Originally Posted by
MSPeconomist
You could do MSP and have people stay/meet at either the JW or Radisson Blu at Mall of America. It's a short and pleasant light rail ride from the airport, with the light rail also connecting MOA to downtown. Of course, there is also a good selection of downtown hotels.
ORD and MDW are also connected to downtown and near north areas by public transportation, but IME it's less pleasant.
If MSP/Bloomington is an option, then ORD/Rosemont ought to be as well.
Honestly I have trouble understanding why O'Hare isn't the obvious choice here, as it has been for decades whenever far-flung people need to come together for a brief meeting. As a baseball fan I remember hearing for years about the owners always gathering at the O'Hare Hilton, to the extent where it was a bit of a thrill the first time I had my own business meeting there