Silver Cloud Bar & Grill
1700 N. Damen Ave.
Chicago, IL 60640
This Wicker Park bar and grill is all about retro comfort food, and there's nothing more old school than its scrumptious grilled cheese, just ask the regulars who will easily name this as one of their favorite menu items. While the blend of cheeses is "secret," the grilled cheese is quite traditional, as it's served on Italian bread with a side of old fashioned Campbell's tomato soup, all for only $6.45. Want to kick it up a notch? You can add tomato or bacon for a few more cents.
2218 N. Lincoln Ave.
Chicago, IL 60614
For one of the more unusual grilled cheeses, head to this Lincoln Park joint. While its primary menu item is, you guessed it, burgers, Edzo's also makes a mean inside-out grilled cheese for under $5. What does that even mean? Between the slices of bread, you'll find melted American and Swiss cheese, just like your average sandwich. But the exterior of the sandwich's bread is what makes it really special: Parmesan cheese that's been fried on the griddle. The result? A crunchy, cheesy, amazing sandwich. Edzo's is also located in Evanston.
Spicy Monkey Soup Company
131 N. Clinton St.
Chicago, IL 60661
What goes best with fresh soup, particularly tomato basil, made from scratch? Grilled cheese, of course, and this Loop restaurant will make your cheesy sandwich just about any way you like it. Or, just go with what's on the menu, like the backyard grilled cheese that comes smothered with cheddar and monterey jack, as well as bacon, chicken and barbecue sauce. The grilled cheese offerings are definitely inventive -- like a provolone and mozzarella sandwich paired with blueberry jam -- but give all of the creations a shot, because these are some the best cheesiest options in town.
Related: Best Cheese Curds In Chicago
5260 N. Clark St.
Chicago, IL 60640
Lady Gregory's may be an Irish bar, with plenty of Irish-inspired eats, but it's also all about the comfort food, and that includes an absolutely addicting grilled cheese. That's exactly why they call it the ultimate grilled cheese. Made with a variety of cheeses -- including brie, mozzarella, gruyere and aged cheddar -- in between slices of Parmesan-crusted sourdough slices, it's also unique for its other ingredients: bits of candied bacon and a delightful tomato concasse. And how much is this addicting grilled cheese worth? More than the $10 you'll pay.
Southport Grocery and Cafe
3552 N. Southport Ave.
Chicago, IL 60657
Combine your grocery shopping and gourmet dining experience into one with a stop in the Southport Corridor for a delightful brunch. Before picking up an array of packaged goods, as well as some items made in house by owner/chef Lisa Santos, savor some of the brunch items. While most items on the menu are sweet, Southport Grocery also offers some savory dishes, including a grown-up grilled cheese, known on the menu as a grilled brie. The brie cheese is slathered on pieces of focaccia and perfectly complemented by sauteed mushrooms and spinach, along with a seasonal side, for a reasonable $11.
Related: Best Cheese Shops In Chicago
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