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.

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.”