Deal found on July 7, 2026
Chicago to Orlando
$203$43754% off
Round trip
Orlando usually costs about $497 round trip from Midway, so $203 on nonstop Southwest is a serious drop for a theme-park capital that never goes out of style. Plenty of runway to plan a Disney or Universal trip for later this summer through the holidays.
Travel dates
Aug 10 to Aug 19
Date options
5 at this price
Lowest we've seen
$67
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