Route Price Intelligence
Cheap Flights From Orlando to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$339
Deals From
$230
Usually Costs
$230 – $457
Lowest We've Seen
$46
Based on 8,554 price pointshigh confidence
Monthly Price Guide
Jan
$477
Feb
$588
Mar
$250
Apr
$181
May
$204
Jun
$250
Jul
$250
Aug
$230
Sep
$437
Oct
$437
Nov
$517
Dec
$487
Cheapest Average Expensive
Best Time to Fly from Orlando to Chicago Midway
The cheapest time to fly from Orlando to Chicago Midway is typically April, when fares average around $181. The most expensive month tends to be February at around $588. 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: $4690 price checksWorst: $129