If you live in Chicago or it’s an easy trip in, it’s worth stopping by to buy the seats of your choice for what show you want to see.
If you live an hour or so out, are taking the train in, or paying for parking, and need to see the show the same day, then it’s not worth it.
I bought Wicked tickets for some friends online once online (a gift). $85 per seat dress circle. I drove them into Chicago for the show when the time came and on the off-chance seats were still available I checked (I was planning to eat and shop while they were at the show). Sure enough there were some limited view seats in dress circle on the opposite side where they were sitting and I bought a ticket at $38. That was a good deal!
Recently I wanted to see Phantom of the Opera before it closed so I took the train in hoping to get lucky again. I took the train in that time, stood in a short line but the lowest priced tickets available were $45 (dress circle again - different theatre). Since it was the only chance I had to see the show I paid the higher price, ate across the street at a really nice affordable diner, and watched the show. The view was awful. I couldn’t see anything over the people’s heads in front of me. Fortunately I had seen the show in Los Angeles years ago when Michael Crawford was still playing the phantom so I didn’t mind. But $45 for not being able to see was not a good deal.
I have come to the conclusion that I should save my money, earmark the shows I want to see, and then spend a Saturday in Chicago for fun stuff - planning to start at the box offices to buy the seats for the shows I want to see at a later time.
The ticketmaster fees are the equivalent of paying for train tickets in/out of Chicago and/or gas/parking for driving in. What I like about buying them at the box office is being able to see **all **the seats available for sale and picking from there - in a variety of price ranges for more than one night. Ticketmaster only shows you what they have available and they seem to push their preferences on you. Like with the Phantom seats. Everytime I searched online they kept giving me balcony seats way in the back for $56. At the box office I got the dress circle for $45. Once in the theatre, though, I get a better feel for which seats are worth the premium pricing, so that helps.
Good luck with your search and enjoy the show. It’s really wonderful!