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

HPN Airport Page →
729 mi airlines 3/wk
On-time Some delays Frequent delays
Flight Schedule 0 flights Verified 23m ago
Nonstop 1-Stop 2-Stop Hide separate tickets Hide overnight
  Flight Airline AC Dep Arr Dur OTP Sched  

No flights match your filters.

No nonstop flights on this route. connecting options below.

✦ 1-STOP
✧ 2-STOP Loading...
White Plains to Chicago
Connecting service available through multiple hubs.
3 Flights/wk 729 mi 1h 48m nonstop -1h behind 64 1-stop hubs

While no nonstop service exists between HPN and MDW, connecting options are available through 64 hubs.

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

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for HPN to MDW.
1-STOP
One-Stop Connections
64
Hubs
~3h
Fastest
~27h
Longest
YYZ ~3h 46m TEB ~3h 47m PIT ~3h 57m CLE ~3h 58m IAD ~3h 59m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
1,128
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
69%
Moderate delays possible. Allow buffer time.
Departing
69%
Arriving
82%
Return
MDW → HPN
72%
Moderate delays possible. Allow buffer time.
Departing
72%
Arriving
65%
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 0 2 8
Weekly flights 3 95 4
Flight time 1h 48m 2h 24m 1h 37m
Departure OTP 69% – –
New York (LGA) to Chicago flights · Teterboro (TEB) to Chicago flights · Newark (EWR) 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 48m to 1h 56m.
Facts

HPN–MDW Quick Facts

Key statistics for the White Plains to Chicago route.
Route details
Distance729 mi / 1,172 km
Flight time1h 48m to 1h 56m
Time difference-1 hour
Airlines (nonstop)0
Weekly flights3 out
1-stop connections64 hubs
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 approximately 1h 48m to 1h 56m. The route covers 729 miles.
There are approximately 3 nonstop flights per week from HPN to MDW.
Yes, 1-stop connections are available through YYZ, TEB, PIT, CLE, IAD, BTV, MKE, ESN, SYR, IND, CMH, BNA, CVG, BUF, PHL, BWI, ALB, BHM, BDL, BED, BOS, ACK, OMA, PIE, NAS, PBI, HOU, FXE, BZN, PLS, DEN, ASE, RDU, AUS, RIL, SLC, PDX, PSP, LAS, VNY, TUS, BUR, SJU, LAX, SJC, SFO, SAV, MIA, CLT, TPA, DCA, DTW, STL, ATL, MCO, MSP, LGA, RSW, ORD, SRQ, CHS, FLL, JAX and MYR. These options provide additional schedule flexibility.
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 EWR. 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) are connected through multiple connecting hub airports.

HPN to MDW Flight Duration and Schedule

Nonstop flight time from HPN to MDW ranges from 1 hours 48 minutes to 1 hours 56 minutes. The route covers a distance of 729 miles (1,172 km).

Connecting Options and Alternatives

64 one-stop connections are available, with the fastest taking approximately 3 hours via YYZ. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include New York (LGA), Teterboro (TEB) and Newark (EWR).