Orlando to Chicago (ORL–MDW) — Airlines, Schedules & Connections

ORL Airport Page →
983 mi airlines charter/private 2/wk
On-time Some delays Frequent delays
Flight Schedule No service Verified 30m ago
Also flown by charter / private operators.
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
Orlando to Chicago
Connecting service available through multiple hubs.
1 Airlines 983 mi 2h 38m nonstop -1h behind

ORL–MDW had nonstop service from Nationwide Airlines, last on the schedule in June 2026. There's no nonstop on it right now, so today you'd fly it with one stop. The connecting options below are sorted by layover. Nonstop, it's about 983 miles in 2h 38m.

Also explore ORL Routes MDW Routes ORL Live Flights MDW Live Flights MDW Delays
All flights from Chicago (MDW) Chicago to Orlando flights
Carriers on this route

Airline Landscape

Carriers that operated nonstop ORL–MDW service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
CE Nationwide Airlines 1 – – – – –
Alliance coverage
Unaffiliated: CE (1 flights/wk, 100%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.
Connections

Connection Landscape

1-stop and 2-stop options for ORL to MDW.
1-STOP
One-Stop Connections
0
Hubs
–
Fastest
–
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.
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
ORL → MDW
84%
Generally reliable. Most flights run on time.
Arriving
84%
Return
MDW → ORL
75%
Generally reliable. Most flights run on time.
Departing
75%
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 Orlando

Nearby airports with service to Chicago Midway International Airport.
Metric ORL→MDW MCO→MDW LAL→MDW
Distance from ORL – 8 mi 57 mi
Nonstop airlines – 6 1
Weekly flights – 63 –
Flight time 2h 38m 2h 40m 2h 9m
Orlando (MCO) to Chicago flights · Lakeland (LAL) to Chicago flights · Tampa (TPA) to Chicago flights
Airports within 200 miles of ORL 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 Orlando.
ORL: EDT · MDW: CDT

When it's 6:00 PM in Orlando, it's 5:00 PM in Chicago.
Distance & Flight Time
983 mi / 1,582 km
Nonstop flight time is approximately 2h 38m gate to gate.
Facts

ORL–MDW Quick Facts

Key statistics for the Orlando to Chicago route.
Route details
Distance983 mi / 1,582 km
Flight time2h 38m
Time difference-1 hour
Airlines (nonstop)1
1-stop connectionsAvailable
Origin: ORL
Full nameOrlando Executive Airport
IATA / ICAOORL / KORL
TimezoneAmerica/New_York
Elevation113 ft / 34 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 ORL to MDW flights.
Nonstop flights from Orlando Executive Airport to Chicago Midway International Airport take about 2h 38m gate to gate. The route covers 983 miles.
1 airline operated the nonstop from ORL to MDW: Nationwide Airlines. The last scheduled nonstop was in June 2026. There's no nonstop right now, so today you'd fly it with one stop. See the connection options above, ranked by layover.
Not right now. The last scheduled nonstop was in June 2026. You can still fly it with one stop, and the connecting options above are sorted by layover. Nonstop, the hop took about 2h 38m.
Yes, 1-stop connections are available, ranked by layover time.
Chicago is 1 hour behind Orlando.
Yes, return flights from MDW to ORL are available. Use the direction toggle at the top to view the return schedule.
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 ORL to MDW

Orlando Executive Airport (ORL) and Chicago Midway International Airport (MDW) had nonstop service from Nationwide Airlines, last on the schedule in June 2026. The nonstop is dormant right now, so the way to fly it today is one connection, and the options above are sorted by layover.

ORL to MDW Flight Duration and Schedule

Nonstop flight time from ORL to MDW is about 2 hours 38 minutes gate to gate. The route covers a distance of 983 miles (1,582 km).

Connecting Options and Alternatives

1-stop connecting options are also available. Nearby alternative airports include Orlando (MCO), Lakeland (LAL) and Tampa (TPA).