Food & Drink

Grill ‘Em All: Discovering Chicago’s 16 Melty Masterpieces!

Grilled cheese is a comfort food that brings back memories of childhood. This simple sandwich, made with bread and cheese, has become a staple in American cuisine.

Chicago is home to some of the best grilled cheese sandwiches in the country. From classic renditions to innovative twists, there is something for everyone.

The key to a great grilled cheese sandwich is the bread and cheese. The bread should be crispy on the outside and soft on the inside, while the cheese should be gooey and melted.

The combination of the two is what makes the sandwich so irresistible. Some of the best grilled cheese sandwiches in Chicago use artisanal bread and locally sourced cheese to create a unique and delicious experience.

Chicago is also known for its diverse food scene, which is reflected in the grilled cheese sandwiches.

Some restaurants have taken the classic grilled cheese sandwich and added their own twist by adding ingredients like bacon, avocado, and even macaroni and cheese. These innovative sandwiches are not only delicious but also an adventure for your taste buds.

Whether you are a grilled cheese purist or an adventurous eater, Chicago has something for you.

Join me as we explore the best places for grilled cheese in Chicago.

1. Au Cheval

Au Cheval
800 W Randolph St, Chicago, IL 60607 (Google Maps)

Au Cheval is a must-visit spot for grilled cheese lovers. This upscale American diner offers a unique take on the classic dish.

The cheese is perfectly melted and paired with a house-made Dijonnaise sauce that elevates the flavor.

The dimly lit ambiance adds to the cozy atmosphere. The staff is friendly and attentive, making the dining experience even better.

Be prepared for a wait, but it's definitely worth it. Au Cheval is a great spot for a delicious grilled cheese sandwich.

2. Wildberry Pancakes & Cafe

Wildberry Pancakes & Cafe
130 E Randolph St, Chicago, IL 60601 (Google Maps)

Wildberry Pancakes & Cafe is a breakfast and lunch spot that serves up more than just pancakes. However, their grilled cheese is worth mentioning.

The sandwich is made with cheddar and provolone cheese, bacon, and tomato on sourdough bread.

It's grilled to perfection and served with a side of fries. The portions are large, so come hungry.

The service is quick, and the staff is friendly. It's a great spot to grab a quick and satisfying meal.

3. 3 Arts Club Cafe

3 Arts Club Cafe
1300 N Dearborn St, Chicago, IL 60610 (Google Maps)

If you're looking for a great grilled cheese, head on over to 3 Arts Club Cafe. This chic restaurant and bar inside a furniture store offers a unique ambiance and exceptional food.

While the prices are a bit high, the quality of the food and service make it worth it.

The truffle grilled cheese is a must-try and the wine selection is fantastic.

The staff is knowledgeable and friendly, making for an enjoyable dining experience. Don't miss out on this hidden gem.

4. Eleven City Diner

Eleven City Diner
1112 S Wabash Ave, Chicago, IL 60605 (Google Maps)

Looking for a place to get your grilled cheese fix in a retro-style diner atmosphere with friendly staff and quality food in generous portions, look no further than Eleven City Diner.

This hidden gem offers a variety of menu options, including build-your-own grilled cheese and classic American diner meals.

Don't miss out on the Challah French toast or the Bad A** sandwich, both highly recommended by satisfied customers.

The atmosphere is lively with vintage decor and the service is attentive. Plan accordingly as this place can get busy during rush hours.

5. Lou Mitchell's

Lou Mitchell's
565 W Jackson Blvd, Chicago, IL 60661 (Google Maps)

Lou Mitchell's is a classic diner that's been serving up hearty breakfasts and lunches since 1923.

While their menu offers a variety of options, their grilled cheese is a standout.

Perfectly toasted bread and gooey cheese make for a delicious sandwich. The staff is friendly and the atmosphere is cozy, making it a great spot to grab a quick bite.

If you're in the mood for a classic grilled cheese, Lou Mitchell's is the place to go.

6. Manny's Cafeteria & Delicatessen

Manny's Cafeteria & Delicatessen
1141 S Jefferson St, Chicago, IL 60607 (Google Maps)

Manny's Cafeteria & Delicatessen is a Chicago institution that has been around since 1942. This old-fashioned cafeteria-style eatery serves up classic deli fare that is simply delicious.

While they are known for their corned beef and pastrami sandwiches, Manny's grilled cheese is definitely worth trying.

The sandwich is perfectly toasted with a generous amount of gooey melted cheese. The atmosphere is friendly and the portions are hearty.

Manny's is a must-visit for anyone looking for a great grilled cheese sandwich and classic deli fare.

7. TriBecca's Sandwich Shop

Tribecca's Sandwich Shop
2949 W Belmont Ave, Chicago, IL 60618 (Google Maps)

TriBecca's Sandwich Shop is a must-visit destination for grilled cheese lovers. Their unique and creative selection of vegetarian and non-vegetarian sandwiches will leave you wanting more.

The sides, especially the mac n cheese, are a must-try. The staff is quick and friendly, and the service is efficient.

The small interior space may be a little cramped, but it is worth it for the delicious food. The Cubano and the Roasted C.A.M. are highly recommended.

Don't forget to try their griddled rum cake and donuts for dessert. TriBecca's Sandwich Shop is definitely worth a visit for a satisfying and flavorful grilled cheese experience.

