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10 Great & Gooey Grilled Cheeses to Try in Chicago, Mapped

Tomato soup is optional, but recommended

by Jeffy Mai
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by Jeffy Mai

Some of the best things in life are also the simplest. That's why the grilled cheese sandwich is a classic that's universally-loved by kids and adults alike. Because no matter the age, there's always comfort to be found in a bite of gooey melted cheese.

While your mom might've made grilled cheese using Kraft singles and Wonder Bread, Chicago restaurants are definitely stepping it up a notch. Chefs are elevating the sandwich game and showing off their creativity with footlong sandwiches, deep-fried wonders and more. It's safe to say that these creations will open your taste buds up to a new flavors when it comes to grilled cheese.

From the ritzy 3 Arts Club Cafe to unexpected joints such as BIG & little's and Edzo's, grilled cheese is no longer just a sidenote on menus. It's having its moment so check out the map below for 10 fantastic spots to get cheesy.

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3 Arts Club Cafe

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Luxury and decadence extend beyond the posh setting at Brendan Sodikoff's popular cafe inside Restoration Hardware. It’s also reflected in the food. Case in point: the grilled cheese, made with cheddar and truffle butter, is a fancy version that’ll leave you feeling like royalty.

1300 N Dearborn St, Chicago, IL, 60610
(312) 475-9116
(312) 475-9116
Yelp

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BIG & little's

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Patrons usually head to BIG & little’s in River North and Wicker Park for the fantastic fish tacos and burgers, but hidden away in the depths of the menu is a jaw-dropping deep fried grilled cheese. No fancy techniques here—just an old fashioned grilled cheese, with American or Swiss, thrown into the fryer to produce a golden, crispy ball of awesomeness. Not for the faint of heart, or anyone with high cholesterol.

860 N Orleans St, Chicago, IL, 60610
(312) 943-0000
(312) 943-0000
Huge Galdones

Also featured in:

Cheesie's Pub & Grub

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Few things in life feel better than demolishing a grilled cheese sandwich after an evening on the town. That’s why Cheesie’s, which is open until 5 a.m. on the weekend, is perhaps the ultimate late-night comfort spot. Feed that hunger with basics like The Classic (Merkt’s cheddar, American cheese, tomatoes, ham and bacon), or enjoy intriguing creations such as The Mac (Merkt’s cheddar, American cheese, housemade mac and cheese) and The Tradicion (Chihuahua cheese, jalapenos and chorizo). Cheesie's also has locations in Evanston and Wicker Park, and a food truck.

958 W Belmont Ave, Chicago, IL, 60657
(773) 388-1574
(773) 388-1574
Facebook

Also featured in:

Edzo's Burger Shop

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It takes a lot to say no to one of the juicy, tantalizing burgers at Edzo’s, but the surprising inside-out grilled cheese makes a compelling case. Owner Eddie Lakin raises the bar by putting shredded parmesan on the outside of the sandwich and griddling it. The result is a savory layer that adds another dimension to the simple-yet-irresistible classic.

1571 Sherman Ave, Evanston, IL, 60201
(847) 864-3396
(847) 864-3396
Facebook

Also featured in:

Gayle's Best Ever Grilled Cheese

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It’s not bragging if you can back it up, and Gayle Voss can definitely stake a claim to the best grilled cheese in Chicago. The sandwich maker was a longtime fixture at local farmers markets before opening her own storefront at Block 37 last year. Workers in the Loop have access to a number of different creations, ranging from the Southport (butterkase and smoked onion marmalade) to seasonal specials like The Abreo (cheddar, honey crisp apples and bacon onion jam) and The Sebastian (butterkase and lobster).

108 N State St, Chicago, IL, 60602
(312) 285-2202
(312) 285-2202
Facebook

Also featured in:

Hopleaf Bar

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Beer, mussels and frites are always requisites at Andersonville’s lauded beer bar but the CB&J sandwich shouldn’t be overlooked either. Ordinary becomes extraordinary thanks to cashew butter, raclette cheese and fig jam that provides a hint of sweetness. It’s served with Stilton mac for an unbeatable duo of cheesiness.

