You would need to fly to a large Delta hub (ATL, MSP, JFK) early on a Saturday morning; and then fly around the Eastern half of the US until late at night. You would then repeat the process on Sunday, arriving back in Chicago late in the evening.

I ran a few scenarios. Looks like you can get 4 or 5 segments per day for about $250-$300. It would be very difficult to schedule 9 segments per day on Delta; and your plans would fall apart if even one segment was running late.

My advice is to plan on spending 4 days in the air at a cost of about $1250 if you want the 18 segments. Run the numbers yourself using Kayak. Use segments from Delta hubs to MCI, STL, FLL, MCO, BNA and BOS.

Bring a good book.