Pittsburgh was, contrary to popular belief, a very cool city surrounded by three rivers and tons of bridges, with cute neighborhoods, an old pharmacy-style ice cream parlor and cool converted spaces (from warehouses that have been made into lofts to churches that have been converted into bars and restaurants).
We had dinner at Brew Works, a former church that serves a wide variety of yummy fare and brews their beer right in the altar:
And we got to see Nik Wallenda, a seventh-generation descendant of the Flying Wallendas, walk across a 1000-foot tightrope above the Allegheny River about 200 feet in the air with no safety net.
Chicago was a huge and beautiful city, also surrounded by rivers and bridges, and so far, the most expensive destination we've hit. Parking was $25 for the afternoon, tolls getting in from Pittsburgh added up to almost $20 and the architectural boat tour along the river was $30 per person. It was a nice way to see the city, but Chicago is tough if you're trying to travel on a budget.
On the positive, I loved the silver bean in Millenium Park, we got to go to Taste of Chicago (where many popular restaurants shared their specialties), walked around Navy Pier (accurately described as a cross between Vegas and a country fair), strolled through the picturesque Old Town and picnicked along the shore of Lake Michigan.
The bottom line: this was a quick trip, but we'd definitely go back to Pittsburgh (and see the Andy Warhol Museum) and Chicago (to explore their art and culinary worlds).