5148 N Clark St, Chicago, IL, 60640
(773) 334-9851
(773) 334-9851
Yelp

Also featured in:

Jerry's

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If there’s a sandwich you fantasize about, they can probably build it at Jerry’s. The sandwich specialist offers dozens of possibilities; the only limit is your imagination. Among the various grilled cheese options, the "Nutball" is a standout. The grand prize winner at this year’s Time Out Chicago Meltdown Fest is a satisfying blend of Swiss, provolone and cheddar that’s enhanced with cashew butter, applewood bacon, and mango-chipotle chutney dip.

5419 N Clark St, Chicago, IL, 60640
(773) 796-3777
(773) 796-3777
Facebook

Also featured in:

M Burger

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Although the Chicago burger chain keeps things relatively simple on its regular menu, fans in the know can order secret items for more variety. One of these unadvertised specials is a “grown-up” grilled cheese with avocado and tomato, but the real heartstopper is the option to order any sandwich “Roman-style.” Doing so replaces the bun with two grilled cheeses. Yes, you read that right. No, you probably don’t want to know the nutritional value.

161 E Huron St, Chicago, IL, 60611
(613) 487-6678
(613) 487-6678
Facebook

Also featured in:

The Fat Shallot

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One of the city’s finest food trucks has found a permanent home inside Revival Food Hall in the Loop. Now, visitors to downtown’s hottest lunch spot can nosh on Fat Shallot favorites like the grilled cheese, which packs ooey gooey melted muenster cheese with sautéed spinach and caramelized onions.

125 S Clark St, Chicago, IL, 60603
(773) 893-0826
(773) 893-0826
Facebook

Also featured in:

The Scout Waterhouse + Kitchen

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There can never be too much of a good thing, especially when it comes to grilled cheese. The Scout’s signature footlong sandwiches are impressive sights to behold and devour. They’re available in variations like The “Wolff” (double smoked bacon, jalapenos) and come served with tomato basil dip so that you can relive those childhood memories.

1301 S Wabash Ave, Chicago, IL, 60605
(312) 705-1595
(312) 705-1595
Yelp

Also featured in:

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3 Arts Club Cafe

1300 N Dearborn St, Chicago, IL, 60610

Luxury and decadence extend beyond the posh setting at Brendan Sodikoff's popular cafe inside Restoration Hardware. It’s also reflected in the food. Case in point: the grilled cheese, made with cheddar and truffle butter, is a fancy version that’ll leave you feeling like royalty.

1300 N Dearborn St, Chicago, IL, 60610
(312) 475-9116
(312) 475-9116
Yelp

BIG & little's

860 N Orleans St, Chicago, IL, 60610

Patrons usually head to BIG & little’s in River North and Wicker Park for the fantastic fish tacos and burgers, but hidden away in the depths of the menu is a jaw-dropping deep fried grilled cheese. No fancy techniques here—just an old fashioned grilled cheese, with American or Swiss, thrown into the fryer to produce a golden, crispy ball of awesomeness. Not for the faint of heart, or anyone with high cholesterol.

860 N Orleans St, Chicago, IL, 60610
(312) 943-0000
(312) 943-0000
Huge Galdones

Cheesie's Pub & Grub

958 W Belmont Ave, Chicago, IL, 60657

Few things in life feel better than demolishing a grilled cheese sandwich after an evening on the town. That’s why Cheesie’s, which is open until 5 a.m. on the weekend, is perhaps the ultimate late-night comfort spot. Feed that hunger with basics like The Classic (Merkt’s cheddar, American cheese, tomatoes, ham and bacon), or enjoy intriguing creations such as The Mac (Merkt’s cheddar, American cheese, housemade mac and cheese) and The Tradicion (Chihuahua cheese, jalapenos and chorizo). Cheesie's also has locations in Evanston and Wicker Park, and a food truck.

