Route Price Intelligence
Cheap Flights From Chicago to Orlando
Live pricing benchmarks, monthly patterns, and historical lows for this route.
🔥 Fire DealFound 1d ago
$203Orlando 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.
✓ 5 date combinations found at this price
Search Google FlightsTypical Price
$209
Great Deal
Under $118
Typical Range
$118 – $320
Lowest We've Seen
$57
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$353
Feb
—
Mar
—
Apr
$224
May
$155
Jun
$192
Jul
$200
Aug
$199
Sep
$208
Oct
$238
Nov
$320
Dec
$395
Cheapest Average Expensive
Best Time to Fly from Chicago to Orlando
The cheapest time to fly from Chicago to Orlando is typically May, when fares average around $155. The most expensive month tends to be December at around $395. For the best deals, consider flying in May, June, August.
Typical Price by Travel Month
Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route
Cheapest month: August43,893 fares analyzedTypical low: $190