10 Must-Try Gourmet Grilled Cheeses in Chicago

By Sarah Freeman | November 6, 2013 By Sarah Freeman  |  November 6, 2013
Photo by: Nick Murway

Is there a more satisfying combination than crunchy bread and melted cheese? We think not, which is why we found ten gourmet grilled cheese sandwiches that are turning the classic upside-down with imported cheese and artisan bread.

  • Bar Pastoral

    The wine bar sister of the artisan bread and cheese shop shows off its goods in a seasonal grilled cheese sandwich. Cow and raw sheep’s cheeses are served with raisin chutney and apples on sourdough bread.

    2947 N. Broadway St.; 773-472-4781

  • Cheesie’s

    With two stores and a truck, this grilled cheese train is not slowing down anytime soon. Its menu includes classics with two types of cheese on Texas toast, as well as the extreme mac 'n' cheese grilled cheese and sandwiches inspired by jalapeño poppers.

    958 W. Belmont Ave.; 773-388-1574

  • The Fat Shallot

    During its first summer on the road, this truck team perfected its signature grilled cheese sandwich. Melty Muenster cheese, caramelized onions and sautéed spinach come sandwiched between crunchy sourdough bread.

    Track the truck via Twitter

  • Little Goat

    This retro diner goes gourmet with its grilled cheese. Two types of cheese - smoked gouda and Mont Amore - are sandwiched with pork guanciale and smoked tomato.

    820 W. Randolph St.; 312-888-3455

  • Michael Jordan’s Steak House

    Good old bacon jam - it's good on just about anything, but is very tasty inside a grilled cheese sandwich made with aged white cheddar and served with a side of tomato soup.

    505 N. Michigan Ave.; 312-321-8823

  • Mity Nice

    This grilled cheese goes by the name of Deluxe. What makes it so over-the-top? The sandwich is stuffed with pimento and sharp cheddar, smoky applewood bacon and fresh watercress.

    835 N. Michigan Ave.; 312-335-4745

  • The Pony

    This Lakeview eatery claims it's home to the original 16-inch grilled cheese (aka, The Clydesdale), made by cutting a Pullman loaf from stem to stern and toasting the oversized slices with melted American and cheddar cheeses. The shareable sandwich is served with a savory tomato-basil dip.

    1638 W. Belmont Ave.; 773-828-5055

  • Rockit Bar & Grill

    Grilled cheese for dessert? It happens in River North, when two slices of sweet cinnamon raisin bread bookend melted brie, apples, baby greens and balsamic hazelnut vinaigrette.

    22 W. Hubbard St.; 312-645-6000

  • South Water Kitchen

    Mr. Grilled Cheese meets Ms. PB&J. This sweet hybrid sandwich combines soft brie with crisp pear and blueberry jam. The special sandwich recently made its debut on the fall menu.

    225 N. Wabash Ave.; (312-236-9300)

  • Terzo Piano

    As part of its menu makeover, the museum-adjacent restaurant added a monthly grilled cheese special. This month it's served with Old Europe brie, candied hazelnut spread and pear butter on New England Pullman bread.

    159 E. Monroe St.; 312-443-8650

Places Mentioned

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Terzo Piano

Italian The Loop
Food22 Decor23 Service20 Cost$58
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Michael Jordan's Steak House Chicago

Steakhouse Magnificent Mile
Food23 Decor22 Service23 Cost$56
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Mity Nice Bar & Grill

American Streeterville
Food22 Decor18 Service22 Cost$26
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South Water Kitchen

American The Loop
Food18 Decor19 Service20 Cost$33
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Rockit Bar & Grill

Bar And Grill River North
Atmo.- Decor- Service- Cost 
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Bar Pastoral

American Lakeview East
Food24 Decor22 Service22 Cost$33

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