The 8 Best Grilled Cheese Sandwiches In Chicago

By Chuck Sudo in Food on Aug 13, 2014 8:30PM

We're on a comfort food kick lately here at Chicagoist with these best of lists and, to be fair, we didn't think the weather heading into mid-August would be agreeable for grilled cheese. Yet, here we are, enjoying climes more akin to the Pacific northwest heading into the dog days, drooling for a grilled cheese sandwich.

We sat down and put together this list, which we never consider definitive especially after you all weigh in. As always, debate, dissect and discuss.

The Scout
In a battle of sheer size, The Scout’s grilled cheese is a clear winner. Right at the top of the menu, demanding your attention, is The Scout’s Signature Foot Long Grilled Cheese. The sandwiches are made with brioche bread and come with a tomato basil dipping sauce. There are two staple flavors, a standard three cheese and one with bacon and jalapenos, and a featured special that rotates on a regular basis. This sandwich landed The Scout on Zagat’s list of 10 Bars With Killer Food and is absolutely worth a try. — Sophie Day

The Scout is located at 1301 S. Wabash Ave.

Silver Cloud
Specializing in “comfort food,” Silver Cloud’s grilled cheese is just like Mom used to make. A simple sandwich with a cheese blend between two pieces of buttery, crispy bread. It’s even served with Campbell’s classic tomato soup on the side. Add tomato or bacon, if that’s how your mom made hers special. — Michelle Meywes

Silver Cloud is located at 1700 N. Damen Ave.

Old Oak Tap
On paper, there is nothing especially extraordinary about Old Oak Tap’s grilled cheese sandwich, however its execution is what makes it stand out. Wisconsin cheddar, Swiss and sliced tomato are all standard ingredients, but the addition of brie adds a subtle flavor boost and its grilled sourdough bread provides an enjoyable contrast to the otherwise creamy concoction. Traditionalists will enjoy the fact that the Tap served its grilled cheese with a small side of rich, tangy tomato soup for dipping. Add bacon, slaw or a fried egg to your sandwich for additional heartiness and get it with a side of mashed potatoes for added comfort food satisfaction! — Katie Karpowicz

Old Oak Tap is located at 2109 W Chicago Ave.

Diner Grill
The Lakeview trailer, aka "that greasy spoon that sells Lotto tickets,” is open 24 hours, though it really comes alive after midnight, when the drunk crowd shuffles in. (Tamales, which you can regularly find across the street at The Long Room, are decent at soaking up alcohol.) But if you want to keep the party going, head to Diner Grill for an interactive grilled cheese experience. The cooks, wearing old-timey soda fountain hat and apron, are masterful with a spatula. The speed and accuracy at which they take a trolley car’s worth of grilled cheese orders and cook them to perfection is a dying art. Amidst the chaos of the cramped confines, a delicious, toasted, melty grilled cheese is delivered to your little counter space. This will be the best decision you’ve made all night. — Allison Kelley

Diner Grill is located at 1635 W. Irving Park Rd.

Grilled Cheese at Marion Street Cheese Market
When it comes to cheese, few shops in Chicago take as serious and professional an approach as Marion Street Cheese Market in Oak Park. It’s no surprise that their grilled cheese is also a show stopper. The melted sandwich changes seasonally, so keep an eye out for a rotating medley of artisanal cheeses and add-ins. Their current summer grilled cheese features Somerset Cheddar, the quintessential English cheddar, bacon, tomatoes and avocado on Labriola sourdough bread. — Erika Kubick

Marion Street Cheese Market is located at 100 S. Marion St., Oak Park..

Cheesy Focaccia at JP Graziano
JP Graziano is famous for their delicious traditional sub sandwiches, but their mini cheese focaccia are just is good. They toast D'amatos mini tomato focaccia filled with provolone until the tomatoes on the focaccia are slightly crispy and the cheese has turned deliciously gooey. In the winter these are perfect for dipping into JP Graziano’s daily soup selection.— Melissa McEwen

JP Graziano is located at 901 W. Randolph St..

CB&J at Hopleaf
Two childhood food favorites from our past are PB&J and grilled cheese, both classic templates that always end in delicious and sometimes nostalgic results. The old standards of childhood, the timeless creamy with grape jelly or toasted white bread with Kraft singles, hold a special place, but we’ve grown up a bit and so have our sandwiches. When we need a bit of refined comfort between two slices of bread, we head to Hopleaf for their CB&J. Hopleaf has mashed up our two favorite childhood sandwiches into one elevated concoction that uses a much higher quality of ingredients than Mom use to make. A homemade cashew butter and fig jam with just the right amount of sweetness is melted with rich and creamy Morbier cheese between two thick slabs of sourdough bread. The whole gooey beauty is pan fried with lots of melted butter, served warm with a nice toasty crunch encasing the salty and sweet combo inside. It’s served with their stilton mac & cheese and housemade potato chips, but we’d gladly trade in the sides for another sandwich. — Lisa White

Hopleaf is located at 5148 N. Clark St.

Cheesie’s Pub & Grub
Open until 4 a.m. on weekends, Cheesie’s Pub & Grub is a favorite among the late night crowd in Lakeview. The restaurant takes the classic sandwich head on with deliciously greasy creations like the Tenderizer. A fan favorite, the sandwich piles gooey mozzarella and cheddar cheeses on Texas toast with chicken tenders, bacon, barbeque sauce and hot sauce. Those less inclined towards meat may prefer the Mac, a combination of American and merkts cheddar with homemade macaroni and cheese. All of the restaurant’s sandwiches are served with an accompanying dipping sauce that can range from tomato soup to pesto mayo and beyond. I worked in the kitchen at Cheesie's for a year-and-a-half and still I find myself eating there on a monthly basis. If the golden brown sandwiches weren't enough, the $4 bar will surely keep you coming back. — Robert Martin

Cheesie’s Pub & Grub is located at 958 W. Belmont Ave.