**Edited to add: Please feel free to share your own notes or photos of how iPad Pro models fit into TB bags. 
I usually carry an iPad Pro (11", 4th gen, W: 7.02" - H: 9.74" - D: 0.23" - slightly bigger w/slim case) so I'll be trying it out in different TB bags.
First is a Side Kick (Black Ballistic) with size large double swivel carabiners. The SK will not zip (you can see the pink iPad case), but I'm considering options for hanging a bag from the airplane seat back and don't really need it to zip when holding the iPad.
*Edited to add: This model iPad does not fit into a zipped-up 400d Halcyon Side Kick either. (without an iPad case the SK will barely zip, but only if iPad is carefully inserted and SK is almost empty).
The set up pictured is my favorite in-flight option so far - I can leave my EDC items in the SK, then remove the iPad from my carry-on and temporarily slip it into the SK during flight, eliminating the need for an in-flight specific bag (or having to move items from EDC to an in-flight bag).

I usually carry an iPad Pro (11", 4th gen, W: 7.02" - H: 9.74" - D: 0.23" - slightly bigger w/slim case) so I'll be trying it out in different TB bags.
First is a Side Kick (Black Ballistic) with size large double swivel carabiners. The SK will not zip (you can see the pink iPad case), but I'm considering options for hanging a bag from the airplane seat back and don't really need it to zip when holding the iPad.
*Edited to add: This model iPad does not fit into a zipped-up 400d Halcyon Side Kick either. (without an iPad case the SK will barely zip, but only if iPad is carefully inserted and SK is almost empty).
The set up pictured is my favorite in-flight option so far - I can leave my EDC items in the SK, then remove the iPad from my carry-on and temporarily slip it into the SK during flight, eliminating the need for an in-flight specific bag (or having to move items from EDC to an in-flight bag).
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