15 Ooey Gooey Grilled Cheese Must Haves in Chicago

grilled cheese in frying pan

anjuli_ayer / Flickr / Creative Commons

Grilled Cheese has come a long way since I was flipping them in a pan, or even worse, a microwave in my younger years. The big question may be, is grilled cheese really grilled cheese once you add vegetables and meat to it? The answer to that is yes, yes it is. The basic principles are still there– quality cheese and amazing bread. There are many establishments around Chicago that have embraced this artisan style or even just perfected the classic recipe.
Go out and seek this cheesy goodness.

Chicago’s Best Grilled Cheese Sandwiches:

The Scout

Near Southside
Website

Scout’s foot long grilled cheese with tomato dipping sauce is what first hooked me onto the artisan grilled cheeses. I indulged in the Short Rib Grilled Cheese with a pepper mix and and it was nothing short of phenomenal. They also have a straight triple cheese one, as well as one with bacon and jalapenos.

scout grilled cheese sandwich in chicago

Ross M Perkins / Creative Commons

Northdown Cafe and Taproom

Lakeview
Website

Northdown Cafe take the classic route with grilled cheese. The bread is crispy, yet remains soft, while the cheese is mushy while still being firm as it should be– not runny as some are. The real kicker is the pre-griddle beer dip that compliments the sourdough bread perfectly.

Bar Pastoral

Lakeview
Website

Bar Pastoral gives some artisan flare to grilled cheese by creating it from Prairie Breeze Cheddar, Fromager D’Affinois, Single-Varietal Honey, San Marzano Tomato and serving it with a Fresno Chili Soup. Fancy cheese galore.

Gayle’s Best Ever Grilled Cheese

Various Locations
Website

You’ll have to track Gayle’s down, but you can typically find her and her grilled cheese at Green city market, and many farmers markets throughout the city. There are no foot long sandwiches here, just your typical size– but this is a perfect example for the quality over quantity argument. Her panini press grilled cheeses are out of this world. The best part, Gayle’s uses local ingredients– Bennison’s Bakery bread from Evanston and Butterkase cheese from Prairie Pure Farm in Belvidere.

The Big Cheese On Lincoln

North Center
Website

The Big Cheese serves up their grilled cheese on good ‘ole fashion Texas Toast– which alone makes it quite delightful. Go for the tomato soup to dip it in, or if you are feeling a little out there– order up a Bloody Mary to dip it in.
Oh yeah, don’t forget to get a side of fried pickles as well.

The Big Cheese grilled cheese and tomato soup in chicago

Photo courtesy of The Big Cheese / Kim Epsky Photography

The Fat Shallot

Various Locations
Website

The Fat Shallot– you may need to chase this food truck down the street, but it’ll be worth it. Order up your grilled cheese and they’ll hand it to you in the form of toasty sourdough, muenster cheese with caramelized onion and sautéed spinach mixed in there. To make it even better, opt for the bacon and avocado addition.

Toasty Cheese

Various Locations
Website

Toasty Cheese makes rare appearance in the city, but they do frequent the Truckin’ Around – Food Truck Extravaganza at the Schaumburg Boomers stadium. Being that they specialize in cheese, they have over 10 sandwiches on their menu that do the grilled cheese justice. Seek. Them. Out.

Bar on Buena

Uptown
Website

Bar on Buena doesn’t only have a great beer selection– their grilled cheese is something to indulge in as well. Their Hook’s cheddar & smoked gouda, butter grilled brioche is definitely what you need to order. Do yourself a favor and spend the extra couple bucks to add avocado.

Hopleaf

Uptown / Ravenswood
Website

Hopleaf’s grilled cheese is actually a lot more than just a cheese sandwich. It may be more closely related to a peanut butter and jelly, but trust me on this one. It is called the CB&J. That translates to cashew butter, fig jam and cheese on pan-fried sourdough bread. Intrigued? You should be.

Jerry’s Sandwiches

Multiple Locations – West Town & Andersonville
Website

Jerry’s has 6 grilled cheese sandwiches to choose from– standard to artisan. Each sandwich comes with 2 sides and you can add lettuce, tomato and red onion if desired. Their side choices are quite extensive, so it’ll easy make a satisfying meal. These are no ordinary sandwiches either.

The Sedgewick Stop

Lincoln Park
Website

The Sedgewick Stop may as well be called The Grilled Cheese Stop. The classic design is embraced in the form of  their The Adult Grilled Cheese. Cheddar, swiss and mozzarella are squeezed in between Italian bread with the option to add prosciutto or bacon.

Cheesies

Various Locations– Lakeview / Evanston / Truck / (soon to Wicker Park)
Website

Cheesies embraces their name and it especially shows with their grilled cheese selection. You’ll find 10 crafted cheese sandwiches on their menu with various dipping sauces. Classic offerings, as well as veggie and/or meat loaded options are plentiful.

Grilled Cheese Burgers:

Square Bar & Grill

Avondale
Website

Square Bar & Grill imagines the American Dream to be ooey gooey and cheesy. That is why their American Dream Burger is comprised of a char-grilled burger topped with sauteed mushrooms, apple-wood smoked bacon, and Swiss cheese packed between a pair of grilled cheese sandwiches. And people wondered why I was seeking out the best grilled cheese in Chicago– I would have never known something like this existed!

M Burger

Various Locations– River East / Near North Side / Streeterville
Website

This may be surprise to people since M Burger doesn’t list a grilled cheese burger– but allow me to fill you in on a secret menu item. It is called the Roman Style and it is M Burger’s phenomenal burger patty fitted in between 2 grilled cheese sandwiches. Next time you stop in, definitely try the Roman Style out.

Roman Style grilled cheese burger at M Burger in Chicago

Photo courtesy of M Burger

Herm’s Palace

Skokie
Website

Herm’s Palace is include incase you find yourself way north of Chicago and just absolutely need a grilled cheese.. or a burger. No longer must your compromise. Herm’s grilled cheese burger does away with buns and instead uses a grilled cheese sandwich as the bottom bun, and you guessed it, the top bun as well. Holy moly.

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Ross Perkins

Ross Perkins is the Executive Editor & a connoisseur of all things enjoyable– at least in his mind. He is an avid traveler in the name of inspiring sights, music, food & cars. He is a published photographer & writer that is looking for any reason to get out and explore his surroundings.

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