Cafecito: a small café with good Cuban sandwiches and great coffee
Loumalnaties: Yes, it’s a chain but they have your typical deep dish style. But it’s better than the other chain. Don’t go to Giordanos.
Hancock Tower: go to the bar right before sunset. Just grab a drink at the bar and enjoy the view. Pricey drinks. Downtown.
Little Village
Café Cathedral: amazing chilaquiles and café de olla
Pacos Tacos: closest to what LA tacos can get to
Pilsen
Carnitas! at Carnitas Urupan or Carnitas Don Pedro
Skylark: bar with some awesome tater tots.
National Museum of Mexican Art
Cafe Jumping Bean
Harbees Tavern: bar and liquor store, sometimes they have DJs!
Caminos bar: go on Friday for their karaoke and get a michelada
Humboldt Park
Papas Cache: get the jibarrito (invented in Chicago) think of a torta but instead of bread it’s fried plaintain. Its heavy, I’d recommend splitting one and get some sides like arroz con gandules.
Café Colao: obviously get the café colao and the sandwiches, so good. My favorite ones are egg, ham and cheese and the chicken sandwich.
Ukrainian Village
Dark Matter/Star Café: Pick up some coffee beans. Try the Unicorn blood flavor.
Logan Square
99 Miles: amazing Cuban food. Get the ropa vieja or the lechon.
Revolution Brewery: Gotta try some local beers. I miss their Hibiscus Ale: Rosa.
Parsons Chicken: great chicken sandwiches, awesome location. Get the whiskey+pickle juice combo. They have Negronis too!
Wicker Park
Big Star: hipster taco spot but I approve. Get a margarita. If the wait is long, grab a beer at Boiler Room and get the PBJ special (Pizza, beer, Jameson). They have Jameson on tap! And some Jameson infused ice cream.
The Wormhole Cafe: Cool coffee shop with a dolerian inside (probably has parking tickets).
Bucktown/Sheffield Neighbors
Pequod's Pizza: One-of-kind Chicago deep dish pizza with caramelized crust.