Help with July Trip

Hi guys, I'm traveling to NYC from July 15th-17th. I want to see as many shows as possible and was wondering if someone could help me with a few questions.

1. My flight arrives at 09.45 on a Wednesday, and I'm guessing it's gonna take a long time to get to Manhattan (I'm traveling from Chile and security checkpoints for international flights are hell). I wanted to try and see a show on Wed's Matinee but since I don't know if I'll arrive on time I was wondering what the best option for getting a last minute ticket was, I was thinking TKTS of course, but what about the box office? Do they make discounts if I try to buy a ticket, lets say, an hour before the show? I wanna try to do It Shoulda Been You, because I love Sierra, but it'd be ok if I miss it.

2. The other shows I wanna see are Matilda, Fun Home and Les Mis. My question is, should I get tickets in advance? Or just try TodayTix a week before or the TKTS booth? I'm guessing I could rush Les Mis...

3. I'm flying to WI on Fri. 17th at 7 pm. Would you guys recommend going to Fri's Matinee of Wicked? I've never seen it, am I gonna have time to get my things from the hotel and get to LGA on time?

Thank you guys so much!

To clarify, if you have a valid discount code from BroadwayBox or wherever, you will get the discount at the box office close to showtime.

Dev, never once did she mention she wanted to see OTTC. Please stop self=promoting yourself on these threads, especially if you're not saying anything that appeals to what the poster wants.

"Dev, never once did she mention she wanted to see OTTC. Please stop self=promoting yourself on these threads, especially if you're not saying anything that appeals to what the poster wants."

OP wants to see as many shows as possible and also mentioned her interest in the TodayTix app. Just giving helpful advice on the app and an affordable show, which benefits us both.