Chicago’s 12 Best Sandwiches — 2019 Edition

Look, I get it. You’re aiming for that bathing suit body, and you’ve sworn off carbs. But summer is made for the eating of sandwiches, and a leaf of romaine just isn’t going to cut it as a delivery vehicle when you’re packing up food for the beach or Ravinia. So, grab two slices of bread (or a bagel, bialy, roll, or pita), some carefully sourced proteins and veggies, a slice of cheese (stinky or otherwise), your favorite condiments, et voilà! One of life’s great and most satisfying edible joys: the perfect handheld meal, to be consumed on the run at lunch hour or sitting at an outdoor café table with a glass of rosé. These 12 places are making a run for the top.

(For a previous “Best Sandwich” list, check out this column from 2018. Still delicious.)

This Little Piggy


810 Dempster St., Evanston

Star Sandwich: Cubano, $9.95

Best Sandwiches: Hewn
Hewn’s Cubano (Photo by Julie Chernoff.)

My favorite bakery interprets this Cuban favorite by stuffing their Hewn ciabatta roll with house-made pulled pork (with just a touch of sweetness) and adds artisanal ham from Iowa; slices of swiss cheese; crunchy disks of their own bread-and-butter pickles; and a generous drizzle of yellow mustard. But the alchemy happens when the sandwich emerges from the panini press, the cheese melting into every crevice and the bread compressing and attaining maximum crustiness in the heat. It’s a damn good sandwich.

Piggie Smalls

Wells Street Market, 205 W. Wacker Drive, Chicago

Star Sandwich: Greek Sausage Gyro, $7.99

Best Sandwiches: Piggie Smalls
Piggie Smalls’ Greek Sausage Gyro (Photo courtesy of Piggie Smalls.)

James Beard Award-winning chef Jimmy Bannos Jr. has a pretty sweet side hustle, and the pedigree of this fast-casual market stall is reflected in the careful sourcing of ingredients. I’m particularly digging this gyro with Bannos’ made-in-house Greek pork sausage, layered with butter lettuce leaves, paper-thin slices of sweet onion and tomato, and a generous slather of creamy, garlicky tzatziki sauce, all on a griddled Greek pita.

Tempesta Market

1372 W. Grand Ave., Chicago

Star Sandwich: Southside Johnny, $14

Best Sandwiches: Tempesta Market
Tempesta Market’s Southside Johnny (Photo courtesy of Tempesta Market.)

This family-owned deli market is turning it OUT. Griddled Publican Quality Bread sourdough surrounds thinly sliced, house-made porchetta; Brun-uusto cheese from Wisconsin; broccolini roasted with a good glug of olive oil; herby, vinegary chimichurri sauce; and shaved pickled fennel. As if that wasn’t enough, they infuse the porchetta jus with rosemary and serve it on the side for dipping. You can taste the love in this one.

One Fish, Two Fish


1931 W. North Ave., Chicago

Star Sandwich: Tuna Melt, $8

Best Sandwiches: Brobagel
Brobagel’s Tuna Melt (Photo by Billy Jacobs.)

I’ve always loved a good tuna fish sandwich, but it turns out that if you slap it on a sesame seed bagel with sliced tomatoes, garlic aioli, and melted manchego cheese, it can exceed your wildest expectations. This is a 21st century tuna sammy. Who knew you could improve on the original? A good tuna melt will never go out of style. 

Loud Mouth

Politan Row, 111 N. Aberdeen St., Chicago

Star Sandwich: Lobster Roll, $19

Best Sandwiches: Loud Mouth
Loud Mouth’s Lobster Roll (Photo by Julie Chernoff.)

Life and business partners Grey and Lauren Ingram started with food bikes, but they’ve really found a thriving home at Politan Row in the West Loop. They might specialize in house-made, “ginormous” sausages, but found that their special Lobster Roll became their biggest seller and scored a permanent place on the menu. The butter-dipped Gonnella roll is toasted and filled with succulent morsels of Prince Edward Island lobster and simply drizzled with Old Bay aioli. The contrast of textures and temperatures makes for a happy mouth explosion. Let’s go, summer!

Mooveable Feast 

Benny’s Chop House

444 N. Wabash Ave., Chicago

Star Sandwich: Steak Sliders, $12.99

Best Sandwiches: Benny's Chop House
Benny’s Chop House’s Steak Sliders (Photo by Mistey Nguyen.)