8. Egg Harbor Cafe

Egg Harbor Cafe
220 E Illinois St, Chicago, IL 60611 (Google Maps)

Egg Harbor Cafe is a great place for grilled cheese. The food is delicious and the service is wonderful.

The menu has a variety of options, so there is something for everyone.

The atmosphere is casual and family-friendly. The prices are reasonable for the quality of food.

Egg Harbor Cafe is definitely worth checking out if you're in the mood for a tasty grilled cheese sandwich.

9. Cafecito

7 N Wells St, Chicago, IL 60606 (Google Maps)

Cafecito is a Cuban coffee shop that serves up some of the best-pressed sandwiches in town.

The menu features a variety of delicious grilled cheese sandwiches, including the ropa vieja, provoletta, and jerk sandwiches. The Chivito is a must-try, loaded with steak, ham, turkey, bacon, and a fried egg.

The sandwiches are reasonably priced and come in generous portions. The cafe also offers deli-type sides and fantastic coffee.

The staff is friendly and helpful, and the service is quick. The space is small, so it's best to order ahead or grab food to go. Cafecito is a great spot for a quick lunch or a coffee break.

10. La Sandwichera Cafe

La Sandwichera Cafe
2721 W Division St, Chicago, IL 60622 (Google Maps)

La Sandwichera Cafe is a small sandwich shop that serves up some seriously tasty grilled cheese sandwiches.

With a simple and small menu, this place focuses on quality over quantity. The bread is perfectly crispy and the cheese is melted to perfection.

The staff is incredibly friendly and the prices are great. You can dine in or take your sandwich to go.

If you're looking for a quick and delicious bite to eat, La Sandwichera Cafe is definitely worth checking out.

11. Wyler Road

Wyler Road
3581 W Belden Ave, Chicago, IL 60647 (Google Maps)

Wyler Road is a must-visit place for grilled cheese lovers. This restaurant offers a great selection of hot and cold sandwiches, including options for vegans and vegetarians.

The cocktails here are also a highlight, with some unique and tasty options available.

The atmosphere is friendly and relaxed, making it a great spot to enjoy a meal with friends or family.

Don't forget to try the cheese curds and salt and vinegar kettle chips, they are a must-try. The patio is also a great place to enjoy some drinks in the summertime.

12. Boar's Head Cafe

Boar's Head Cafe
210 W Lake St, Chicago, IL 60606 (Google Maps)

Boar's Head Cafe is a must-visit for grilled cheese lovers. Their sandwiches are made with high-quality meats and cheeses, resulting in a heavenly taste.

The cafe is chill and friendly, and the staff greets you with a warm welcome. They offer vegetarian-friendly and gluten-free options, making it a versatile choice for all.

Although the prices are high, the quality of the food justifies it. The cafe is always clean and well-maintained, and the staff is attentive and efficient.

The takeout lunch options are great, and the coffee and desserts are a perfect way to end your meal. Boar's Head Cafe is a fantastic place to grab a quick bite, and you won't be disappointed with their grilled cheese sandwich.

13. Ceres Cafe

Ceres Cafe
141 W Jackson Blvd, Chicago, IL 60604 (Google Maps)

Ceres Cafe is a lively spot serving American eats in a unique location. The grilled cheese is a must-try, with perfect balance of crispy bread and gooey cheese.

The friendly service and decent prices make it a great spot for a quick lunch or happy hour drinks.

The atmosphere is bustling, with a mix of locals and visitors.

Don't miss out on the daily specials and homemade soups. Ceres Cafe is a hidden gem worth checking out.


The Clampdown
3474 N Clark St, Chicago, IL 60657 (Google Maps)

THE CLAMPDOWN is a must-visit for any grilled cheese lover. While they specialize in cheesesteaks, their grilled cheese sandwiches are equally impressive.

The menu offers classic and unique options, and the sandwiches are always made with fresh ingredients. Customers rave about the milkshakes, which come in a variety of flavors.

The service is friendly and efficient, and the outdoor dining area is a lovely spot to enjoy your meal.

Though it may be a bit pricey, the quality of the food and service make it worth it. If you're in the area, don't miss out on THE CLAMPDOWN's delicious grilled cheese sandwiches.

15. Harry's Sandwich

Harry's Sandwich
336 S Dearborn St, Chicago, IL 60604 (Google Maps)

Located in the heart of the city, Harry's Sandwich is a hidden gem that serves up some of the best grilled cheese sandwiches in town.

With a wide variety of bread options, cheeses, and toppings to choose from, customers can customize their sandwiches to their liking.

The staff is friendly and the service is fast, making it a great spot for a quick lunch or snack.

The cozy, old-timey atmosphere adds to the charm of the place. Harry's Sandwich is a must-visit for any grilled cheese enthusiast.

16. Danke

125 S Clark St, Chicago, IL 60603 (Google Maps)

Danke is a sandwich shop that serves high-quality grilled cheese sandwiches. Their bread is baked fresh and is perfect for a filling sandwich.

The ingredients are fresh and of high-quality, making their sandwiches a must-try.

They also offer a variety of other sandwiches, including the Veg sandwich, which is a favorite among customers.

The staff is friendly and welcoming, making for a pleasant experience. Danke is a great option for a quick lunch in the Loop that feels a little elevated.