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

MDW Airport Page →
airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 2 1-stop flights
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 connections via 2 hubs
TPA Tampa ~4h 37m WN → Tampa (TPA) to Leesburg flights
RSW Fort Myers ~4h 55m WN → Fort Myers (RSW) to Leesburg flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Chicago to Leesburg
Connecting service available through multiple hubs.
+1h ahead

While no nonstop service exists between MDW and LEE, 1-stop connecting options are available.

Also explore MDW Routes LEE Routes MDW Live Flights LEE Live Flights MDW Delays
All flights from Leesburg (LEE) Leesburg to Chicago flights
Connections

Connection Landscape

1-stop and 2-stop options for MDW to LEE.
1-STOP
One-Stop Connections
2
Hubs
~4h
Fastest
~4h
Longest
TPA ~4h 37m RSW ~4h 55m
Verified with published schedule alignment and minimum connection time.
Connections computed from published schedules with minimum connection time verification. Use the interactive explorer above the fold to filter by airline, tier, and layover time.
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
MDW → LEE
80%
Generally reliable. Most flights run on time.
Departing
80%
Return
LEE → MDW
76%
Generally reliable. Most flights run on time.
Arriving
76%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays →
Know before you go

Travel Essentials

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

When it's 6:00 PM in Chicago, it's 7:00 PM in Leesburg.
Facts

MDW–LEE Quick Facts

Key statistics for the Chicago to Leesburg route.
Route details
Time difference+1 hour
Airlines (nonstop)0
1-stop connectionsAvailable
Origin: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
Destination: LEE
Full nameLeesburg International Airport
IATA / ICAOLEE / KLEE
TimezoneAmerica/New_York
Elevation76 ft / 23 m
FAQ

Frequently Asked Questions

Common questions about MDW to LEE flights.
Yes, 1-stop connections are available, ranked by layover time.
Leesburg is 1 hour ahead of Chicago.
Yes, return flights from LEE to MDW are available. Use the direction toggle at the top to view the return schedule.
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

1-stop connecting options are also available.