American Food in Chicago Loop

Grilled cheese and tomato pesto soup anchor American food at Gayle V's Best Ever Grilled Cheese in Chicago Loop, IL, with pickup.

Order online

Sandwiches

Classic

$8.50

Butterkäse grilled cheese on white sourdough with fresh butter.

“I got the classic sammich and won some cheese curds on National Grilled Cheese day, all were delicious! The staff were very friendly. I highly recommend this!!”

Pulled Porker

$15.00

Pulled pork, barbecue sauce, and butterkäse fill this grilled cheese.

“Great lunch atmosphere! I tried the Pulled Porker and lemonade soda and really enjoyed both!”

On The Lighter Side

$12.00+

Small grilled cheese with tomato pesto soup and house-made potato chips.

“I’m always skeptical when a place says they make the best of what they’re offering. But Gayle wasn’t lying. The grilled cheese was perfect and so was the tomato soup. Don’t expect Campbell’s whatsoever. I got the “on the lighter side” which was perfect for a little bite before I headed home. So comforting. I hope they stay open forever!”

Cheeze & Thank You

$13.00

Vegan mozzarella, basil, and tomato jam make this grilled cheese.

“They were right! Best vegan grilled cheese I have ever had in my life.”

Breakfast

Breakfast Club #1

$15.00

Grilled cheese with double Butterkäse, pork sausage, egg, and maple syrup.

“This was my first time here. I came in with an hungry stomach and this restaurant made my experience wonderful. I ordered the Breakfast Club #1 and Chicago passion Black/Green tea. It was very delicious. There was also live feel good music. I will be visiting more often. Thank you Michelle. ❤️❤️”

Breakfast Club #4

$15.00

Egg, chorizo, cheddar, and hot sauce fill this breakfast grilled cheese.

Breakfast Club #3

$15.00

Grilled cheese with double white cheddar, egg, bacon, and maple syrup.

Breakfast Box Combo

$18.00

A breakfast grilled cheese sandwich comes with seasonal mixed fruit.

Tomato Pesto Soup

Regular Price - Cup of Tomato Pesto Soup

$5.00

A cup of tomato soup seasoned with pesto for herbal flavor.

“Recommend getting the little dunking soup for your grilled cheese, it's the perfect size for dipping. So tasty. Thank you Gayle! I loved it.”

Bowl of Tomato Pesto Soup

$8.00

Tomato pesto soup is vegetarian, gluten-free, and made without pine nuts.

“Great grilled cheese spot. The classic and a bowl of tomato soup. Chefs kiss.”

Mac and Cheese

Little Dipper

$2.50

A small side of house-made macaroni and cheese.

“Found this place while exploring the pedways. What a treat! The southport was very tasty. We also got the mac which was good, but glad we only got the little. It was just enough.”

From the Kitchen at Gayle V's Best Ever Grilled Cheese

American food at Gayle V's Best Ever Grilled Cheese includes grilled cheese sandwiches with meat or vegetable fillings, alongside tomato pesto soup and macaroni and cheese. Breakfast versions pair cheese with eggs.

Duke pairs Swiss cheese and ham with your choice of mustard or jam. The Jake combines Gouda, ham, and apple butter, while Margarita layers butterkäse with house-made basil pesto and fresh tomato.

Visit Gayle V's Best Ever Grilled Cheese in Chicago Loop, IL for pickup, dine-in, or delivery. Add Seasoned Fries to your meal: they're air fried, with house-made ketchup served on the side.

Frequently Asked Questions

What are your most popular American food options?

Our guests love these customer favorites. If you're visiting us these are some of the food options we recommend most often.

Classic — This sandwich layers Prairie Pure Butterkäse cheese in Bennison’s white sourdough, buttered with Nordic Creamery fresh butter.
Pulled Porker — Housemade pulled pork and barbecue sauce accompany double Butterkäse; carrot-and-apple slaw is offered as an optional addition.
River Valley — This grilled cheese features Prairie Pure Swiss cheese with sautéed River Valley mushrooms and smoked onion marmalade.
Regular Price - Cup of Tomato Pesto Soup — This cup holds tomato soup flavored with pesto, offering a savory side with a distinct herbal note.
On The Lighter Side — The lighter meal includes a small classic grilled cheese, a small tomato pesto soup without pine nuts, and house-made potato chips.

Do you offer delivery and takeout?

Yes! We offer both delivery and takeout for american food throughout the Chicago Loop area. Order your american food online for convenient pickup or delivery.