You do have too much per day so just prioritize it and do what you can.
Do take some warm clothes esp. for the architectural river tour. (It is super fun and amazing). I about froze in light PNW clothes in October on it.
I understand the museum is wonder–have been–but if I had your limited time and if the weather permitted I would choose most everything outdoors.
I think only day 3 is too much stuff. Day 1 is really just walking north on Michigan Avenue and maybe stopping in a few lobbies along the way to see whatever exhibits they might have. Or just to appreciate the architecture (the Tribune Building wall is embedded with stones from historic places). These are not places that you need to formally tour. Then finishing at the Hancock Center, which does take more time. On Day 2, the Architecture Foundation is right on the Riverwalk and the boat leaves from that area, so it’s all very close. After that Navy Pier can take as long or as little as they like. Day 3 is mainly walking around cool stuff in the park until you get to the museum. At that point, most everything in the daytime hours has been outdoors. I think the logistics were well planned, except the last few items on day 3 might be too much.
You could spend a whole day at the art museum. You have WAYYYYYY to much to do on each day of your visit. Way too much. What do you plan to do? Spend an hour in each place then Uber to the next? That makes no sense.
Look at Marilyns suggested plans…that have far less to do each day. Don’t try to cram a two week trip into three days.
I think your plan is manageable as well, as Day 1 is mostly stuff to walk by or quick stops into lobbies. Day 3 is the only day that I think is over booked as the museum alone could easily take the entire day. IMO, if you are looking for a quick in/out of the museum, it’s not worth the admission price. I also don’t think you’ll get anything new out of going to the Willis Tower after going to the Hancock. IMO, the Hancock has the better view of the city anyway.
I wasn’t offering a plan, but rather explaining why OP’s plan is doable. If you look on a map, everything on days 1 and 2 are very close to each other and totally walkable. Only the last part of Day 3 includes any distance, and even that is walkable if you have the energy since it’s only a mile from the Art Institute to the Willis (Sears) Tower. Maybe take a bus back up to the hotel at the end. Or the water taxi! https://www.chicagowatertaxi.com/
The Art Institute actually offers a plan if you only have an hour so they’re used to people who “hit and run.”
I also much prefer the view from the Hancock.
@Marilyn I think I’ll take out Rookery Building, Willis Tower, and Skydeck Chicago off of the list. Also, did you go on a river boat tour? If so, which one? I’m currently looking at the Chicago River Boat Architecture Tour.
@MoonKnight - I haven’t been on a river tour in decades but the one run by the Architecture Foundation is considered to be the gold standard in terms of architecture. But any of the tours that isn’t just “sightseeing” should be fine. Read reviews on TripAdvisor.
Thanks to everyone for your help. I think that finishes it. I have the whole trip pretty much planned. There isn’t really anything else for me to mention or ask. Thanks again!
Groupon has a Chicago Explorer Pass.
https://www.groupon.com/deals/go-city-card-chicago-explorer-pass