Route Price Intelligence
Cheap Flights From Orlando to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
🔥 Fire DealFound 5d ago
$98Incredible $98 flights to Chicago on Frontier! This nonstop deal saves you 53% off typical rates. Perfect for a quick city break or connecting flights.
✓ 6 date combinations found at this price
Search Google FlightsTypical Price
$212
Deals From
$98
Usually Costs
$98 – $298
Lowest We've Seen
$57
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$353
Feb
—
Mar
—
Apr
$214
May
$164
Jun
$195
Jul
$206
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 $164. 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