Originally Posted by
Uncle Nonny
Chicago is a great town with a lot to do. Check your bags with the bell desk when you check out. See the town, then go to the airport as you normally would. Don't over think the situation.
I agree. Leave bags at hotel, head into the city (El or Uber I'd hope would work). Return to hotel, claim bags, then check in at airport.
There's tons of information on things to do in Chicago over in the
Midwest forum. I'm sure if you post there, you'll get even more helpful advice.