Route Price Intelligence
Cheap Flights From Orlando to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$330
Deals From
$230
Usually Costs
$230 – $437
Lowest We've Seen
$46
Based on 8,581 price pointshigh confidence
Monthly Price Guide
Jan
$214
Feb
$164
Mar
$182
Apr
$195
May
$343
Jun
$415
Jul
$415
Aug
$415
Sep
$417
Oct
$469
Nov
$484
Dec
$457
Cheapest Average Expensive
Best Time to Fly from Orlando to Chicago Midway
The cheapest time to fly from Orlando to Chicago Midway is typically February, when fares average around $164. The most expensive month tends to be November at around $484. For the best deals, consider flying in February, March, April.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $4677 price checksWorst: $129