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

LEE Airport Page →
956 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.
956 mi 2h 17m nonstop -1h behind

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

On-Time Performance

What to expect at each end of your journey.
Outbound
LEE → MDW
82%
Generally reliable. Most flights run on time.
Arriving
82%
Return
MDW → LEE
66%
Moderate delays possible. Allow buffer time.
Departing
66%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays →

Other ways to reach Chicago from Leesburg

Nearby airports with service to Chicago Midway International Airport.
Metric LEE→MDW MCO→MDW LAL→MDW
Distance from LEE 41 mi 59 mi
Nonstop airlines 6 1
Weekly flights 63
Flight time 2h 17m 2h 40m 2h 9m
Airports within 200 miles of LEE with service to Chicago Midway International Airport.

Travel Essentials

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

When it's 6:00 PM in Leesburg, it's 5:00 PM in Chicago.
Distance & Flight Time
956 mi / 1,538 km
Nonstop flight time is approximately 2h 17m gate to gate.

LEE–MDW Quick Facts

Key statistics for the Leesburg to Chicago route.
Route details
Distance956 mi / 1,538 km
Flight time2h 17m
Time difference-1 hour
Airlines (nonstop)Charter / private
Origin: LEE
IATA / ICAOLEE / KLEE
TimezoneAmerica/New_York
Elevation76 ft / 23 m
Destination: MDW
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m

Frequently Asked Questions

Common questions about LEE to MDW flights.
Nonstop flights from Leesburg International Airport to Chicago Midway International Airport take about 2h 17m gate to gate. The route covers 956 miles.
Chicago is 1 hour behind Leesburg.
Nearby alternatives include MCO, LAL and TPA. 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.

Flights from LEE to MDW

Leesburg International Airport (LEE) and Chicago Midway International Airport (MDW) are connected through multiple connecting hub airports.

LEE to MDW Flight Duration and Schedule

Nonstop flight time from LEE to MDW is about 2 hours 17 minutes gate to gate. The route covers a distance of 956 miles (1,538 km).

Connecting Options and Alternatives

Nearby alternative airports include Orlando (MCO), Lakeland (LAL) and Tampa (TPA).