Route Price Intelligence
Cheap Flights From Orlando to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
🔥 Fire DealFound 4d ago
$150Chicago fares from Orlando are down to $150, nicely under the usual $189-$318 range. You've got 9 date options from December through March to catch deep-dish pizza and the Art Institute downtown.
✓ 9 date combinations found at this price
Search Google FlightsTypical Price
$239
Great Deal
Under $188
Typical Range
$188 – $318
Lowest We've Seen
$57
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$183
Feb
$200
Mar
$329
Apr
$239
May
$239
Jun
$239
Jul
$239
Aug
$145
Sep
$145
Oct
$189
Nov
$238
Dec
$208
Cheapest Average Expensive
Best Time to Fly from Orlando to Chicago
The cheapest time to fly from Orlando to Chicago is typically August, when fares average around $145. The most expensive month tends to be March at around $329. For the best deals, consider flying in August, September, January.
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: April6,040 fares analyzedTypical low: $328
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