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Local picks in Chicago

Grilled cheese spots

A simple, melted grilled cheese sandwich brings a sense of comfort and ease to a casual evening.

Based on 579 Opinions
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Updated May 2026
01
Your Organic Inner G image 1
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Vegan restaurant

Vegan restaurant offers a peaceful, earthy atmosphere with interactive games and a nutrition-focused library that create a welcoming, family-friendly vibe. The space feels cozy and heartfelt, encouraging calm and positive energy throughout. Food is made fresh to order with natural ingredients and no additives, supporting a health-conscious community.

Decor includes games that suit first dates well. Eating vegan tacos and vegan grilled cheese in the car adds a casual, fun vibe.

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 vegan grilled cheese and walnut tacos are so tasty."

"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.

02
Afro Joes Coffee & Tea image 1

Coffee shop occupies a unique space set back from the street in an old auto shop with Black art on walls and a spacious, comfortable layout. Atmosphere stays calm and friendly with live music and an outdoor area featuring a dog run. Seating includes a cozy spot past the barista for chatting, working, or relaxing.

Offers a cozy spot for coffee drinks with a relaxed vibe. Serves Afro Joes Coffee & Tea, making it a solid choice for a casual date or hanging out with friends.

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."

"The food and drinks here are amazing for Date Spots."

"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.

03
Moonflower image 1
Cocktail bar

Cocktail bar with dimly lit speakeasy vibe and dance floor featuring disco ball and neon lights creates a warm, lively atmosphere. Two distinct rooms separate music and dancing from intimate drink tables, while a downstairs bar offers a change in vibe. Frequent live music and outdoor seating add variety to the experience.

Intimate setting suits deep conversations and relaxed meals. Servers handle adjustments smoothly, even when guests are in a rush. The chicken sandwich stands out as a favored dish for date nights.

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 fun, comfortable spot for a great date."

"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.

04
Brûlée image 1
Restaurant

Warm, modern space with thoughtful decor and a spacious bar and waiting area creates a welcoming atmosphere. Music ranges from R&B at moderate volume to occasionally loud, influencing the energy. Tables are closely arranged, balancing elegance with a busy, lively vibe.

Reservations happen smoothly with quick seating. The atmosphere feels intimate and comfortable, fitting for couples and close friends celebrating special moments.

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 food here is delicious and flavorful for Date Spots."

"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.

05
The Wolfhound Bar and Kitchen image 1

Exposed brick walls and twinkling ceiling lights create a cozy, modern Irish pub atmosphere with a warm, inviting vibe. Live traditional Irish music and sports broadcasts add to the friendly, lively energy. The place stands out for its authentic drinks and excellent food with American 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."

"You have to try the Irish breakfast; the portions are huge."

"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.

06
Mother's Ruin image 1

Small bar with indoor/outdoor design and a small front patio creates a relaxed vibe. Lighting is amazing and music ranges from chill to loud with a live DJ. Crowd enjoys fun, curated music and a sexy, accepting atmosphere.

A spot with a great vibe for dates and casual drinks. It works well for couples looking to enjoy a relaxed evening together.

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."

"It's a great spot for date spots with incredible cocktails."

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.

07
Bronzeville Hoagie & Panini image 1
American restaurant

Small sandwich shop with about four tables features a historical mural and walls adorned with Black history photos. Atmosphere feels like a welcoming neighborhood hangout with awesome music and friendly staff. Lines often extend beyond lunch rush, reflecting steady popularity.

Sandwiches like turkey panini, turkey hoagie, and corned beef hoagie offer solid options. Cakes bring flavor variety and chili adds a savory touch.

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."

"These Date Spots have delicious, fresh ingredients and flavorful sandwiches."

"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.

08
Osito's Tap image 1

Former speakeasy with hidden entrance through a liquor store offers a cozy, intimate atmosphere with dark, moody decor and live mariachi music. The space feels unpretentious and creative, attracting those who appreciate Mexican art and culture. Conversations can be lively, sometimes making it hard to hear servers, but the vibe remains welcoming and relaxed.

A relaxed spot with a vibe suited for special dates and casual nights out. Walking distance access makes it easy for a quick, enjoyable evening.

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 cocktails here are amazing and expertly balanced."

"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.

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Chicago, Illinois

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