Interesting that you mentioned, "I saw a video of it passing under that bridge in CHI". I'd be interested to know which bridge. The Lake Shore Drive bridge, which is the 1st bridge past the lock is probably 18' as are subsequent bridges.
We are 17' and slipped under and I was scared in doing it.
I can't imagine any NH (I thought New Hampshire as well) getting under the DOWNTOWN bridges. The Sanitary Canal is made for bigger boats.
Now, that said and keeping in mind the NH is a very creative company in building boats and seeing a Fleming 55 on the NY Canals at Whitehall it can be done.
The Fleming had a bridge that would drop down into the boat, allowing it to slip under the 17' bridges on the Champlain Canal.
NH could build a boat that could first drop its mast and then drop other parts to get under bridges.
That also might be why you can't find air draft figures. IF a NH is customized for its owner it won't fall into the 'norm'.
Find your boat and go from there. There are a number of ways to do the Loop so you can usually find a way around.
BTW, we should finish our 8yr Loop this yr.
Good luck.