Open interactive map →Cheap flights from Orlando to Chicago
The Orlando to Chicago route currently shows fares from €79. Chicago is an accessible destination in United States from Orlando. Mid-week departures and shoulder-season months tend to keep prices lower on this route. Compare months in the calendar below to identify the cheapest window before locking in your booking.
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 Orlando 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€791 stopCheapest
Based on tracked fares, October is the cheapest month to fly this route at around €79.
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 Chicago
Chicago is the great American city that the coasts overlook - a dense, architecturally extraordinary lakefront city with world-class museums, deep-dish pizza, and jazz and blues venues that trace the music's northern migration. O'Hare (ORD) and Midway (MDW) together give the city one of the world's widest airport choices.
Alternative routes
Other ways to reach Chicago
Frequently asked questions
How much does a flight from Orlando to Chicago cost?
The cheapest fare currently available from Orlando to Chicago is €79. 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 Orlando to Chicago?
SkyHopp tracks both direct and connecting flights from Orlando to Chicago. 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 Orlando to Chicago?
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 Orlando. 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.