Route Price Intelligence
Cheap Flights From Orlando to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
🔥 Fire DealFound 5d ago
$62🔥 Incredible Orlando to Chicago deal! Just $62 roundtrip on Frontier - that's 70% off normal prices. Great for exploring the Windy City!
✓ 6 date combinations found at this price
Search Google FlightsTypical Price
$209
Deals From
$188
Usually Costs
$188 – $298
Lowest We've Seen
$57
Based on 813 price pointshigh confidence
Monthly Price Guide
Jan
$374
Feb
—
Mar
—
Apr
$205
May
$169
Jun
$191
Jul
$200
Aug
$189
Sep
$208
Oct
$238
Nov
$332
Dec
$415
Cheapest Average Expensive
Best Time to Fly from Orlando to Chicago
The cheapest time to fly from Orlando to Chicago is typically May, when fares average around $169. The most expensive month tends to be December at around $415. For the best deals, consider flying in May, August, June.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $6270 price checksWorst: $126