Cheesie's Pub and Grub is one of The 15 Best Places for Grilled Cheese Sandwiches in Chicago.

1. Cheesie's Pub and Grub

8.8
958 W Belmont Ave (at Sheffield Ave), Chicago, IL
Sandwich Spot · Lakeview · 169 tips and reviews

Zenita L.Zenita Laws: Mac and cheese grilled cheese sandwich = best thing ever!!!! Try it!!!!

Courtney Y.Courtney Yocum: Grilled cheese, Mac & cheese, pizza, & beer...awesome joint close to the Belmont cta

Alisha W.Alisha Workman: Go there for the cheap, delicious drinks and the grilled cheese! Don't get the soups (even with that groupon...just forget em) and only get pizza if you can't handle epic grilled cheese. TENDERIZER!!!

3 Arts Club Cafe is one of The 15 Best Places for Grilled Cheese Sandwiches in Chicago.

2. 3 Arts Club Cafe

9.1
1300 N Dearborn St (at W Goethe St), Chicago, IL
Café · Gold Coast · 83 tips and reviews

Danielle E.Danielle Ebstein: This is a super posh place to eat. Fairly small menu but everything is delicious. Had the truffle grilled cheese and the eggs -- both were great. Atmosphere is definitely a plus!

Naz F. G.Naz F. Gérdabi: I can sit here for hours! gorgeous scenery, great wine options...and The Grilled Cheese

Yves GMYves GM: The grilled cheese and the granola are awesome 👌🏼

Lady Gregory's is one of The 15 Best Places for Grilled Cheese Sandwiches in Chicago.

3. Lady Gregory's

8.7
5254 N Clark St (at W Berwyn Ave), Chicago, IL
Irish Pub · Andersonville · 152 tips and reviews

Halleh C.Halleh Crockett: Try the ultimate grilled cheese!

MightybytesMightybytes: Kick back Lady Gregory’s relaxing library room while sipping one of over 300 whiskeys on their menu, or nibbling on a sophisticated grilled cheese sandwich, pot pie, or shepherd’s pie. Read more.

Patrick C.Patrick Cuttica: Been going here for a while - the whole menu is great. New favorite is the Ultimate Grilled Cheese. It's pretty incredible! Get the sweet potato fries as your side - the maple dipping sauce is tasty!

Four Moon Tavern is one of The 15 Best Places for Grilled Cheese Sandwiches in Chicago.

4. Four Moon Tavern

8.4
1847 W Roscoe St (at Wolcott), Chicago, IL
Pub · Roscoe Village · 52 tips and reviews

Monty E.Monty Edson: Get the grilled cheese sandwich - down with a good ale.

Amy D.Amy D: Best place to go for grilled cheese. Awesome decor.

Sabine C.Sabine Cummins: Go to Four Moon Tavern, order the Grilled Cheese with Swiss & Cheddar! Great beer selection too.

Robust Coffee Lounge is one of The 15 Best Places for Grilled Cheese Sandwiches in Chicago.

5. Robust Coffee Lounge

8.6
6300 S Woodlawn Ave, Chicago, IL
Coffee Shop · Woodlawn · 52 tips and reviews

MaegsMaegs: Great grilled cheese.

Ryan Jay O.Ryan Jay Owens: Perfectly buttered n crispy Challa bread toast on a yum yum nom nom Grilled Cheese w/ tomatoes and bacon. Caramel macchiato is pretty darn good. Headed to #LunchWithALeader nearby. Great find!

Justin H.Justin Holiman: Try either the BBQ Betty or the Brisket Grilled Cheese. Both outstanding!

Green City Market is one of The 15 Best Places for Grilled Cheese Sandwiches in Chicago.

6. Green City Market

9.3
1790 N Clark St (btwn Dickens Ave & LaSalle Dr), Chicago, IL
Farmers Market · Lincoln Park · 57 tips and reviews

Zachary K.Zachary Kraemer: If the grilled cheese lady is in the house, get in line, they're AMAZING

Luiz E.Luiz Eduardo: cookies and carnitas tacos, grilled cheese and creppes

Jason G.Jason Gardner: Everything is local and fresh! Worth a few extra bucks!

Restoration Hardware is one of The 15 Best Places for Grilled Cheese Sandwiches in Chicago.

7. Restoration Hardware

9.3
1300 N Dearborn St, Chicago, IL
Furniture and Home Store · Gold Coast · 13 tips and reviews

Melody L.Melody Legge: Lovely furniture. Adore the cafe. Courtyard style. Gorgeous area. Food was good. Grilled cheese, cheeseburger and fries were delightful. Prices pretty good. Will be back.

Holly R.Holly Ringle: Best grilled cheese ever! And you can't beat the ambiance.

John R D.John R Dallas Jr: From the day it opened, I remain a frequent diner, shopper, and evangelist here. There is simply nothing in Chicago as fascinating as this brilliant blend of culinary arts, commerce, and architecture.

Same Day Cafe is one of The 15 Best Places for Grilled Cheese Sandwiches in Chicago.

8. Same Day Cafe

9.1
2651 N Kedzie Ave, Chicago, IL
Café · Logan Square · 17 tips and reviews

Amy G.Amy Graff: Incredible sandwiches, creative sodas, and a few brunch items from the folks behind deeply missed Miko's Flipside. Rosemary grilled cheese is legendary.

