For October travel, fly nonstop from Chicago to Orlando for $101 roundtrip on United.
Searching American, we found seats in basic economy, departing ORD on Tuesday, October 2, returning from MCO on Saturday, October 6.
United's basic economy fare does include both a carry on and personal item.
You'll find other dates are available for travel only on a handful of dates in early to mid October.
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.