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

ISM Airport Page →
998 mi airlines 1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 41 1-stop flights Verified 4d 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
Orlando to Chicago
Connecting service available through multiple hubs.
1 Flights/wk 998 mi 2h 40m nonstop -1h behind 41 1-stop hubs

While no nonstop service exists between ISM and MDW, connecting options are available through 41 hubs.

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

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for ISM to MDW.
1-STOP
One-Stop Connections
41
Hubs
~3h
Fastest
~10h
Longest
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
66
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 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 0 5 1
Weekly flights 1 54 –
Flight time 2h 40m 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 40m.
Facts

ISM–MDW Quick Facts

Key statistics for the Orlando to Chicago route.
Route details
Distance998 mi / 1,606 km
Flight time2h 40m
Time difference-1 hour
Airlines (nonstop)0
Weekly flights1 out
1-stop connections41 hubs
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 approximately 2h 40m. The route covers 998 miles.
There are approximately 1 nonstop flights per week from ISM to MDW.
Yes, 1-stop connections are available through BHM, STL, BNA, HHH, SDF, VRB, CHS, CMH, MCO, SRQ, IAD, RDU, PBI, ATL, RSW, DCA, ORD, BUF, BWI, MKE, FLL, OPF, TEB, SYR, MIA, ALB, NAS, HOU, OMA, MSP, DAL, PVD, SAT, GCM, AUS, OKC, SLC, PSP, VNY, LAX and SJC. These options provide additional schedule flexibility.
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 ranges from 2 hours 40 minutes. The route covers a distance of 998 miles (1,606 km).

Connecting Options and Alternatives

41 one-stop connections are available, with the fastest taking approximately 3 hours via BHM. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Orlando (MCO), Lakeland (LAL) and Tampa (TPA).