"Chicago is an old city full of activities like architectural boat tours and visits to the places where mobsters used to hide out. And if you want to continue this historical theme, consider eating at The Berghoff. This German spot opened in 1898, and still has an old-school bar/tavern feel. You can expect dishes like wiener schnitzel, sauerbraten, and a pretty fantastic reuben sandwich. Come here for a casual meal with someone who just spent the day listening to a tour guide talk like Al Capone. And hope they’re not inspired to practice their new gangster impression, or it’s going to be a long meal." - adrian kane, john ringor, veda kilaru