Islip to Chicago (ISP–MDW) — Airlines, Schedules & Connections

ISP Airport Page →
763 mi airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 11 1-stop flights Verified 1mo 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.

Last scheduled nonstop: Aug 2026.

✦ 1-Stop connections via 10 hubs
BWI Baltimore 4h WN → WN Baltimore (BWI) to Chicago flights
BOS Boston 4h 55m 9K → WN Boston (BOS) to Chicago flights
RDU Raleigh/Durham 6h 8m MX → EJAWN Raleigh/Durham (RDU) to Chicago flights
MCO Orlando 6h 20m B6F9WN → WN Orlando (MCO) to Chicago flights
FLL Fort Lauderdale 7h B6 → WN Fort Lauderdale (FLL) to Chicago flights
RSW Fort Myers 8h 26m MX → WN Fort Myers (RSW) to Chicago flights
TPA Tampa 8h 46m F9KOWWN → WN Tampa (TPA) to Chicago flights
MYR Myrtle Beach 14h 42m MX → WN Myrtle Beach (MYR) to Chicago flights
RIC Richmond 15h 14m MX → WNWUP Richmond (RIC) to Chicago flights
ORF Norfolk ~5h 3m MX → WN Norfolk (ORF) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Islip to Chicago
Connecting service available through multiple hubs.
763 mi 1h 58m nonstop -1h behind

While no nonstop service exists between ISP and MDW, 1-stop connecting options are available.

Also explore Browse available seat maps ISP Routes MDW Routes ISP Live Flights MDW Live Flights ISP Delays MDW Delays
All flights from Chicago (MDW) Chicago to Islip flights
Connections

Connection Landscape

1-stop and 2-stop options for ISP to MDW.
1-STOP
One-Stop Connections
11
Hubs
~4h
Fastest
~15h
Longest
BWI ~4h 0m BOS ~4h 55m ORF ~5h 3m STL ~5h 55m RDU ~6h 8m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
494
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.
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
ISP → MDW
100%
Generally reliable. Most flights run on time.
Departing
100%
Arriving
86%
Return
MDW → ISP
56%
Frequent delays expected. Consider flexible booking.
Departing
56%
Arriving
67%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. ISP delays → MDW delays →
Alternatives

Other ways to reach Chicago from Islip

Nearby airports with service to Chicago Midway International Airport.
Metric ISP→MDW HVN→MDW HPN→MDW
Distance from ISP – 34 mi 37 mi
Nonstop airlines – 2 14
Weekly flights – – 1
Flight time 1h 58m 2h 2m 1h 45m
Departure OTP 100% – –
New Haven (HVN) to Chicago flights · White Plains (HPN) to Chicago flights · New York (JFK) to Chicago flights
Airports within 200 miles of ISP 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 Islip.
ISP: EDT · MDW: CDT

When it's 6:00 PM in Islip, it's 5:00 PM in Chicago.
Distance & Flight Time
763 mi / 1,227 km
Nonstop flight time is approximately 1h 58m gate to gate.
Facts

ISP–MDW Quick Facts

Key statistics for the Islip to Chicago route.
Route details
Distance763 mi / 1,227 km
Flight time1h 58m
Time difference-1 hour
Airlines (nonstop)0
1-stop connectionsAvailable
Origin: ISP
Full nameLong Island MacArthur Airport
IATA / ICAOISP / KISP
TimezoneAmerica/New_York
Passengers/yr1.4M
Elevation99 ft / 30 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 ISP to MDW flights.
Nonstop flights from Long Island MacArthur Airport to Chicago Midway International Airport take about 1h 58m gate to gate. The route covers 763 miles.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Baltimore/Washington International Thurgood Marshall, Boston Logan and Raleigh-Durham.
On a single ticket, yes. Your bags are checked through to MDW and move between planes without you. On two separate tickets you collect your bags at the connecting airport and recheck them, so build in extra layover time.
Chicago is 1 hour behind Islip.
Yes, return flights from MDW to ISP are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include HVN, HPN and JFK. 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 ISP to MDW

Long Island MacArthur Airport (ISP) and Chicago Midway International Airport (MDW) are connected through multiple connecting hub airports.

ISP to MDW Flight Duration and Schedule

Nonstop flight time from ISP to MDW is about 1 hours 58 minutes gate to gate. The route covers a distance of 763 miles (1,227 km).

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Baltimore/Washington International Thurgood Marshall, Boston Logan and Raleigh-Durham. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include New Haven (HVN), White Plains (HPN) and New York (JFK).