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Local picks in Chicago

Grilled cheese spots

Made for those who view a well-executed grilled cheese as the ultimate comfort food benchmark.

Based on 628 Opinions
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Updated May 2026
01
Afro Joes Coffee & Tea image 1
Afro Joes Coffee & Tea image 2
Afro Joes Coffee & Tea image 3
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Coffee shop shines with short rib grilled cheese on sourdough and crispy hash browns. Space feels calm and friendly, with live music and a dog run outside. Cozy seating past the barista invites chatting or working in a unique, art-filled setting.

Short rib grilled cheese stands out with its tender meat and sourdough bread base. The sandwich pairs well with crispy hash browns for a satisfying meal.

People are saying

"I loved the short rib sandwich, it was so satisfying."

"I found the coffee to be spectacular."

"You have to try the short rib grilled cheese; it's phenomenal."

Good to know

1

Live music happens every Saturday and Sunday, featuring various bands.

2

During summer, expect DJs and live music on weekends, especially on the patio.

3

Community events like movie nights and book readings are regularly hosted.

02
Moonflower image 1
Cocktail bar

Cocktail bar buzzes with dimly lit speakeasy vibe and a lively dance floor under a disco ball. Grilled cheese shines with a unique twist of pickles and sauce, perfect during happy hour. Live music and outdoor seating add to the warm, lively atmosphere.

Grilled cheese comes with an unexpected twist, featuring pickles, onions, and a sauce inside. Happy hour offers a deal with grilled cheese, a beer, and a shot for $6.

People are saying

"The food here was always incredible."

"It's a cool place with a dark, moody speakeasy vibe."

"Their grilled cheese had an unexpected and delicious twist."

Good to know

1

Happy hour runs from 4-7pm with great drink deals.

2

Moonflower hosts live music events on weekends.

3

Brunch drinks are charged separately from food.

03
Your Organic Inner G image 1
Vegan restaurant

Vegan spot shines with jerk vegan grilled cheese and fresh, natural dishes. Cozy, earthy vibe invites families with interactive games and a nutrition-focused library. Calm energy supports a health-conscious community.

Offers a jerk vegan grilled cheese that stands out for its flavor. Also serves grilled cheese with spinach paired well with mushroom coffee.

People are saying

"I found the food here to be delicious and filling."

"The dairy-free grilled cheese is so tasty, I ate it all."

"I found the jerk grilled cheese absolutely delicious."

Good to know

1

Food is cooked to order, so you must order ahead or be patient.

2

The restaurant offers both dine-in and take-out options.

3

They pride themselves on using no food additives and no soy.

04
Capriotti's Sandwich Shop image 1

Sandwich shop offers real carved turkey and generous fillings in a casual, well-lit space. Grilled cheese is melty and magical for kids. Atmosphere feels unwelcoming and can be disrupted by flies, with loud videos playing.

Melty texture stands out in the grilled cheese. Kids find it magical and awesome.

People are saying

"I found the sandwiches here to be really fresh and delicious."

"I was blown away by their awesome vegetarian options."

"The grilled cheese was melty and awesome."

Good to know

1

They have a $7.99 sandwich deal on weekdays for 8-inch subs, with different options each day.

2

They advertise a daily half sandwich special from Monday to Friday.

3

The portions are large, especially for the 18-inch subs.

05
Zeitlin's Delicatessen image 1

Cozy deli offers a family-friendly atmosphere with vibrant art and celebrity portraits. Grilled cheese shines on soft challah bread with tangy American cheese. Smooth, flavorful tomato soup complements the sandwich perfectly.

Challah bread makes the grilled cheese rich and soft. Tomato soup served alongside is smooth and flavorful, pairing well with the sandwich. Adding American cheese gives the grilled cheese a bit of extra tang.

People are saying

"These bagels are outstanding, crispy outside and soft inside."

"The sandwiches here were delicious and huge."

"The challah grilled cheese with tomato soup is decadent."

Good to know

1

There was no available parking on Clybourn without blocking traffic or risking a ticket.

2

They don’t accept cash; only card payments are accepted.

3

The only option for cream cheese on a bagel is to pay $8 for a tub.

06
Cheesie's Pub & Grub - Garfield Ridge image 1

Bar-cade features chalkboard walls and board games for fun and interaction. Grilled cheese sandwiches shine with creative names and fresh, buttery toasts. Upbeat indie music and multiple TVs create a laid-back atmosphere perfect for all ages.

Grilled cheese sandwiches here come with unique ingredients and creative names. They are fresh, cheesy, toasted with butter, and some include tasty breaded chicken tenders.

People are saying

"I thought the grilled cheese here was insanely amazing."

"You can draw on the walls and tables with chalk here."

"The atmosphere inside is really cool."

Good to know

1

They offer dollar cheese sandwiches this weekend with a special code.

