Of course we recommend the place that we met - Navy Pier. Truly if you're looking to do something cool at Navy Pier, we recommend Flyover Chicago - https://www.experienceflyover.com/chicago/ We also recommend Billy Goat Tavern on the Pier, but they have many locations throughout the city
Where Dylan plays many weekends & always on St. Patrick's day!
Irish pub + Popcorn. What more could you want?!
Visit various museums - Field Museum, Shedd Aquarium, or Adler planetarium!