For September travel, fly nonstop from Chicago to Orlando for $105 roundtrip on American.
Searching American, we found seats in basic economy, departing ORD on Monday, September 10, returning from MCO on Monday, September 17.
Other dates are available for travel only on a handful of dates in mid September.
See our Chicago ORD fare listings for a complete look at current finds.
For a list of available accommodations for the above dates, check out Hotelwatchdog.