Route Price Intelligence
Cheap Flights From Orlando to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$340
Deals From
$230
Usually Costs
$230 – $457
Lowest We've Seen
$46
Based on 3,932 price pointshigh confidence
Monthly Price Guide
Jan
$462
Feb
$517
Mar
$618
Apr
$215
May
$200
Jun
$244
Jul
$250
Aug
$230
Sep
$437
Oct
$437
Nov
$537
Dec
$497
Cheapest Average Expensive
Best Time to Fly from Orlando to Chicago Midway
The cheapest time to fly from Orlando to Chicago Midway is typically May, when fares average around $200. The most expensive month tends to be March at around $618. 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: $4673 price checksWorst: $160