Leesburg to Chicago (JYO–MDW) — Airlines, Schedules & Connections

JYO Airport Page →
567 mi airlines charter/private
On-time Some delays Frequent delays
Flight Schedule Charter / private Verified 1mo ago
Charter / private route. No scheduled airline service — operated by charter & private aviation.
Nonstop Charter / private 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

No flights match your filters.

No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.

✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Leesburg to Chicago
Flown by charter / private operators — no scheduled airline service.
567 mi -1h behind

JYO–MDW has no scheduled airline service; it is flown by charter / private operators.

Also explore JYO Routes MDW Routes JYO Live Flights MDW Live Flights MDW Delays
All flights from Chicago (MDW) Chicago to Leesburg flights
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
JYO → MDW
67%
Moderate delays possible. Allow buffer time.
Arriving
67%
Return
MDW → JYO
43%
Frequent delays expected. Consider flexible booking.
Departing
43%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays →
Alternatives

Other ways to reach Chicago from Leesburg

Nearby airports with service to Chicago Midway International Airport.
Metric JYO→MDW IAD→MDW DCA→MDW
Distance from JYO – 11 mi 32 mi
Nonstop airlines – 16 3
Weekly flights – 4 45
Dulles (IAD) to Chicago flights · Washington (DCA) to Chicago flights · Baltimore (BWI) to Chicago flights
Airports within 200 miles of JYO with service to Chicago Midway International Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
-1h
Chicago is 1 hour behind Leesburg.
JYO: EDT · MDW: CDT

When it's 6:00 PM in Leesburg, it's 5:00 PM in Chicago.
Distance & Flight Time
567 mi / 913 km
Facts

JYO–MDW Quick Facts

Key statistics for the Leesburg to Chicago route.
Route details
Distance567 mi / 913 km
Time difference-1 hour
Airlines (nonstop)Charter / private
Origin: JYO
Full nameLeesburg Executive Airport
IATA / ICAOJYO / KJYO
TimezoneAmerica/New_York
Elevation389 ft / 119 m
Destination: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
FAQ

Frequently Asked Questions

Common questions about JYO to MDW flights.
Chicago is 1 hour behind Leesburg.
Yes, return flights from MDW to JYO are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include IAD, DCA and BWI. See the Alternatives section for a full comparison.
Click the 'Search Flights' button to check availability and prices on Google Flights. You can also compare airlines and schedules on this page to find the best option.
See the On-Time Performance section for the latest delay data at both airports. This shows departure and arrival reliability to help you plan.
Route data is updated regularly from official airline schedules. On-time performance data comes from recent airport delay snapshots.

Connecting Options and Alternatives

Nearby alternative airports include Dulles (IAD), Washington (DCA) and Baltimore (BWI).