Amy G.Amy Graff: The successor to Miko’s Flipside, this creative cafe makes it all from scratch, including house made sodas and baked goods. Love their red chimichurri scramble, grilled cheese, and luscious BLT.

Colin L.Colin Lee: Solid grill cheese - ice cream is homemade and fantasticb

Southport Grocery & Cafe is one of The 15 Best Places for Grilled Cheese Sandwiches in Chicago.

9. Southport Grocery & Cafe

9.1
3552 N Southport Ave (at W Addison St), Chicago, IL
Breakfast Spot · Lakeview · 90 tips and reviews

Serious EatsSerious Eats: Grilled Brie Sandwich at Southport Grocery is rightfully called "a grown up version of a grilled cheese" with a layer of gooey brie, fresh spinach and a delicious mess of sauteed mushrooms.

Mager M.Mager Mager: Insanely good bakery. Get the portobello grilled cheese and the vegan blueberry corn muffin.

Bitches Who BrunchBitches Who Brunch: Voted Best Family Brunch: A quaint, quiet shop that is nestled in the Southport Corridor, Southport Grocery is the perfect place to take your family for a well-balanced brunch.

RL Restaurant is one of The 15 Best Places for Grilled Cheese Sandwiches in Chicago.

10. RL Restaurant

9.2
115 E Chicago Ave (at Michigan Ave), Chicago, IL
American Restaurant · Streeterville · 115 tips and reviews

Stina P.Stina P.: Grilled Cheese and Tomato Soup. Undeniable RL decor. Top 3 Favorite. Got to keep the bread crumb catcher on my last visit.

Maya R.Maya Rubalcaba: Some of the best tomato soup and grilled cheese! Just love it and the service is amazing :) Read more.

Ghadi T.Ghadi Tayeb: I do not like what I ordered but maybe my choice was not that much I will try something else next time. The grilled cheese was so oily and I did nit like the tomato soup

BIG & little's Restaurant is one of The 15 Best Places for Grilled Cheese Sandwiches in Chicago.

11. BIG & little's Restaurant

8.2
860 N Orleans St (btwn W Chestnut St & W Locust St), Chicago, IL
Fast Food Restaurant · Near North Side · 140 tips and reviews

LSKLSK: Fried Grilled Cheese is a little greasy. But the Hawaii Five-O burger was great

AngelaAngela: The best fish tacos in Chicago with a large selection of different fish. The little samarai packs the perfect amount of heat. If your brave try the deep fried grilled cheese (it's surprisingly good).

Monti B.Monti Bray: Get the deep fried grilled cheese. Just do it. (PS cajun fries are also 💯)

Cleo's Bar & Grill is one of The 15 Best Places for Grilled Cheese Sandwiches in Chicago.

12. Cleo's Bar & Grill

8.1
1935 W Chicago Ave (at Winchester Ave.), Chicago, IL
Dive Bar · West Town · 51 tips and reviews

JenJen: Eat the grilled cheese, it's the best in the world. You will have dreams about it. Good and happy dreams.

Jenn F.Jenn Frank: best grilled cheese in town. it's all in the garlic aioli!

Jillian B.Jillian Burnickas: Outside patio is amazing in the summer. Excellent specials

Bar on Buena is one of The 15 Best Places for Grilled Cheese Sandwiches in Chicago.

13. Bar on Buena

8.2
910 W Buena Ave (at N Broadway), Chicago, IL
Bar · Buena Park · 78 tips and reviews

Thrashley N.Thrashley Nowak: This place can do no wrong. Small menu but its better that way. Everything is phenomenal. The grilled cheese with sweet potato fries is the best.

Reyna G.Reyna Griffin: get the Texas toast grilled cheese. best around!

Ghostly InternationalGhostly International: The B.O.B.'s amazing whiskey selection is one of the best in the city. Also, take a gander at the locally sourced food menu - try the Jalapeno Cheddarwurst with a Blanton's neat.

Handlebar is one of The 15 Best Places for Grilled Cheese Sandwiches in Chicago.

14. Handlebar

9.0
2311 W North Ave (btwn Oakley & Claremont), Chicago, IL
Vegan and Vegetarian Restaurant · Wicker Park · 129 tips and reviews

Denard M.Denard McNamara: The grilled cheese on multi grain w/ no tomato.....is AMAZING!!!!!!!

Jim P.Jim Peterson: Not a vegan so I order a grilled cheese and it was the best decision ever

Robert O.Robert Oswald: Best grilled cheese and staff in the city.

Bistronomic is one of The 15 Best Places for Grilled Cheese Sandwiches in Chicago.

15. Bistronomic

7.5
840 N Wabash Ave (at E Pearson St), Chicago, IL
French Restaurant · Near North Side · 39 tips and reviews

Time Out ChicagoTime Out Chicago: You’ve been here before—what was it that brought you back again? It’s not the room, and not the crowd. But it just may be the delicious grilled cheese du jour.

Serious EatsSerious Eats: The award for the butteriest, gooiest, and flat out fattiest grilled cheese in town goes to Bistronomic's grilled cheese. The cheese changes daily.

Carla H.Carla Ham: Best grilled cheese