August is the cheapest month to fly this route, with average fares around $160 round trip.
Average round-trip fares by departure month, based on current availability.
| Month | Avg Price | Lowest | Relative Cost | |
|---|---|---|---|---|
| May 2026 | $231 | $129 | Peak | |
| June 2026 | $196 | $85 | ||
| July 2026 | $191 | $113 | ||
| August 2026 | $160 | $113 | Best |
Departing on Wednesday offers the lowest average fares at $147. Saturday departures are the most expensive at $231, a difference of $84.
The best time to fly is August. Set up an alert and we'll notify you when prices drop.
Get Started Free →The cheapest month to fly from Chicago to Orlando is August, with average round-trip fares around $160. The lowest fare found in August is $113.
Wednesday departures are the cheapest, averaging $147 round trip. The most expensive day is Saturday at $231.
Based on current pricing trends, booking for August travel offers the best value. Avoid May if possible, as fares average $231 compared to $160 in the cheapest month. June is a solid middle-ground option at $196.
Flying in August instead of May can save you approximately $71 per round trip. The cheapest month averages $160 while the most expensive averages $231.
Airlines, flight times, price calendar, and more for Chicago to Orlando
View ORD → MCO Details