958 W Belmont Ave, Chicago, IL, 60657
(773) 388-1574
(773) 388-1574
Facebook

Edzo's Burger Shop

1571 Sherman Ave, Evanston, IL, 60201

It takes a lot to say no to one of the juicy, tantalizing burgers at Edzo’s, but the surprising inside-out grilled cheese makes a compelling case. Owner Eddie Lakin raises the bar by putting shredded parmesan on the outside of the sandwich and griddling it. The result is a savory layer that adds another dimension to the simple-yet-irresistible classic.

1571 Sherman Ave, Evanston, IL, 60201
(847) 864-3396
(847) 864-3396
Facebook

Gayle's Best Ever Grilled Cheese

108 N State St, Chicago, IL, 60602

It’s not bragging if you can back it up, and Gayle Voss can definitely stake a claim to the best grilled cheese in Chicago. The sandwich maker was a longtime fixture at local farmers markets before opening her own storefront at Block 37 last year. Workers in the Loop have access to a number of different creations, ranging from the Southport (butterkase and smoked onion marmalade) to seasonal specials like The Abreo (cheddar, honey crisp apples and bacon onion jam) and The Sebastian (butterkase and lobster).

108 N State St, Chicago, IL, 60602
(312) 285-2202
(312) 285-2202
Facebook

Hopleaf Bar

5148 N Clark St, Chicago, IL, 60640

Beer, mussels and frites are always requisites at Andersonville’s lauded beer bar but the CB&J sandwich shouldn’t be overlooked either. Ordinary becomes extraordinary thanks to cashew butter, raclette cheese and fig jam that provides a hint of sweetness. It’s served with Stilton mac for an unbeatable duo of cheesiness.

5148 N Clark St, Chicago, IL, 60640
(773) 334-9851
(773) 334-9851
Yelp

Jerry's

5419 N Clark St, Chicago, IL, 60640

If there’s a sandwich you fantasize about, they can probably build it at Jerry’s. The sandwich specialist offers dozens of possibilities; the only limit is your imagination. Among the various grilled cheese options, the "Nutball" is a standout. The grand prize winner at this year’s Time Out Chicago Meltdown Fest is a satisfying blend of Swiss, provolone and cheddar that’s enhanced with cashew butter, applewood bacon, and mango-chipotle chutney dip.

5419 N Clark St, Chicago, IL, 60640
(773) 796-3777
(773) 796-3777
Facebook

M Burger

161 E Huron St, Chicago, IL, 60611

Although the Chicago burger chain keeps things relatively simple on its regular menu, fans in the know can order secret items for more variety. One of these unadvertised specials is a “grown-up” grilled cheese with avocado and tomato, but the real heartstopper is the option to order any sandwich “Roman-style.” Doing so replaces the bun with two grilled cheeses. Yes, you read that right. No, you probably don’t want to know the nutritional value.

161 E Huron St, Chicago, IL, 60611
(613) 487-6678
(613) 487-6678
Facebook

The Fat Shallot

125 S Clark St, Chicago, IL, 60603

One of the city’s finest food trucks has found a permanent home inside Revival Food Hall in the Loop. Now, visitors to downtown’s hottest lunch spot can nosh on Fat Shallot favorites like the grilled cheese, which packs ooey gooey melted muenster cheese with sautéed spinach and caramelized onions.

125 S Clark St, Chicago, IL, 60603
(773) 893-0826
(773) 893-0826
Facebook

The Scout Waterhouse + Kitchen

1301 S Wabash Ave, Chicago, IL, 60605

There can never be too much of a good thing, especially when it comes to grilled cheese. The Scout’s signature footlong sandwiches are impressive sights to behold and devour. They’re available in variations like The “Wolff” (double smoked bacon, jalapenos) and come served with tomato basil dip so that you can relive those childhood memories.

1301 S Wabash Ave, Chicago, IL, 60605
(312) 705-1595
(312) 705-1595
Yelp

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