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

LEE Airport Page →
956 mi airlines 1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 6 1-stop flights Verified 1w ago
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  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

No flights match your filters.

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
Connecting service available through multiple hubs.
1 Flights/wk 956 mi 2h 17m nonstop -1h behind 6 1-stop hubs

While no nonstop service exists between LEE and MDW, connecting options are available through 6 hubs.

Also explore LEE Routes MDW Routes LEE Live Flights MDW Live Flights MDW Delays
Connections

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for LEE to MDW.
1-STOP
One-Stop Connections
6
Hubs
~4h
Fastest
~9h
Longest
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.
Alternatives

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 0 5 1
Weekly flights 1 54 –
Flight time 2h 17m 2h 40m 2h 9m
Orlando (MCO) to Chicago flights · Lakeland (LAL) to Chicago flights · Tampa (TPA) to Chicago flights
Airports within 200 miles of LEE 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.
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.
Facts

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)0
Weekly flights1 out
1-stop connections6 hubs
Origin: LEE
Full nameLeesburg International Airport
IATA / ICAOLEE / KLEE
TimezoneAmerica/New_York
Elevation76 ft / 23 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 LEE to MDW flights.
Nonstop flights from Leesburg International Airport to Chicago Midway International Airport take approximately 2h 17m. The route covers 956 miles.
There are approximately 1 nonstop flights per week from LEE to MDW.
Yes, 1-stop connections are available through SRQ, TYS, FLL, MIA, NAS and LAS. These options provide additional schedule flexibility.
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 ranges from 2 hours 17 minutes. The route covers a distance of 956 miles (1,538 km).

Connecting Options and Alternatives

6 one-stop connections are available, with the fastest taking approximately 4 hours via SRQ. Nearby alternative airports include Orlando (MCO), Lakeland (LAL) and Tampa (TPA).