Can’t speak to the bottle question. Haven’t ran the race since 2019 and don’t remember.

Spectating is super easy. Highly suggest staying in the Loop. You’ll pay a premium but the race starts and finishes in grant park and goes back and forth through the loop. Last time, I stayed at the Residence Inn. Race goes right past it on LaSalle.

Watching the start is borderline impossible but after briefly going through river north, racers will go southbound and then back northbound through the loop. Super simple to then take red line up to wrigley which I believe is roughly mile 8. Otherwise, the race comes back through the loop briefly around mile 13 before heading west. For the finish, again borderline impossible to get to the line as a spectator but you can cheer from a Michigan from mile 23 through 25.5ish.

Yeah pretty ez to stay downtown close to the race start. For a big city marathon, race day logistics are pretty easy. I've got friends on the southside (& used to live there myself) so I've always taken the red line in from 35th. Drops you right at the start but there aren't a lot of good hotel options in Chicago outside of the loop. You'll likely be able to walk to the start if you get a place there. Watching the race is easy. You're able to see a runner pass through multiple times just by sticking relatively close to the start/finish. 3 times- start/halfway/finish. You can also hop the red line north or south to get up to mile 8 or down to 23. Toughest part of the course imo is the stretch mile 13-20. Crowd is pretty sparse during that point so you could find a way over towards UIC & catch your runner there. Crowd support, in general, is much weaker than NYC & Boston.

Others have mentioned the logistics of where to stay and how to see so I’ll go on the other question. I don’t carry bottles but think the thought from things I’ve heard and seen is don’t plan on being able to bring filled bottles past security. I usually bring a few bottles through in the sat few years and haven’t had an issue but know that others have had to empty theirs before going through. So seems to be a crap shoot but I think it bottle is sealed it might be easier to talk your way through not tossing a bottle.

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