Explore Chicago!

We’ll definitely be keeping you busy at #ANationThatWorks—but we also want you to enjoy your time in our home town! Here are some of our team’s favorite sights and things to do around Chicago. And yes, we love food. 

Melissa, National Initiatives Director:

Amy, Director, Research & Policy Division of Heartland Alliance:

Chris Warland, Associate Director, Field Building:

  • At the Center for Intuitive and Outsider Art, Intuit, you can see a recreation of Chicago artist Henry Darger’s living and working space.
  • Café Iberico is a great tapas place. If you want to go off the beaten path, grab Korean food at the café in the back of the Joong Boo grocery store.
  • And I almost forgot: Hopleaf!

Caitlin, Policy Associate:

Carl, National Center on Employment & Homelessness Coordinator:

  • Walk, or bike, The 606—it’s a new, elevated trail that connects the city.
  • Pequod’s Pizza is the best deep dish in Chicago!
  • The Green Mill is one of the oldest jazz clubs in Chicago, and at Big Joe’s you can grab a drink and join in turtle racing.   

Tara, Workforce Research & Policy Fellow:   

  • Visit the Shedd Aquarium, located right by the Field Museum. You can see dolphins, beluga whales, sea lions, sea turtles, sharks, stingrays, and more.
  •  If you venture down to Hyde Park, home of the University of Chicago, Jimmy’s Woodlawn Tap is a great place to stop for a drink and a cheap bite to eat (I’d recommend their cheeseburger or grilled cheese sandwich). 
  • If you’re looking for something slightly more upscale in Hyde Park, the Promontory has great New American food (I’d also recommend their cheeseburger) and cocktails. Bonus: its second floor is a music venue.


Kyle, Workforce Research & Policy Assistant:

Amber, Communications Coordinator:

  • Mr. Brown's Lounge has the most amazing jerk chicken you will ever experience outside of Jamaica itself!
  • City Winery is an actual winery hidden in the West Loop. Be sure to sign up for a tour—it's an amazing look into what goes into making wine, especially in the middle of a metropolitan area.
  • Lincoln Park Zoo is a classic Chicago stop that is perfect for any age. It has everything: animals, food, and amazing views!