Last winter break, I posted something like this one and the thread garnered some truly outstanding possibilities, more than one of which I ended up doing. It worked out so well, I thought I would do the same thing here for summertime favorites.
A few of mine: the Printer’s Row Book Fair, a day at Arlington (either “Breakfast at Arlington” or actual races); the architectural boat tour, canoeing the river, The Folk and Roots Festival, eating rib tips from Lem’s off the hood of a car, and plenty of trips to Foster Beach and Morton Arboretum are all mainstays on the list. Taking the South Shore to the Dunes has been on there for a couple of years now, but we haven’t managed to make it happen yet. Maybe this is the year.
What else have you got?
The Harold Lounge 
The architecture boat tour is great. I took my sister and her boyfriend on it when she came out to visit.
Other than learning how to be a dad, I’m hoping to hit some of the fests, ribfest in particular. I’m also hoping to make it to at least one outdoor concert. Sadly, I’ll be out of town for the free July 2 concert (the Jayhawks and Everest) but there are others.