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.
As someone who also lives in the MSP metro, I do think that it has a fair amount going for it. If a downtown hotel near nightlife, etc. is preferred, it's easy to get to downtown either on the every-10-minute light rail or via Uber or Lyft (or taxi.) Outside of the standard rush hours going to/from MSP wouldn't experience a lot of congestion either. There's also plenty of nice hotels near Mall of America that could work, many of which would have an airport shuttle and also be near the light rail to go to Minneapolis.
ORD/Rosemount is certainly more convenient if you're looking at a place to drop in and leave from easily, but ORD is so far from downtown Chicago if you want to actually experience Chicago.