10 Must-Try Grilled Cheese Sandwiches in Chicago

The best thing since sliced bread is melting cheese between it
August 31, 2017
by Matt Kirouac

Is there a more satisfying combination than crunchy bread and melted cheese? We think not, which is why we found 10 gourmet grilled cheese sandwiches that are updating the classic with imported cheese and artisanal bread.

The Ruin Daily
A contender for cheesiest grilled cheese in town, The Ruin Daily's version features a whopping four cheeses both inside and outside the sandwich. It all starts with sourdough, which gets filled with fontina, Swiss and cheddar. Parmesan goes on the outside of the bread before it’s griddled, lending a salty crunch to the exterior. For those looking to up the ante further, tuna can be added.

328 S. Jefferson St.; 312-929-2707

Little Goat
This retro diner goes gourmet with thick slices of bacon-Gouda bread spread with two types of cheese, cheddar and Gjetost — a dark, sweetish Norwegian goat cheese. It's finished with guanciale and tangy apple-tomato relish. 

820 W. Randolph St.; 312-888-3455

Bittersweet Pastry & Cafe
After almost 25 years, Lakeview’s venerable Bittersweet Pastry & Cafe has updated its lunch menu with a roster of signature sandwiches. This includes two riffs on grilled cheese, one made with ham, fig and Gruyère, and another with fresh tomatoes and both cheddar and Gruyère on Italian bread. All sandwiches feature Bittersweet’s fresh bread. 

1114 W. Belmont Ave.; 773-929-1100

The quality of the food at this Andersonville beer bar never fails to amaze. Case in point: This combination of housemade cashew butter, fig jam and raclette cheese on sourdough bread. It's pan-fried and served with Stilton mac 'n' cheese and potato chips.

5148 N. Clark St.; 773-334-9851

Three Arts Cafe
Everything about Brendan Sodikoff's ritzy cafe inside the five-story Restoration Hardware showroom is upscale — crystal chandeliers, stone fountains and even the grilled cheese, which is made with cheddar and truffle butter on housemade sourdough.

1300 N. Dearborn St.; 312-475-9116

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

Multiple locations 

Michael Jordan’s Steak House

Good old bacon jam. It's great on just about anything but is especially tasty inside a grilled cheese sandwich made with raclette and tomato confit and served with a side of tomato soup.

505 N. Michigan Ave.; 312-321-8823

M Burger
Those who really want to double down on their grilled cheese can head to M Burger and order off the secret menu for something truly extravagant. Order a sandwich here “Roman-style,” and regular buns will be replaced with two grilled cheeses. That means anything from grilled chicken to a burger can be sandwiched between two other sandwiches. 

Multiple locations

Same Day Cafe
This quintessential cafe still serves one of the mightiest grilled cheeses in Chicago. Simple, wholesome and decadent, it’s got cheddar and smoked Gouda on fragrant housemade rosemary bread.

2651 N. Kedzie Ave.; 773-342-7040

South Water Kitchen
Grilled cheese meets PB&J in this sweet hybrid of a sandwich, combining two classic comfort foods into one with creamy Brie, crisp pear and blueberry jam. It’s all slathered on whole grain bread and pan-fried in butter. 

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

grilled cheese
west loop
logan square
river north
gold coast
grilled cheese sandwich
chicago sandwiches