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When does the season at ITW usually end? What's the weather like in later September, in October, November?

It's open year round. The Ora wind is less in Oktober - Feb. Hope this helps.
Take care,
space

I went mid-September last year and managed 3 jumps a day; you just have to be up very early to be on the exit point at first light for the first of 2 jumps in the morning (account for 45 min taxi ride + 1 hr hike, or thereabouts, i.e. getting up around 4am, if not before). The Ora wind always made the site unjumpable after 11:30am / midday the times I've been there: it can easily gust >25mph so don't push it! The afternoon is generally a good time to catch up on sleep until 5pm, when (hopefully!) the winds are coming down and it's time to go for the evening load to jump around 7pm.

Everyone I know that's been in October had good weather.

Have a good time!

Thanks, guys, you rock!