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Breakfast Spot · Logan Square · 7 tips and reviews
Serious Eats: Fried in butter until golden, Rewster's Grilled Cheese is crisp without being greasy. But it's the Pave D'affinois, a funky French cheese that turns molten when warmed, that seals the deal.
120 E Delaware Pl (at Four Seasons Hotel Chicago), Chicago, IL
New American Restaurant · Streeterville · 51 tips and reviews
Serious Eats: The Grilled "Cheese n' Ham" is an expensive option at $17, but it's worth it. House made ham is paired with Prairie Breeze cheese and Miche bread, and served with fresh-cut fries.
3581 W Belden Ave (at N Central Park Ave), Chicago, IL
Sandwich Spot · Logan Square · 37 tips and reviews
Serious Eats: Sharp cheddar, mozzerella, and American are used in the grilled cheese, fusing into one gooey sandwich. The apple-ginger cole slaw works well as the crisp and fresh antidote to all that cheese.
860 N Orleans St (btwn W Chestnut St & W Locust St), Chicago, IL
Fast Food Restaurant · Near North Side · 139 tips and reviews
Serious Eats: 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, fried til golden and crispy.
French Restaurant · Near North Side · 39 tips and reviews
Serious Eats: The award for the butteriest, gooiest, and flat out fattiest grilled cheese in town goes to Bistronomic's grilled cheese. The cheese changes daily.
611 N Fairbanks Ct (btwn Ohio St. & Ontario St.), Chicago, IL
American Restaurant · Streeterville · 46 tips and reviews
Serious Eats: The Guinness Grilled Cheese is only available on the "30 Minute Executive Lunch" menu, but you don't need to be one to enjoy short ribs braised in Guinness and loaded with melted cheddar.
2218 N Lincoln Ave (btwn W Webster Ave & W Belden Ave), Chicago, IL
Burger Joint · Lincoln Park · 24 tips and reviews
Serious Eats: "Edzo's takes an ordinary grilled cheese and puts it over the top with a layer of shredded parmesan on the outside of the sandwich, adding a crunchy-chewy coating that adds a shot of tanginess."
Gourmet Store · Streeterville · 82 tips and reviews
Serious Eats: The Classic Grilled Cheese 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. Comes with a bowl of great tomato soup.
5347 N Clark St (btwn W Summerdale Ave & W Balmoral Ave), Chicago, IL
Southern Food Restaurant · Andersonville · 138 tips and reviews
Serious Eats: The Toasted Pimiento Cheese Sandwich is one of the best grilled cheese sandwiches--housemade Sally Lunn bread is loaded with butter and slathered with flavorful pimiento cheese.
Serious Eats: 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.
2056 N Lincoln Park W (at Dickens Ave), Chicago, IL
American Restaurant · Lincoln Park · 101 tips and reviews
Serious Eats: R J Grunts has improved on the classic grilled cheese by simply adding...more cheese. No one can claim this thing is balanced, but that's really not the point.
New American Restaurant · The Loop · 44 tips and reviews
Serious Eats: If you're looking for crunchiest bread of the bunch, the Artisan Grilled Cheese at Lockwood is the one for you. Before it hits the flattop, Parmesan cheese is sprinkled on to create extra crust.
Serious Eats: At Which Wich in Block 37 you can specify every single detail, from the type of bread to the mustard. Just make sure to fill in the circle next to Triple Cheese Please.
New American Restaurant · Ukrainian Village · 100 tips and reviews
Serious Eats: The tomatoes on the grilled cheese are "cured" before between served with Wisconsin cheddar, smoked gouda, and provolone. The roasted flavor helps tie the sandwich with the tomato fennel soup.
3552 N Southport Ave (at W Addison St), Chicago, IL
Breakfast Spot · Lakeview · 90 tips and reviews
Serious Eats: Grilled Brie Sandwich at Southport Grocery is rightfully called "a grown up version of a grilled cheese" with a layer of gooey brie, fresh spinach and a delicious mess of sauteed mushrooms.
Serious Eats: The panini pressed Grilled Cheddar Cheese & Tomato is nothing out of the ordinary: your choice of swiss or cheddar, paired with tomato slices, but sometimes, a simple sandwich like this all you need
Serious Eats: For an indulgent sandwich, get The Popper: bronzed sourdough is stuffed with cheddar, cream cheese, emerald shards of jalapenos, and crisp slivers of bacon. Served with a side of chipotle mayo.