Chicago!

If you are driving then you can do both. You just need one night in Pittsburgh before heading onto Chicago.

If you are flying, then go to Chicago. As others have said, there’s much more to do in Chicago for 5 days. No contest.

If you are open to other suggestions, have you taken your kid to Canada? If you are driving from the dc metro area, it’s an easy drive to Montreal. You can head to Old Quebec a day or two later. Or you could pair Toronto with Niagara. If you are flying, the flights are cheap and quick. In addition to the usual suspect airlines, Porter flies out of Dulles.

And if you are up for an adventure, I’ve seen cheap flights to Dublin and Edinburgh this summer ($400-500). You can also look for air/hotel packages to keep costs low. Globus and Cosmos usually have 5 night packages and so do the major airlines. People will say it’s too short of a trip, but I disagree. (Then again, I’m the gal who took the train to Paris and back in one day during a weeklong business trip to London just so I could spend the day walking around Paris, shopping, and eating good food. I’m always up for a daytrip.)

Anonymous wrote:I love both places, but think Chicago has more to do for five days. We actually did a day and a half in Pittsburgh drove to Chicago three nights there one summer. I wish we had a few more days. Both cities have awesome ball parks if your kid is into that.

Do both!

Anonymous wrote:Chicago (but Pittsburgh is a fun, too)

+1

Chicago baby!

But I'm biased as I will always choose Chicago over almost any other metro city in US other than NYC.

I love both places, but think Chicago has more to do for five days. We actually did a day and a half in Pittsburgh drove to Chicago three nights there one summer. I wish we had a few more days. Both cities have awesome ball parks if your kid is into that.

Anonymous wrote:We’ve been to both in the summer. Chicago is better, much more to see and do.

+1. No contest.

Chicago is also a beautiful city. Pittsburg not so much.

I'm going the other way, we liked Pittsburgh better. Both have great ballpark areas, even if you aren't big baseball fans. Both have great boat tours.

Both are great places to go. If your kid likes to take time just strolling around neighborhoods (instead of seeing specific sights) then they’re both fine. If your kid likes to visit specific sights/museums, then Chicago has more things like that.

Chicago (but Pittsburgh is a fun, too)

We’ve been to both in the summer. Chicago is better, much more to see and do.

I love them both but I think Pittsburgh can be saved for a 2-3 day weekend and there’s way more to fill up 5 days with in Chicago. Chicago is also incredible in the summer. So that’s my vote!

They are both fine choices!

Whichever one they wanted to go to.

Never been to either, we’ll have 5 days in early or mid-July. Which would you choose, with a new high school grad?