Route Price Intelligence
Cheap Flights From Orlando to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$258
Deals From
$200
Usually Costs
$200 – $385
Lowest We've Seen
$57
Based on 8,567 price pointshigh confidence
Monthly Price Guide
Jan
$393
Feb
$410
Mar
$229
Apr
$160
May
$174
Jun
$220
Jul
$232
Aug
$209
Sep
$377
Oct
$385
Nov
$400
Dec
$420
Cheapest Average Expensive
Best Time to Fly from Orlando to Chicago
The cheapest time to fly from Orlando to Chicago is typically April, when fares average around $160. The most expensive month tends to be December at around $420. For the best deals, consider flying in April, May, August.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $5785 price checksWorst: $126