I drove in from Ohio and stayed at the host hotel. Check in was pretty easy except they changed my room to "an upgrade" but ended up being extremely loud because of where it was located. But it was roomy which was nice with my bike. At the expo there was a mandatory meeting that gave some general information about the race which was nice, you didn't get your ticket to pick your packet up until the end of the meeting. Packet pick up was well organized, you HAD to have your ID to get your packet. Then you could browse around the Expo. The expo had a lot of vendors, lots of merchandise to choose from. The only thing would have been a bit more merchandise with Chicago TRI on it.
There were pretty specific times to go to the transition area which was a decent distance from the hotel. The only thing that I didn't really understand was you could drop bike off day before but then you HAD to go back to transition in the morning several hours before the race, then transition closed.
The swim was good, you hop in, tread water until they blow the horn. The water was a little choppy but not too bad and there were volunteers at the end to help you out because the steps were a bit slippery. The bike route was good, nothing too hilly and you went under the city for a small portion which was pretty cool, messes with watch and mileage but worth it! The run was along the water and there were several water stations. The finish area was crowded but fine, food was OK, nothing memorable.
Overall the race was great, I would recommend it for anyone and do it again.