Flights from Westchester County to Chicago (HPN → MDW)

HPN
Westchester County
Westchester Co, USA
MDW
Chicago
Chicago Midway International, USA
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No direct flights found. Here are the 17 fastest 1-stop options.
viaDetroit(DTW)
HPN→DTW+1h 30mDTW→MDW
2h 53m
viaWashington(DCA)
HPN→DCA+1h 30mDCA→MDW
3h 5m
viaRaleigh/Durham(RDU)
HPN→RDU+1h 30mRDU→MDW
3h 33m
viaCharlotte(CLT)
HPN→CLT+1h 30mCLT→MDW
3h 40m
viaMyrtle Beach(MYR)
HPN→MYR+1h 30mMYR→MDW
4h
viaAtlanta(ATL)
HPN→ATL+1h 30mATL→MDW
4h 6m
viaMinneapolis(MSP)
HPN→MSP+1h 30mMSP→MDW
4h 6m
viaCharleston(CHS)
HPN→CHS+1h 30mCHS→MDW
4h 10m
viaSavannah(SAV)
HPN→SAV+1h 30mSAV→MDW
4h 21m
viaJacksonville(JAX)
HPN→JAX+1h 30mJAX→MDW
4h 44m
viaOrlando(MCO)
HPN→MCO+1h 30mMCO→MDW
5h 14m
viaTampa(TPA)
HPN→TPA+1h 30mTPA→MDW
5h 20m
viaSarasota(SRQ)
HPN→SRQ+1h 30mSRQ→MDW
5h 30m
viaFort Myers(RSW)
HPN→RSW+1h 30mRSW→MDW
5h 41m
viaFort Lauderdale(FLL)
HPN→FLL+1h 30mFLL→MDW
5h 48m
viaMiami(MIA)
HPN→MIA+1h 30mMIA→MDW
5h 51m
viaSan Juan(SJU)
HPN→SJU+1h 30mSJU→MDW
8h 29m
Search all options on Kiwi.com → Total times include an estimated 90-minute layover. Actual times vary by airline and connection.

Frequently asked questions

Are there direct flights from Westchester County to Chicago? Currently, there are no direct flights from HPN to MDW. You may need to connect through another airport.

Related guides for this route

Sibling pages from across Flightmaps — fares, visa rules, country aggregations, and per-airline routes for Westchester County → Chicago.

Cheap flights from Westchester County to Chicago Cheapest month to fly to Chicago Flights from USA Flights to USA Visa-free with USA passport All airports in USA

Try a nearby airport to Westchester County

Flights to Chicago (MDW) from other airports within 350 km of Westchester County. Often unlocks cheaper fares or better times.

LGA → MDW 36 km from HPN New York → Chicago USA · 92 destinations JFK → MDW 48 km from HPN New York → Chicago USA · 201 destinations EWR → MDW 58 km from HPN New York → Chicago USA · 189 destinations SWF → MDW 58 km from HPN Newburgh → Chicago USA · 8 destinations ISP → MDW 60 km from HPN Islip → Chicago USA · 16 destinations

Or try a nearby airport to Chicago

Flights from Westchester County (HPN) to other airports within 350 km of Chicago.

HPN → ORD 25 km from MDW Westchester County → Chicago USA · 282 destinations HPN → SBN 119 km from MDW Westchester County → South Bend USA · 22 destinations HPN → RFD 121 km from MDW Westchester County → Rockford USA · 8 destinations HPN → MKE 130 km from MDW Westchester County → Milwaukee USA · 34 destinations HPN → BMI 175 km from MDW Westchester County → Bloomington USA · 6 destinations

Other flights from Westchester County (HPN)

Atlanta (ATL) Bermuda (BDA) Charleston (CHS) Charlotte (CLT) Chicago (ORD) Daytona Beach (DAB) Detroit (DTW) Fort Lauderdale (FLL) All 26 destinations →

Other flights from Chicago (MDW)

Aguascalientes (AGU) Albany (ALB) Albuquerque (ABQ) Asheville (AVL) Atlanta (ATL) Austin (AUS) Baltimore (BWI) Birmingham (BHM) All 97 destinations →