Open interactive map →Cheap flights from Chicago to Orlando
Fares on the Chicago to Orlando route vary noticeably by season and demand. Right now the lowest available price is €83. The route offers both direct and connecting options depending on the date. Booking further in advance typically unlocks lower prices, especially around school holidays and peak travel months. The calendar below maps out the cheapest and most expensive months so you can plan before committing to dates.
The cheapest fares on popular routes like this tend to sell out first, so it pays to book early once you spot a good price. Early-morning and late-night departures from Chicago are often priced lower than midday flights. SkyHopp refreshes fares regularly - if the current price doesn't fit your budget, check back in a few days as availability changes.
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Cheapest month to fly
- October 2026€831 stopCheapest
Based on tracked fares, October is the cheapest month to fly this route at around €83.
Prices last updated: September 2026
Entry requirements for United States
EU passportESTA required (visa-waiver)
US passportN/A (domestic)
Requirements vary by nationality and change without notice. Check requirements for your nationality →
About Orlando
Orlando is the world's theme-park capital - Walt Disney World, Universal Studios, SeaWorld, and LEGOLAND draw more visitors annually than almost any other destination. Orlando International Airport (MCO) handles massive transatlantic and domestic traffic; Kennedy Space Center is a one-hour drive east on the Space Coast.
Alternative routes
Other ways to reach Orlando
Frequently asked questions
How much does a flight from Chicago to Orlando cost?
The cheapest fare currently available from Chicago to Orlando is €83. Prices on this route vary by season, day of week, and how far in advance you book. The month-by-month price calendar on this page shows exactly when fares are highest and lowest, so you can pick the most cost-effective window before searching for specific dates. Fares are refreshed regularly as our flight partners publish new availability.
Are there direct flights from Chicago to Orlando?
SkyHopp tracks both direct and connecting flights from Chicago to Orlando. Connecting flights are often priced lower but add travel time due to the layover. Whether a non-stop option exists on specific dates depends on airline schedules - use the "Direct only" filter on the interactive map to see non-stop options, or check the booking site for a full breakdown by stop count.
When is the cheapest time to fly from Chicago to Orlando?
Prices on this route typically dip during shoulder-season months, away from school holidays and public holiday windows. Mid-week departures - particularly Tuesday to Thursday - tend to be cheaper than flights on Fridays and Sundays from Chicago. The month-by-month price calendar above is the fastest way to identify the cheapest window - look for the months with the lowest fares before committing to travel dates. Booking 3-6 weeks in advance generally offers the best balance of price and seat availability on this route.