Right-side seats win for both segments of this flight. Takeoff offers Lake Michigan and Chicago's waterfront, while landing provides views of Florida's lake system and the Orlando metropolitan area. The right side captures the most visually distinctive features throughout the journey.
Flown ORD to ORL? Did we get it right?
Flight Path
Chicago to Orlando is 999 miles (1,607 km), a flight of about 2 hours 55 minutes.
The flight path crosses central Kentucky and Tennessee, passing over the Cumberland Plateau region. Notable features include the Tennessee River valley, scattered lakes in Kentucky, and the transition from Appalachian foothills to the flat terrain of central Florida. The landscape shifts from forested rolling terrain to increasingly flat agricultural and developed areas as you move south.
Great circle distance and headings ›Phase by phase

Takeoff from ORD
RIGHTRight-side seats offer views of Lake Michigan and the Chicago shoreline as the aircraft climbs southeastward out of ORD. You'll see the downtown Chicago skyline receding to the left while the lake dominates the right window.
Landing at ORL
RIGHTRight-side seats provide excellent views during the descent into Orlando Executive Airport. You'll see the transition from central Florida's lakes and wetlands to the airport approach, with views of the Orlando urban area and surrounding lakes.
Will your flight be in sunlight?
Pick a date and time in the Sun Map to watch the sun move across your whole flight.
About This Route
Which side of the plane should I sit on flying from Chicago Ohare International (ORD) to Executive (ORL)?
Sit on the Right side of the plane for the best views on flights from Chicago to Orlando. Right-side seats win for both segments of this flight. Takeoff offers Lake Michigan and Chicago's waterfront, while landing provides views of Florida's lake system and the Orlando metropolitan area. The right side captures the most visually distinctive features throughout the journey.
What can I see during takeoff from Chicago Ohare International in Chicago?
During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. Right-side seats offer views of Lake Michigan and the Chicago shoreline as the aircraft climbs southeastward out of ORD. You'll see the downtown Chicago skyline receding to the left while the lake dominates the right window. Notable sights include: Lake Michigan, Chicago downtown skyline, Illinois coastline, suburban sprawl extending south.
What can I see when landing at Executive in Orlando?
When landing at Executive (ORL), sit on the Right side for the best views. Right-side seats provide excellent views during the descent into Orlando Executive Airport. You'll see the transition from central Florida's lakes and wetlands to the airport approach, with views of the Orlando urban area and surrounding lakes. Notable sights include: Lake Apopka, Orlando metropolitan area, Florida wetlands and smaller lakes, downtown Orlando skyline.
How long is the flight from Chicago to Orlando?
The flight from Chicago Ohare International (ORD) to Executive (ORL) takes about 2 hours 55 minutes. The shortest flight path between them is 999 miles (1,607 km); winds and air traffic control usually add a few percent.
What does the Chicago to Orlando flight path pass over?
The flight path crosses central Kentucky and Tennessee, passing over the Cumberland Plateau region. Notable features include the Tennessee River valley, scattered lakes in Kentucky, and the transition from Appalachian foothills to the flat terrain of central Florida. The landscape shifts from forested rolling terrain to increasingly flat agricultural and developed areas as you move south.