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

MDW Airport Page →
998 mi airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 3 1-stop flights Verified 2mos 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
MKE Milwaukee ~4h 40m WN → SGX Milwaukee (MKE) to Orlando flights
PHL Philadelphia ~5h 39m EJAWN → SGX Philadelphia (PHL) to Orlando flights
ALB Albany ~5h 48m WN → Albany (ALB) to Orlando flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Chicago to Orlando
Flown by charter / private operators — no scheduled airline service.
998 mi 2h 2m nonstop +1h ahead

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

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

Connection Landscape

1-stop and 2-stop options for MDW to ISM.
1-STOP
One-Stop Connections
3
Hubs
~4h
Fastest
~5h
Longest
MKE ~4h 40m PHL ~5h 39m ALB ~5h 48m
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 → ISM
49%
Frequent delays expected. Consider flexible booking.
Departing
49%
Return
ISM → MDW
78%
Generally reliable. Most flights run on time.
Arriving
78%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays →
Alternatives

Other ways to reach Orlando from Chicago

Nearby airports with service to Kissimmee Gateway Airport.
Metric MDW→ISM ORD→ISM MKE→ISM
Distance from MDW – 15 mi 81 mi
Nonstop airlines – 1 2
Weekly flights – – 1
Flight time 2h 2m 1h 57m 2h 25m
Departure OTP 49% – –
Chicago (ORD) to Orlando flights · Milwaukee (MKE) to Orlando flights · Kalamazoo (AZO) to Orlando flights
Airports within 200 miles of MDW with service to Kissimmee Gateway Airport.
Know before you go

Travel Essentials

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

When it's 6:00 PM in Chicago, it's 7:00 PM in Orlando.
Distance & Flight Time
998 mi / 1,606 km
Nonstop flight time is approximately 2h 2m gate to gate.
Facts

MDW–ISM Quick Facts

Key statistics for the Chicago to Orlando route.
Route details
Distance998 mi / 1,606 km
Flight time2h 2m
Time difference+1 hour
Airlines (nonstop)Charter / private
1-stop connectionsAvailable
Origin: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
Destination: ISM
Full nameKissimmee Gateway Airport
IATA / ICAOISM / KISM
TimezoneAmerica/New_York
Elevation82 ft / 25 m
FAQ

Frequently Asked Questions

Common questions about MDW to ISM flights.
Nonstop flights from Chicago Midway International Airport to Kissimmee Gateway Airport take about 2h 2m gate to gate. The route covers 998 miles.
Yes, 1-stop connections are available, ranked by layover time.
Orlando is 1 hour ahead of Chicago.
Yes, return flights from ISM to MDW are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include ORD, MKE and AZO. 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 MDW to ISM

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

MDW to ISM Flight Duration and Schedule

Nonstop flight time from MDW to ISM is about 2 hours 2 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. Nearby alternative airports include Chicago (ORD), Milwaukee (MKE) and Kalamazoo (AZO).