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

HPN Airport Page →
729 mi airlines charter/private 2/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 15 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 51m DLVSWS → AFDLKE Detroit (DTW) to Chicago flights
DCA Washington 4h 11m AA → WN Washington (DCA) to Chicago flights
ORD Chicago 4h 48m AAAS → UA Chicago (ORD) to Chicago flights
ATL Atlanta 5h 7m AMDLKE → AFAMDL Atlanta (ATL) to Chicago flights
MYR Myrtle Beach 5h 15m MX → WN Myrtle Beach (MYR) to Chicago flights
RDU Raleigh/Durham 5h 35m EJAMX → WNWUP Raleigh/Durham (RDU) to Chicago flights
CLT Charlotte 5h 42m AA → EJAWN Charlotte (CLT) to Chicago flights
MSP Minneapolis 6h DL → AFDLWN Minneapolis (MSP) to Chicago flights
MCO Orlando 6h 23m ADB6 → WN Orlando (MCO) to Chicago flights
SAV Savannah 7h 6m MX → WN Savannah (SAV) 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 56m nonstop -1h behind

HPN–MDW had nonstop service from Contour Airlines, last on the schedule in August 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 56m.

Also explore 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 – – 56% – –
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
15
Hubs
~3h
Fastest
~13h
Longest
DTW ~3h 51m DCA ~4h 11m ORD ~4h 48m ATL ~5h 7m MYR ~5h 15m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
852
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
56%
Frequent delays expected. Consider flexible booking.
Departing
56%
Arriving
61%
Return
MDW → HPN
30%
Frequent delays expected. Consider flexible booking.
Departing
30%
Arriving
82%
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 31
Weekly flights – 87 4
Flight time 1h 56m 2h 15m 1h 37m
Departure OTP 56% – –
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 56m 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 56m
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 56m 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 August 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 August 2026. You can still fly it with one stop, and the connecting options above are sorted by layover. Nonstop, the hop took about 1h 56m.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Detroit Metropolitan Wayne County, Ronald Reagan Washington National and Chicago O'Hare.
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 August 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 56 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 Chicago O'Hare. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include New York (LGA), Teterboro (TEB) and New York (JFK).