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

MDW Airport Page →
763 mi airlines charter/private 2/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 14 1-stop flights Verified 2w 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.

✦ 1-Stop connections via 10 hubs
BWI Baltimore 3h 50m UAWN → WN Baltimore (BWI) to Islip flights
RIC Richmond 4h 31m WN → MX Richmond (RIC) to Islip flights
BOS Boston 4h 41m WN → 9K Boston (BOS) to Islip flights
RDU Raleigh/Durham 4h 48m WN → MX Raleigh/Durham (RDU) to Islip flights
CHS Charleston 5h 50m WN → MX Charleston (CHS) to Islip flights
MCO Orlando 6h 8m WN → B6F9WN Orlando (MCO) to Islip flights
MYR Myrtle Beach 7h 23m WN → F9MX Myrtle Beach (MYR) to Islip flights
TPA Tampa 8h 5m WN → F9WN Tampa (TPA) to Islip flights
RSW Fort Myers 8h 46m WN → MX Fort Myers (RSW) to Islip flights
FLL Fort Lauderdale 13h 58m WN → B6 Fort Lauderdale (FLL) to Islip flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Chicago to Islip
Connecting service available through multiple hubs.
1 Airlines 763 mi 2h 3m nonstop +1h ahead

MDW–ISP had nonstop service from Southwest Airlines, last on the schedule in May 2026. There's no nonstop on it right now, so today you'd fly it with one stop. The connecting options below are sorted by layover. Nonstop, it's about 763 miles in 2h 3m.

Also explore MDW Routes ISP Routes MDW Live Flights ISP Live Flights MDW Delays ISP Delays
All flights from Islip (ISP) Islip to Chicago flights
Carriers on this route

Airline Landscape

Carriers that operated nonstop MDW–ISP service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
WN Southwest Airlines 1 – – 58% – –
Alliance coverage
Unaffiliated: WN (1 flights/wk, 100%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.
Connections

Connection Landscape

1-stop and 2-stop options for MDW to ISP.
1-STOP
One-Stop Connections
14
Hubs
~3h
Fastest
~15h
Longest
BWI ~3h 50m ALB ~3h 54m PHL ~4h 2m RIC ~4h 31m BOS ~4h 41m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
565
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
MDW → ISP
58%
Frequent delays expected. Consider flexible booking.
Departing
58%
Arriving
100%
Return
ISP → MDW
100%
Generally reliable. Most flights run on time.
Departing
100%
Arriving
44%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays → ISP delays →
Alternatives

Other ways to reach Islip from Chicago

Nearby airports with service to Long Island MacArthur Airport.
Metric MDW→ISP MKE→ISP
Distance from MDW – 81 mi
Nonstop airlines – 1
Weekly flights – –
Flight time 2h 3m 1h 36m
Departure OTP 58% –
Milwaukee (MKE) to Islip flights
Airports within 200 miles of MDW with service to Long Island MacArthur Airport.
Know before you go

Travel Essentials

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

When it's 6:00 PM in Chicago, it's 7:00 PM in Islip.
Distance & Flight Time
763 mi / 1,227 km
Nonstop flight time is approximately 2h 3m gate to gate.
Facts

MDW–ISP Quick Facts

Key statistics for the Chicago to Islip route.
Route details
Distance763 mi / 1,227 km
Flight time2h 3m
Time difference+1 hour
Airlines (nonstop)1
1-stop connectionsAvailable
Origin: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
Destination: ISP
Full nameLong Island MacArthur Airport
IATA / ICAOISP / KISP
TimezoneAmerica/New_York
Passengers/yr1.4M
Elevation99 ft / 30 m
FAQ

Frequently Asked Questions

Common questions about MDW to ISP flights.
Nonstop flights from Chicago Midway International Airport to Long Island MacArthur Airport take about 2h 3m gate to gate. The route covers 763 miles.
1 airline operated the nonstop from MDW to ISP: Southwest Airlines. The last scheduled nonstop was in May 2026. There's no nonstop right now, so today you'd fly it with one stop. See the connection options above, ranked by layover.
Not right now. The last scheduled nonstop was in May 2026. You can still fly it with one stop, and the connecting options above are sorted by layover. Nonstop, the hop took about 2h 3m.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Baltimore/Washington International Thurgood Marshall, Richmond and Boston Logan.
Islip is 1 hour ahead of Chicago.
Yes, return flights from ISP to MDW are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include 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 ISP

Chicago Midway International Airport (MDW) and Long Island MacArthur Airport (ISP) had nonstop service from Southwest Airlines, last on the schedule in May 2026. The nonstop is dormant right now, so the way to fly it today is one connection, and the options above are sorted by layover.

MDW to ISP Flight Duration and Schedule

Nonstop flight time from MDW to ISP is about 2 hours 3 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, Richmond and Boston Logan. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Milwaukee (MKE).