this is a price drop from two weeks ago!
Jetblue have a few roundtrip airfares travelling to and from Boston (BOS) and Chicago (ORD) for $88, nonstop! Spirit and United Airlines will have a similar airfare but Jetblue's economy fares are all main cabin, regular economy.
Departs BOS: Aug 29; Sept 5, 11-12, 18-19, 22
Departs ORD: Aug 7, 14, 15; Sept 5, 11-12, 18-19
Use dates and book directly with Jetblue [jetblue.com]
. For hotels, check out Hotwire's Hot Rates [hotwire.com]