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

MDW Airport Page →
998 mi airlines 0/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 39 1-stop flights Verified 3w 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
Chicago to Orlando
Connecting service available through multiple hubs.
998 mi 2h 2m nonstop +1h ahead 39 1-stop hubs

While no nonstop service exists between MDW and ISM, connecting options are available through 39 hubs.

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

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for MDW to ISM.
1-STOP
One-Stop Connections
39
Hubs
~4h
Fastest
~33h
Longest
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
42
Candidates
Two-stop connections loaded in the connections tab above.
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 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 0 1 1
Weekly flights 0 – –
Flight time 2h 2m 1h 57m 2h 27m
Departure OTP 100% – –
Chicago (ORD) to Orlando flights · Milwaukee (MKE) 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.
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)0
1-stop connections39 hubs
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 approximately 2h 2m. The route covers 998 miles.
Yes, 1-stop connections are available through PIE, SSI, GSO, SUS, BNA, SRQ, SAV, PBI, CLT, IAD, RDU, CMH, ORD, MKE, OKC, PIT, FLL, ORF, FRG, DCA, EWR, STL, MIA, PHL, ALB, MSP, DAL, LGA, AUS, SAT, BOS, IAH, COS, TUS, LAS, VNY, SJC, OAK and HND. These options provide additional schedule flexibility.
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 and MKE. 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 ranges from 2 hours 2 minutes. The route covers a distance of 998 miles (1,606 km).

Connecting Options and Alternatives

39 one-stop connections are available, with the fastest taking approximately 4 hours via PIE. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD) and Milwaukee (MKE).