exiledprincess

"That is easily double what you would pay if you went later in July." Again, the average hotel room goes for $200-300/nt. in Chicago during high season. You might possibly be seeing a discounted price for a really low tier hotel, perhaps not showing the city's accommodation taxes and fees, to come up with that low of a rate.

If the OP were to go to Indianapolis as I suggested above, they'll probably find an average hotel room to be $180-250/nt. during high season.

Again, the OP will need 2 rooms due to the size of the party. You will normally find that 2-3 individuals is normally considered the maximum occupancy in an average hotel room.

I should bring to everyone's attention about vacation rentals in Chicago. In order for a vacation rental of less than 30 days to be legal, it must be licensed with the City of Chicago.

In addition, some have been operating these in violation of leases and condominium association bylaws. There has been an ongoing crackdown on stopping these illegal units from operating - both by municipal authorities and condominium associations/building owners.

The Chicago Tribune had an article online dated March 12 about Airbnb rentals during this particular period of the Grateful Dead concert. I suggest anyone even contemplating getting a vacation rental read this. Not just for that period - but at any time. Do not put yourself in that position.

Here's another thought for the OP, if they were willing to do open jaw: Springfield, IL. Since you are both teachers, you might appreciate the Abraham Lincoln sites there. And you could take Amtrak up to Chicago easily on the 5th to enjoy a few days in Chicago before flying out.