Route Price Intelligence
Cheap Flights From Orlando to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$336
Great Deal
Under $248
Typical Range
$248 – $457
Lowest We've Seen
$46
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$457
Feb
—
Mar
—
Apr
$239
May
$219
Jun
$250
Jul
$250
Aug
$230
Sep
$348
Oct
$437
Nov
$537
Dec
$527
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 $219. The most expensive month tends to be November at around $537. For the best deals, consider flying in May, August, April.
Typical Price by Travel Month
Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route
Cheapest month: September14,428 fares analyzedTypical low: $417