Flights from Key West to Chicago (EYW → MDW)

EYW
Key West
Key West International, USA
MDW
Chicago
Chicago Midway International, USA
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No direct flights found. Here are the 20 fastest 1-stop options.
viaTampa(TPA)
EYW→TPA+1h 30mTPA→MDW
3h 50m
viaAtlanta(ATL)
EYW→ATL+1h 30mATL→MDW
3h 51m
viaIndianapolis(IND)
EYW→IND+1h 30mIND→MDW
3h 51m
viaNashville(BNA)
EYW→BNA+1h 30mBNA→MDW
3h 52m
viaKnoxville(TYS)
EYW→TYS+1h 30mTYS→MDW
3h 52m
viaCincinnati(CVG)
EYW→CVG+1h 30mCVG→MDW
3h 53m
viaOrlando(MCO)
EYW→MCO+1h 30mMCO→MDW
3h 54m
viaAsheville(AVL)
EYW→AVL+1h 30mAVL→MDW
3h 55m
viaMiami(MIA)
EYW→MIA+1h 30mMIA→MDW
3h 58m
viaCharlotte(CLT)
EYW→CLT+1h 30mCLT→MDW
4h
viaFort Lauderdale(FLL)
EYW→FLL+1h 30mFLL→MDW
4h
viaRaleigh/Durham(RDU)
EYW→RDU+1h 30mRDU→MDW
4h 13m
viaPittsburgh(PIT)
EYW→PIT+1h 30mPIT→MDW
4h 21m
viaWashington(DCA)
EYW→DCA+1h 30mDCA→MDW
4h 35m
viaPhiladelphia(PHL)
EYW→PHL+1h 30mPHL→MDW
4h 54m
viaHouston(IAH)
EYW→IAH+1h 30mIAH→MDW
4h 58m
viaDallas(DFW)
EYW→DFW+1h 30mDFW→MDW
5h 5m
viaNew York(EWR)
EYW→EWR+1h 30mEWR→MDW
5h 6m
viaNew York(LGA)
EYW→LGA+1h 30mLGA→MDW
5h 9m
viaBoston(BOS)
EYW→BOS+1h 30mBOS→MDW
5h 43m
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 Key West to Chicago? Currently, there are no direct flights from EYW 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 Key West → Chicago.

Cheap flights from Key West 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 Key West

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

VRA → MDW 171 km from EYW Varadero → Chicago Cuba · 8 destinations HAV → MDW 185 km from EYW Havana → Chicago Cuba · 32 destinations MIA → MDW 203 km from EYW Miami → Chicago USA · 197 destinations RSW → MDW 220 km from EYW Fort Myers → Chicago USA · 71 destinations FLL → MDW 234 km from EYW Fort Lauderdale → Chicago USA · 148 destinations

Or try a nearby airport to Chicago

Flights from Key West (EYW) to other airports within 350 km of Chicago.

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

Other flights from Key West (EYW)

Asheville (AVL) Atlanta (ATL) Boston (BOS) Charlotte (CLT) Chicago (ORD) Cincinnati (CVG) Columbus (LCK) Dallas (DFW) 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 →