Distance From Kissimmee Gateway Airport to Chicago Midway International Airport, ISM - MDW Distance

The distance from Kissimmee Gateway Airport (ISM) to Chicago Midway International Airport (MDW) is 998 miles or 1606 kilometers or 867 nautical miles.

The distance shown below is direct flight distance between airports. Straight-line distance does not account for the surface between the two points. It is the distance a bird or airplane would travel between the two points when flying above the surface. The straight line distance is the direct route between two points, regardless of whether or not there are roads that connect them.

---

How long does it take to travel from Orlando ( United States ) to Chicago ( United States )?

A one-way nonstop (direct) flight between Orlando and Chicago takes around 2 hours 17 minutes.

Estimated flight time from Kissimmee Gateway Airport, Orlando, United States to Chicago Midway International Airport, Chicago, United States is 2 hours 17 minutes under avarage conditions. Your actual flying time may vary depending on wind direction/speed or weather conditions. This calculation does not include the departure and landing times of the aircraft. In addition, it does not cover the person identity check, ticket check-in and baggage collection times at the airport.

Travel Distance Between the Airports • ISM - MDW

Kilometers		1606 km
Statute Miles		998 miles
Nautical Miles		867 nm
Avg. Time of Flight		2 hours 17 minutes

Kissimmee Gateway Airport to Chicago Midway International Airport Flight Route Map - ISM to MDW Flight Path

Location of Kissimmee Gateway Airport & Chicago Midway International Airport is given below.
Click the map to view Orlando to Chicago nonstop flight path and travel direction.

Click to see flight route on Google Map between Orlando, United States and Chicago, United States. .

Nonstop flight route between Orlando, United States and Chicago, United States.

Time Difference Between the Airports • ISM - MDW

Time difference between Orlando (United States) and Chicago (United States) is 1 Hours.
Chicago time is 1 Hours behind Orlando.

Location	Local Time
Orlando (United States)	2025-12-14, 17:10:41 EST
Chicago (United States)	2025-12-14, 16:10:41 CST

Why should you arrive 3 hours before international flight? Flyers who are traveling to an international destination should arrive at the airport earlier than domestic flyers. This is because international flights can have additional check-in requirements, like passport verification, that need to be completed before you receive your boarding pass.

Origin

Kissimmee Gateway Airport (ISM / KISM) Orlando, United States

Destination

Chicago Midway International Airport (MDW / KMDW) Chicago, United States