My Chicago Recommendations

Sep 11, 2021/ Updated: Mar 24, 2022

Here are a list of my favorite spots in Chicago.

Downtown

  • Cindys: a rooftop bar with a great view
  • 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.
  • 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.