We're planning a trip to NYC in June. I see that Playbill has Chicago tickets discounted throught Feb. at the moment, so I assume I can get discount tickets there later, but I'm wondering what the likelihood is that we could get Chicago tickets at the half-price booth in June. Does anyone know if that show is currently featured at the booth? Do you think I should just order them through Playbill if they offer them for the dates we'll be in town?
Thanks in advance for your help and opinions!

June is a really busy time for Broadway, but the show is older, so there might be discounts. If I were you I'd wait a little longer to see if anything opens up (maybe until March or April).

A lot depends on who's in that show. If it's someone with a strong following, it's sometimes harder. That happened when Usher was in the show. tdf.org/tkts has info on what's been at the booth recently.

You can also check how well the show is doing on www.playbill.com. Click on the link for Broadway Grosses and you can see how business is over a period of time instead of just one or two performances. Shows that are continually playing to empty houses are more likely to offer discounts.

Playbill also offers discounts for shows and restaurants if you register for a free account.

Thanks for the info everyone! I've bookmarked the site to check what's at the booths each week; that should be helpful in the coming months as we plan. Thanks McLaurie--I've never seen a link to that site before.

We still haven't made a decision as to whether we'll buy tickets early. We know we'll be at the Seaport booth at least once during our stay and thought we'd just see what's available that day. Looking at the list, we'll probably be able to find something we'll like. We already paid full price for Wicked tickets, and our companions may not want to see more than one show (I know, they're nuts), so for now, we're waiting.
Thanks again!