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

ISM Airport Page →
998 mi airlines charter/private ~1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 3 1-stop flights Verified 3w 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 connections via 3 hubs
BWI Baltimore 6h 37m JD → WN Baltimore (BWI) to Chicago flights
RSW Fort Myers ~5h → WN Fort Myers (RSW) to Chicago flights
MKE Milwaukee ~5h 31m → WN Milwaukee (MKE) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Orlando to Chicago
Flown by charter / private operators — no scheduled airline service.
998 mi 2h 22m nonstop -1h behind

ISM–MDW has no scheduled airline service; it is flown by charter / private operators. 1-stop connecting options are also available.

Also explore ISM Routes MDW Routes ISM Live Flights MDW Live Flights MDW Delays
All flights from Chicago (MDW) Chicago to Orlando flights
Connections

Connection Landscape

1-stop and 2-stop options for ISM to MDW.
1-STOP
One-Stop Connections
3
Hubs
~5h
Fastest
~6h
Longest
RSW ~5h 0m MKE ~5h 31m BWI ~6h 37m
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
ISM → MDW
76%
Generally reliable. Most flights run on time.
Arriving
76%
Return
MDW → ISM
51%
Frequent delays expected. Consider flexible booking.
Departing
51%
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 ISM→MDW MCO→MDW LAL→MDW
Distance from ISM – 12 mi 41 mi
Nonstop airlines – 6 1
Weekly flights ~1 63 –
Flight time 2h 22m 2h 40m 2h 9m
Orlando (MCO) to Chicago flights · Lakeland (LAL) to Chicago flights · Tampa (TPA) to Chicago flights
Airports within 200 miles of ISM 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.
ISM: EDT · MDW: CDT

When it's 6:00 PM in Orlando, it's 5:00 PM in Chicago.
Distance & Flight Time
998 mi / 1,606 km
Nonstop flight time is approximately 2h 22m gate to gate.
Facts

ISM–MDW Quick Facts

Key statistics for the Orlando to Chicago route.
Route details
Distance998 mi / 1,606 km
Flight time2h 22m
Time difference-1 hour
Airlines (nonstop)Charter / private
Weekly flights~1 out
1-stop connectionsAvailable
Origin: ISM
Full nameKissimmee Gateway Airport
IATA / ICAOISM / KISM
TimezoneAmerica/New_York
Elevation82 ft / 25 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 ISM to MDW flights.
Nonstop flights from Kissimmee Gateway Airport to Chicago Midway International Airport take about 2h 22m gate to gate. The route covers 998 miles.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Baltimore/Washington International Thurgood Marshall.
Chicago is 1 hour behind Orlando.
Yes, return flights from MDW to ISM 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 ISM to MDW

Kissimmee Gateway Airport (ISM) and Chicago Midway International Airport (MDW) are connected through multiple connecting hub airports.

ISM to MDW Flight Duration and Schedule

Nonstop flight time from ISM to MDW is about 2 hours 22 minutes gate to gate. The route covers a distance of 998 miles (1,606 km).

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Baltimore/Washington International Thurgood Marshall. Nearby alternative airports include Orlando (MCO), Lakeland (LAL) and Tampa (TPA).