Route Price Intelligence
Cheap Flights From Orlando to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$206
Deals From
$180
Usually Costs
$180 – $338
Lowest We've Seen
$57
Based on 3,852 price pointshigh confidence
Monthly Price Guide
Jan
$410
Feb
$410
Mar
—
Apr
$181
May
$160
Jun
$191
Jul
$200
Aug
$189
Sep
$220
Oct
$230
Nov
$353
Dec
$402
Cheapest Average Expensive
Best Time to Fly from Orlando to Chicago
The cheapest time to fly from Orlando to Chicago is typically May, when fares average around $160. The most expensive month tends to be February at around $410. For the best deals, consider flying in May, April, August.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $6273 price checksWorst: $126