The Guapichosa at Scofflaw
BREAKFAST
English muffin sandwich at Senza
Don’t know how the crisp biscuit enfolding bacon and Gruyère pillowed in a fried egg is gluten-free. Don’t care. It’s glorious. $5.50. 2873 N. Broadway, 773-770-3527, senzachicago.com
Breakfast sandwich at Balsan
It’s gorgeous until the first bite. Then the ciabatta with sunnyside-up eggs, house-cured speck, fontina, and puréed eggplant is a great, oozy mess.
$19. Waldorf Astoria Chicago, 11 E. Walton St., 312-646- 1400, balsanrestaurant.com
LUNCH
Sesame chili tuna at Soulwich
Few mortals finish this killer combo of spicy tuna, pickled carrots, daikon, pickle, lettuce, and cilantro-chili aïoli—best doggy bag fodder ever.
$7.75. 1634 Orrington Ave., Evanston, 847-328-2222, soulwich.com
Crispy Ciabatta Verdura at Fred’s Chicago
Portobello, eggplant, zucchini, red pepper, and onion mix with goat cheese on a pesto-smeared ciabatta. Very tony.
$17. Barneys New York, 15 E. Oak St., 312-596-1111, barneys.com
DINNER
Pulled pork and brisket at Smoque BBQ
Smoque makes a smart half-and-half—tender pulled pork and savory burnt-edged brisket—on one soak-up-the-sauce bun.
$7.95. 3800 N. Pulaski Rd., 773-545-7427, smoquebbq.com
“I don’t like red wine with my meal,” says Jane's Restaurant bartender Julia Rosenwinkle, “so I steer people toward a rye Manhattan.” She keeps her version simple, mixing Templeton Rye, bitters, and Vya sweet vermouth ($11). 
Photograph: Travas Machel
Grilled New York strip steak at Jane’s Restaurant
With a thin slice of meat and buttery mashed potatoes, this soul-warming sub begs to be enjoyed over a cocktail and conversation.
$15. 1655 W. Cortland St., 773-862-5263, janesrestaurant.com
DESSERT
Double Doozie at Sensational Bites
Warm chocolate chip cookies harboring vanilla buttercream frosting will make your inner child do cartwheels.
$2.50. 3751 N. Southport Ave., 773-248-2271, sensationalbites.com
Trail Mix Ice-Cream Sandwich at The Peasantry
Slabs of puffed wild rice bar studded with lime marshmallows and dried mangoes and Black Dog Gelato’s honey Greek yogurt sorbet—this treat is like nothing you ever bought from the ice-cream truck.
$6.50. 2723 N. Clark St., 773- 868-4888, thepeasantry.com
LATE-NIGHT
Bumpen Grinder at Pick Me Up Cafe
A baguette painted with a garlic purée, stuffed with grilled peppers, eggplant, onions, and tomatoes, and draped in provolone: a nocturnal indulgence you won’t regret.
$7.75. 3408 N. Clark St., 773-248-6613
Guapichosa at Scofflaw
Braised brisket, pork belly, and pork loin topped with crème fraîche and pimiento aïoli and served on buttery telera: an off-menu masterpiece. Scofflaw serves only five a night.
$12. 3201 W. Armitage Ave., 773-252-9700, scofflawchicago.com