Isn't Chicago still owed that pick though if it falls outside of the top 5? I don't even think we're allowed to trade a first rounder until like 2019 or something.
We aren't allowed to make a trade that could result in us not having a first-round pick in two consecutive future drafts. Now this is where it gets complicated:
We might convey a first rounder to Chicago in either 2016 or 2017 depending on our record. This means that we can't promise a pick in 2016 (because we might have to give away 2017) or in 2017 (because we might have to give away 2016). This is why we have the pick swap stuff with Philly. Now our 2018 pick (1-10 protected, if we convey to Chicago in 2016) or our 2019 pick (unprotected, if not already conveyed in 2018) will go to Philly as well. This means that 2018, 2019, and 2020 are also out of bounds for now. We can't trade an unencumbered first-rounder until 2021.
A summary, can the pick be traded:
2016: No. May go to Chicago (11-30). Conditional swap already with Philly if not conveyed to Chicago.
2017: No. May go to Chicago (11-30, if not conveyed in 2016). Conditional swap already with Philly if not conveyed to Chicago.
2018: No. May go to Philly (11-30, if 2016 goes to Chicago).
2019: No. Will go to Philly unless 2018 goes to Philly.
2020: No. Could be traded after 2018 if 2018 goes to Philly.
2021: Yes, but not together with 2022.
2022: Yes, but not together with 2021.
2023-: No. Cannot be traded due to seven-year rule.
So, basically, we can trade away either 2021 OR 2022 (or some conditional combination thereof that could result in only one pick being conveyed) and that's it. We can still make conditional pick swaps, however. In fact, there doesn't seem to be any reason we couldn't make a conditional pick swap on top of a conditional pick swap (e.g. if our pick is not conveyed to Chicago in 2016, we get the lower of our pick and Philly's pick. We could, on the condition that we do not convey to Chicago in 2016 trade the lower of our pick and Philly's pick to New Orleans for their 2016 pick, if it is lower than the one we have.) But that does get pretty hairy pretty quick.