Good things happen when you belly up to the bar in this River North stalwart, starting with this fabulous bargain: two thick-cut USDA Prime beef tenderloin sliders on house-made, buttered, and grilled brioche buns, with aged Cheddar cheese, sweet caramelized onions, and a ladle of horseradish cream, served with a basket of delectably crisp fries tossed with parmesan and chopped parsley. Get in my belly.


449 N. Clark St., Chicago

Star Sandwich: Pepito, $12

Almost impossible to single out one great sandwich when truly, it’s a spin of the wheel. But I’ll try: Fresh out of the wood-burning oven comes superstar chef Rick Bayless’ masterpiece of a torta, an umami torpedo of braised, melt-in-your-mouth short ribs piled with caramelized onions, Jack cheese, saucy black beans, and pickled jalapeños for a much-needed acidic bite.

Gotta Fly

Fry the Coop

Wells Street Market, 205 W. Wacker Drive, Chicago; 5128 W. 95th St., Oak Lawn; 623 W. North Ave., Elmhurst

Star Sandwich: Nashville Fried Chicken Sandwich, $10.49

Best Sandwiches: Fry the Coop
Fry the Coop’s Nashville Fried Chicken Sandwich (Photo by Kailley Lindman.)

How to make a kick-ass fried chicken sammy: Prepare the chicken fresh every day, not a frozen clucker to be found anywhere. Spice the breading just right. Offer a variety of heat levels (from “Country — no heat” to “Crazy — call 911”). Put your perfectly fried chicken on a buttered and griddled, pillowy soft brioche bun and top it with creamy coleslaw, sweet/spicy bread-and-butter pickles, and a dollop of special sauce. Go forth and serve.

The Ruin Daily

328 S. Jefferson St., Chicago

Star Sandwich: The Craig, $12

Best Sandwiches: The Ruin Daily
The Ruin Daily’s The Craig (Photo courtesy of The Ruin Daily.)

This West Loop shop has quickly become a local favorite, not in little part because of the inventive sandwich combinations available (and did I mention they serve cocktails at their “Day Bar?”) Apparently, I share a favorite sandwich with owner Craig Golden, namesake of this tryptophan-heavy offering. Marble rye bookends sliced roast turkey, cranberry sauce, whipped feta cheese, some baby kale for green crunch, and a garlic aioli to pull it all together. Kettle chips included!

The Smith

400 N. Clark St., Chicago

Star Sandwich: Grilled Chicken and Burrata, $16

Best Sandwiches: The Smith
The Smith’s Grilled Chicken and Burrata (Photo courtesy of The Smith.)

One of my favorite NYC haunts has ventured west to Chicago’s River North, and I’m pretty happy about it. Consider this grilled chicken sandwich, often a peace offering to those afraid of flavor. Here, the chicken melds beautifully with unctuous burrata, savory-sweet tomato jam, herbaceous basil aioli, and peppery arugula, all on a scrumptious ciabatta roll (courtesy of the great Greg Wade of Publican Quality Bread).

Veggie Love

The Fat Shallot

2468 N. Clark St., Chicago; Revival Food Hall, 77 W. Adams St., Chicago

Star Sandwich: Grilled Cheese, $7

Best Sandwiches: The Fat Shallot
The Fat Shallot’s Grilled Cheese (Photo courtesy of The Fat Shallot.)

Grilled cheese can be delicious even in its simplest form, using just white or wheat bread, soft butter, and American cheese. But it gets a serious upgrade at Fat Shallot with crusty sourdough bread, oozing Meunster cheese, sautéed spinach, and caramelized onion. Trust me — you won’t be mad about it.


74 W. Illinois St., Chicago

Star Sandwich: Eggplant Sabich, $12.95

Best Sandwiches: Ema
Ema’s Eggplant Sabich (Photo by Christina Slaton.)

Vegetarians won’t feel like second-class citizens when biting into this textural wonder. Smooth hummus coats the inside of chef CJ Jacobson’s house-made pita bread, which is then stuffed with roasted eggplant, chunky Israeli salad (chopped cucumber/tomato/onion/bell peppers), pickled turnips, hard-boiled eggs, and a schmear of garlic tahini. Market greens are served on the side, but no one will judge you if you add a side of Crispy Potatoes with scallion crema.

Julie Chernoff, Make It Better’s dining editor since its inception in 2007, graduated from Yale University with a degree in English — which she speaks fluently — and added a professional chef’s degree from the California Culinary Academy. She has worked for Boz Scaggs, Rick Bayless, and Wolfgang Puck (not all at the same time); and counts Northlight Theatre and Les Dames d’Escoffier International as two of her favorite nonprofits.