No Chicago list is complete without a good hot dog spot. Yes, you could go to Portillos (we have no *beef* with them), but this is a local favorite. Get a char dog and ask for it "dragged through the garden" aka with all the good stuff on it.
At this point, you can be certain there is a Brad-shaped spot carved into a barstool at this local spot. Wrigley is probably the only other watering hole Brad has spent more time at during his time in Chicago. It is Barb's dream to to secure a spot on the Buck Hunter leader board.
It is Babs' quest in life to make a pie as good as Bang Bang. Brad is happy to research Bang Bang's many flavors in support of that goal — Brad's fav is key lime, Babs loves any of the fruit pies with the pastry crust. Their biscuits are also magical.
If you want to #doitforthegram, head to Cindy's, a rooftop bar in the Chicago Athletic Association (hotel). Enjoy tasty cocktails overlooking Millennium Park, home to the Bean aka the Cloud Gate sculpture. It's also walking distance to Sears Tower aka Willis Tower. (Yes, Chicago people are stubborn and like to call things by names that the world at large doesn't always use).
It's dark, it's musty, it's cash only and it is a Chicago delight. Across the street from Second City, this historic dive bar was the watering hole for Roger Ebert, Bill Murray, Stephen Colbert and more. The walls are filled with portraits of patrons and politicians, though the latter are not depicted as kindly. If you make a weekend out of your visit, see a show at Zanies just around the corner or of course the historic Second City.