2

Trivia happens on Thursdays at 8pm.

3

Bottomless brunch is available on weekends.

07
Osito's Tap image 1

Former speakeasy with a hidden entrance offers a cozy, intimate vibe with live mariachi music. Lamb Birria Grilled Cheese is a unique flavor standout, though pricey. Space feels creative and welcoming, perfect for fans of Mexican art and culture.

Lamb Birria Grilled Cheese stands out with its unique flavor and is a popular choice. The grilled cheese overall is well-made, though some find the $18 option just okay.

People are saying

"I found the food here to be really delicious."

"The bar staff here is so friendly and passionate about the drinks."

"I found the grilled cheese here to be excellent."

Good to know

1

Happy Hour runs from 4-7pm on weekdays with half-price appetizers.

2

Expect a casual dress code; no formal attire needed.

3

Credit cards and mobile payments are accepted, but cash is preferred for tips.

08
Bronzeville Hoagie & Panini image 1
American restaurant

Small sandwich shop shines with vegan grilled cheese and classic kid-friendly options. Walls tell stories through Black history photos and a historical mural. Friendly staff and awesome music create a warm, popular neighborhood vibe.

Offers a vegan grilled cheese panini with tomato basil pesto. Also serves classic grilled cheese sandwiches enjoyed by kids.

People are saying

"I found the sandwiches here to be top tier and delicious."

"The Wagyu Italian beef sandwich is packed with flavor."

"Their grilled cheese panini was delicious with pesto."

Good to know

1

There is now a lunch special available.

2

They offer two amazing tasting vegan options.

3

The line is often long, especially during lunch hours.

09
Mother's Ruin image 1

Small bar offers a relaxed vibe with indoor/outdoor space and a lively DJ. French onion grilled cheese shines with rich, savory flavor, paired perfectly with waffle fries and feta dip. Lighting sets a sexy, accepting atmosphere that keeps the crowd engaged.

French onion grilled cheese stands out with its rich, savory flavor. It pairs well with sides like waffle fries and feta dip for a satisfying meal.

People are saying

"The bar staff here are fantastic, friendly, and make you feel welcome."

"I thought the chicken sandwich here was the best I ever had."

"The French onion grilled cheese is unique and delicious."

Good to know

1

Happy hour runs daily from 4 to 7pm with great food and drink deals.

2

Brunch is served every day at Mother's Ruin.

3

Expect a lively atmosphere with frequent events and pop-ups.

10
Brûlée image 1
Restaurant

Warm, modern space with thoughtful decor sets a lively tone. Grilled cheese shines with smoked brisket, paired with classic tomato bisque. Music blends R&B at moderate volume, adding to the welcoming atmosphere.

Smoked brisket features prominently in the grilled cheese, paired with tomato bisque or tomato soup. Substitutions are not allowed, so sides come as is.

People are saying

"The food here is so flavorful and fresh."

"The shrimp and grits at brunch were some of the best I've ever had."

"The brisket grilled cheese has amazing flavor."

Good to know

1

Reservations are recommended for large groups or after 10 PM on weekends.

2

Expect a wait for tables, especially during peak brunch hours.

3

Brûlée enforces a strict 90-minute table limit for diners.

11
The Wolfhound Bar and Kitchen image 1

Cozy Irish pub with exposed brick walls and twinkling ceiling lights sets a warm vibe. Enjoy live traditional Irish music and sports on screen. Grilled cheese sandwiches come with perfect tomato soup, blending classic comfort with authentic drinks and American food twists.

Grilled cheese sandwiches come with a perfect pairing of tomato soup. The sandwiches look amazing and deliver exactly what you want in a grilled cheese.

People are saying

"The bar has a warm, lively, and welcoming atmosphere."

"I loved the pub food, especially the fish and chips."

"I wished I had ordered the grilled cheese."

Good to know

1

Reservations are recommended, especially on busy evenings.

2

Trivia night happens every Wednesday at 7:30pm with a lively atmosphere.

3

Live Irish music sessions occur on Thursdays, open to all who drop in.

12
Robust Coffee Lounge image 1

Coffee shop offers a cozy atmosphere with comfy booths and soft music. Brisket grilled cheese shines with rich brisket and bold flavors. A back room cigar bar adds an edgy feel to the space.

Brisket grilled cheese stands out with rich brisket and careful crafting. Other grilled cheese sandwiches come packed with flavor and quality.

People are saying

"It's a cozy spot with a warm, inviting vibe for coffee."

"The Cafe staff here is so friendly, they greet you by name."

"The brisket grilled cheese is amazing and packed with flavor."

Good to know

1

The coffee lounge closes at 3pm, limiting afternoon visits.

2

They host events and live music, enhancing the atmosphere.

3

Expect a variety of food and drink options available.

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