop, Parmesan cheese is sprinkled on to create extra crust. But this all serves a purpose, as tthe sourdough is the ideal vehicle for the four cheeses (Shepherd's Hope, Prairie Breeze, Great Lakes Brie, Capriole).
Triple Cheese Please at Which Wich
Particular about your grilled cheese? At Which Wich in Block 37 you can specify every single detail, from the type of bread to the mustard. Just make sure to pick up the right brown paper bag before you make your order (don't worry, our first time was a little confusing, too) and make sure to fill in the circle next to Triple Cheese Please. We went with American, cheddar, and provolone, but there are nine other cheeses to choose from.
The Appleton at Melt
One bite of The Appleton ($7.95) will quell any cynicism as to Melt's sandwich destination worthiness. The Appleton boasts a cheesy melange of Cajun-spiced cheddar, pepper jack, and muenster, topped with red apple slices and bacon aioli, all pressed between a semi-sweet baguette. The sweet apple slices are a nice balance to the medley of part savory/part spicy cheeses that ooze out from the bread with every bite. Read more here >>
Grilled Cheese and Tomato Fennel Soup at Bite Cafe
Tossing a raw tomato on a grilled cheese almost never works. Bite Cafe knows this. That's why the tomatoes on its grilled cheese ($8.00) are "cured" before between served with Wisconsin cheddar, smoked gouda, and provolone. The roasted flavor melds better with the gooey cheese, and also helps tie the sandwich with the tomato fennel soup.
Grilled Brie Sandwich at Southport Grocery
This beautiful sandwich from Southport Grocery starts with a nice layer of gooey brie, but is elevated by other elements that add some serious flavor to go with the creamy cheese. Inside the sandwich is fresh spinach and a delicious mess of mushrooms that are sautéed with salt, pepper, and rosemary. All of that goes between crisp griddled slices of olive oil and sea salt focaccia from Red Hen Bread, completing what the restaurant rightfully calls "a grown up version of a grilled cheese." Read more here >>
Grilled Cheddar Cheese and Tomato Sandwich at Township
The panini pressed Grilled Cheddar Cheese and Tomato ($6.00) at Township is nothing out of the ordinary: your choice of swiss or cheddar, paired with tomato slices. This might not be the grilled cheese of your dreams, but sometimes, a simple sandwich like this--with its ego in check--is all you need to fulfill your basest desires. Read more here >>
The Popper at Cheesie's Pub & Grub
The Popper ($6.95) at Cheesie's Pub & Grub features sturdy sourdough with a perfect bronzing on top. It's stuffed with cheddar, cream cheese, emerald shards of jalapenos, and crisp slivers of bacon. Served with a chipotle aioli on the side for dipping, the sandwich is clearly an indulgence. Read more here >>