April is National Grilled Cheese Month and, lucky for you, there’s plenty of ways to celebrate in the Windy City. That’s because restaurants the whole city over – from pubs to upscale restaurants – often have their own version of a grilled cheese sandwich. In addition to the ones listed here and here, these restaurants all offer a perfectly toasted grilled cheese, and plenty of gooey cheese between two slices of bread.
736 N. Clark St.
Chicago, IL 60654
Best known for its burgers, this casual River North restaurant also offers a great variety in sides, salads and, of course, sandwiches. When it comes to the grilled cheese, it’s made with three cheeses: jack, cheddar, and gruyere. It’s melted to gooey perfection. Pair this $8 sandwich with a Tuscan Tomato soup for just $2 more and you’ve got a match made in heaven.
5347 N. Clark St.
Chicago, IL 60640
Since this Andersonville restaurant is all about southern comfort food, it should come as no surprise that they’ve put a great twist on the traditional grilled cheese sandwich. That’s because they’ve made it with a southern dip: house-made pimento cheese! In fact, they don’t even call it a grilled cheese. Their pimento cheese, only served during lunch, comes on toasted rye bread with chowchow and your pick of one side to go with it, all for $9. If you’re looking for some beef to go with your grilled cheese, they also offer a pimento cheese burger.
BIG and Little’s
860 N. Orleans St.
Chicago, IL 60610
BIG and Little’s Facebook
With so many tacos and other options on the menu, it’s easy to overlook the grilled cheese, but don’t, because it’s worth every penny, no matter which location you go to. Just know this: if you head to the near north side, their grilled cheese is deep fried to perfection. For just $5.50, this deep fried treat is made with either American Swiss or American cheese. If you head up to the Lakeview location, you’ll still get a perfectly crisp sandwich but it won’t be deep fried. This delicious sandwich clocks in at a mere $2.95. (They only accept cash in their near north spot).
Related: Best Breakfast Sandwiches in Chicago
2056 N. Lincoln Park W.
Chicago, IL 60614
There’s so much to choose from at the original Lettuce Entertain You restaurant, so keep it simple and grab the grilled cheese sandwich. The only problem with that is there’s nothing simple about this sandwich. For starters, it’s incredibly cheesy, made as it is with two slices of cheddar and two slices of Swiss. Bacon and tomato can also be added for even more flavor. RJ Grunts has also been known to offer, on occasion, a burger special, which is burger surrounded by a grilled cheese.
1039 N. Western Ave.
Chicago, IL 60622
Get your fill of rustic fare at this West Town neighborhood restaurant. The entire menu is packed with gourmet comfort food, but one of the favorites is easily the grilled cheese, which comes with, just as it should, soup, a tomato fennel one to be precise. The sandwich is made with three cheeses — cheddar, provolone, and Wisconsin raw milk gruyere — perfectly melted, as well as cured tomato, all on sourdough for $10. For an additional $2, you can also add bacon.
Elizabeth SanFilippo is a freelance writer, who enjoys trying new foods from all over the world. But her favorite city for culinary treats will always be Chicago. When not writing about food, she’s working part-time at a culinary vacation company, The International Kitchen, based in the Windy City. Some of her work can be found at Examiner.com.