Where to find the best grilled cheese in Chicago

Photo of a grilled cheese sandwich with tomato soup.

Grilled Cheese from Gayle V’s Best Ever Grilled Cheese. Photo: Monica Eng/Axios

The dreary weather this time of year has us craving a hot and crispy grilled cheese sandwich with soup.

  • So we’re looking for solace in a food fight over the best grilled cheese in town!

Monica’s choice: Ever since I tried this buttery, toasty treat from Gayle V’s Best Ever Grilled Cheese stand at Green City Market, I’ve been in love.

Context: The classic uses local sourdough from Bennison’s Bakery, butterkäse from Prairie Pure, and butter from Nordic Creamery ($7.50).

  • Once sold only at farmers markets, now they’re available for breakfast or lunch at Gayle’s in the basement of Block 37. Yum.
One hand holds half of a grilled cheese while the other half sits on a white plate.
Fat Shallot grilled cheese. Photo: Justin Kaufman/Axios

Justin’s Pick: I am a fan of a grilled cheese at home. (The secret is mayonnaise instead of butter.) But if I have to go out, I’ll order the staple at Fat Shallot.

Context: The food truck-turned-restaurant has locations in Lincoln Park and at Revival Food Hall downtown.

  • The sandwich includes sourdough bread, Muenster cheese with sautéed spinach and caramelized onions ($8.95).
  • Get a side of tomato bisque soup for $5.

As always, our lactose-indulgent readers have plenty of cheesy opinions of their own:

Leslie M.: “The impossibly rich 5-cheese masterpiece at Lady Gregory’s in Andersonville. Gruyere, white Cheddar, mozzarella and brie with fried shallots and bacon confit on Parmesan-crusted sourdough.”

Monica H.: “Chef Debbie’s grilled cheese at the Peckish Pig paired with a home brew will cure your ailments, especially on a dreary winter afternoon.”

Rebecca H.: “Here in McHenry County in Cary and Crystal Lake: Breaking Bread has a grilled balsamic cheese with sweet peppers and balsamic dressing baked right on the sandwich. Yum!”

Maria G.: “The grilled cheese and tomato soup at Four Moon Tavern in Roscoe Village is the perfect match.”

McKinley S.: “Grilled Cheese Recipe: Carver 47 at Kenwood. Don’t skimp on the red pepper jelly they offer, a delicious combination of hot and sweet.”

Diana J.: “Hands down, it’s the CB&J at Hopleaf on North Clark Street: sourdough bread, homemade cashew butter and raclette cheese, deep-fried, with a mound of their fabulous fries (served with aioli for dipping).”

  • “And you can accompany it with a beer from its extensive list of draft beers or a glass (or carafe) of wine.”

Paul F.: “The grilled cheese (and accompanying side of spicy tomato soup) from Spoke & Bird in the South Loop ticks all the boxes.”

Gary D.: “Try the Waitress Special at the Chuck Wagon in downtown Wilmette. Idea!”

Ana R.: “The best grilled cheese is at Everdine’s on Jefferson Avenue in Naperville. Their entire menu consists of different types of grilled cheese!”

round f.: “Best Grilled Cheese: Ten Mile House in Evanston and Lady Gregory in Chicago.”