White Plains to Chicago (HPN–MDW) — Airlines, Schedules & Connections

HPN Airport Page →
729 mi airlines charter/private 1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 13 1-stop flights Verified 7m ago
Also flown by charter / private operators: NetJets Aviation, Executive Jet Management.
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
DTW Detroit 3h 50m DLVSWS → AFDLKE Detroit (DTW) to Chicago flights
DCA Washington 4h 34m AAASEJA → WN Washington (DCA) to Chicago flights
ATL Atlanta 5h 2m AMDLKE → AFAMDL Atlanta (ATL) to Chicago flights
CLT Charlotte 5h 32m AAEJAEJM → EJAWN Charlotte (CLT) to Chicago flights
MSP Minneapolis 5h 40m DL → AFDLVS Minneapolis (MSP) to Chicago flights
MCO Orlando 6h 40m ADB6 → WN Orlando (MCO) to Chicago flights
RSW Fort Myers 7h 11m B6 → WN Fort Myers (RSW) to Chicago flights
TPA Tampa 7h 15m B6 → NJEWN Tampa (TPA) to Chicago flights
SAV Savannah 7h 17m MX → WN Savannah (SAV) to Chicago flights
FLL Fort Lauderdale 7h 18m ADB6EJA → WN Fort Lauderdale (FLL) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
White Plains to Chicago
Connecting service available through multiple hubs.
1 Airlines 729 mi 1h 45m nonstop -1h behind

HPN–MDW had nonstop service from Contour Airlines, last on the schedule in September 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 729 miles in 1h 45m.

Also explore Browse available seat maps HPN Routes MDW Routes HPN Live Flights MDW Live Flights HPN Delays MDW Delays
All flights from Chicago (MDW) Chicago to White Plains flights
Carriers on this route

Airline Landscape

Carriers that operated nonstop HPN–MDW service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
LF Contour Airlines 0 – – 84% – –
Alliance coverage
Unaffiliated: LF (0 flights/wk, 0%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.
Connections

Connection Landscape

1-stop and 2-stop options for HPN to MDW.
1-STOP
One-Stop Connections
13
Hubs
~3h
Fastest
~19h
Longest
DTW ~3h 50m DCA ~4h 34m ATL ~5h 2m CLT ~5h 32m MSP ~5h 40m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
811
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
HPN → MDW
84%
Generally reliable. Most flights run on time.
Departing
84%
Arriving
82%
Return
MDW → HPN
66%
Moderate delays possible. Allow buffer time.
Departing
66%
Arriving
51%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. HPN delays → MDW delays →
Alternatives

Other ways to reach Chicago from White Plains

Nearby airports with service to Chicago Midway International Airport.
Metric HPN→MDW LGA→MDW TEB→MDW
Distance from HPN – 22 mi 24 mi
Nonstop airlines – 4 34
Weekly flights – 94 9
Flight time 1h 45m 1h 58m 1h 45m
Departure OTP 84% – –
New York (LGA) to Chicago flights · Teterboro (TEB) to Chicago flights · New York (JFK) to Chicago flights
Airports within 200 miles of HPN 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 White Plains.
HPN: EDT · MDW: CDT

When it's 6:00 PM in White Plains, it's 5:00 PM in Chicago.
Distance & Flight Time
729 mi / 1,172 km
Nonstop flight time is approximately 1h 45m gate to gate.
Facts

HPN–MDW Quick Facts

Key statistics for the White Plains to Chicago route.
Route details
Distance729 mi / 1,172 km
Flight time1h 45m
Time difference-1 hour
Airlines (nonstop)1
1-stop connectionsAvailable
Origin: HPN
Full nameWestchester County Airport
IATA / ICAOHPN / KHPN
TimezoneAmerica/New_York
Passengers/yr2.4M
Elevation439 ft / 134 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 HPN to MDW flights.
Nonstop flights from Westchester County Airport to Chicago Midway International Airport take about 1h 45m gate to gate. The route covers 729 miles.
1 airline operated the nonstop from HPN to MDW: Contour Airlines. The last scheduled nonstop was in September 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 September 2026. You can still fly it with one stop, and the connecting options above are sorted by layover. Nonstop, the hop took about 1h 45m.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Detroit Metropolitan Wayne County, Ronald Reagan Washington National and Hartsfield Jackson Atlanta.
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 White Plains.
Yes, return flights from MDW to HPN are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include LGA, TEB 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 HPN to MDW

Westchester County Airport (HPN) and Chicago Midway International Airport (MDW) had nonstop service from Contour Airlines, last on the schedule in September 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.

HPN to MDW Flight Duration and Schedule

Nonstop flight time from HPN to MDW is about 1 hours 45 minutes gate to gate. The route covers a distance of 729 miles (1,172 km).

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Detroit Metropolitan Wayne County, Ronald Reagan Washington National and Hartsfield Jackson Atlanta. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include New York (LGA), Teterboro (TEB) and New York (JFK).