I'm starting to wonder just how much travel we really can do, since it does add up (not just money but time), and at least to date, we really can't do long car trips, which are generally more economical. I think this might change, but the downside to being in Toronto is that you aren't a reasonable car ride to anywhere really. Certainly Buffalo isn't that far, but Buffalo...
Detroit and Ottawa are both within range, though I'd just prefer the train to Ottawa. In terms of Detroit, it would probably be simpler to fly to Windsor and then catch a bus across the border, and I'll investigate that as a serious possibility this fall (particularly since the Detroit Jazz Festival over Labor Day weekend is always a major event -- this year Ron Carter is the featured artist in residence). I suppose the train to Windsor is also an option, and it is an interesting trade off - 4.5 hours on the train for about $100 vs. $300 or so for a half hour flight (but then also time wasted in getting to the airport and going through security). It is possible to drive to Rochester or Ithaca, and I'll probably do that one of these days, but it isn't a particularly high priority. For all the other places, particularly Chicago, flying is just the better option.
Nonetheless, my wife and kids will be in Chicago for 2-3 weeks this August, and I'll swing by towards the end to pick them up. We are also tentatively thinking of going in October, though that will be somewhat dependent upon the school calendar.
Since I like to bundle things together, I have started looking into museums and theatre to keep me occupied on these trips. Unfortunately, it looks like on the August trip, I will just miss the Aaron Siskind exhibit at the Art Institute by just a week or so (and we missed it by about two weeks on the previous trip). So that's unfortunate, though I was able to check out a copy of Aaron Siskind 100, which appears to have most of the photos that would be in this exhibit. But I should be able to check out the Invisible Man exhibit, which looks interesting. It looks like I could probably skip the Cultural Center and the MCA in August.
In terms of theatre, I am quite likely to check out Maria Fornes' Fefu and Her Friends at Halcyon and possibly Freedman's Sister Cities. (I'd probably read the first act to make sure I want to see this play, but it generally had good reviews. Apparently, this will be the Chicago premiere of the work.)
If we do make it back in October, then for sure I want to see the Norman Lewis exhibit at the Cultural Center, and I'd probably swing up to the MCA on that trip. I would probably check out Posner's Life Sucks at Lookingglass, which is a follow up to Stupid F***ing Bird. (One of my major regrets from 2015 is that I didn't make it to the Victory Gardens' production of this play, but I think it will eventually hit Toronto.*)
Nonetheless, I should stress that I don't spend all my time looking up out-of-town events. I have enough trouble staying on top of everything going on in Toronto!
* Speak of the devil, I was checking out DPS, and someone (Vintage Productions?) has applied for the rights for this and it should take place in March 2017. I'm pretty excited about that, so now I can just focus on making Yankee Tavern happen, and of course see about staging some of my own work.