Flights from Chicago to Key West (MDW → EYW)
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viaTampa(TPA)
MDW→TPA+1h 30mTPA→EYW
3h 50m
viaAtlanta(ATL)
MDW→ATL+1h 30mATL→EYW
3h 51m
viaIndianapolis(IND)
MDW→IND+1h 30mIND→EYW
3h 51m
viaNashville(BNA)
MDW→BNA+1h 30mBNA→EYW
3h 52m
viaKnoxville(TYS)
MDW→TYS+1h 30mTYS→EYW
3h 52m
viaCincinnati(CVG)
MDW→CVG+1h 30mCVG→EYW
3h 53m
viaOrlando(MCO)
MDW→MCO+1h 30mMCO→EYW
3h 54m
viaAsheville(AVL)
MDW→AVL+1h 30mAVL→EYW
3h 55m
viaMiami(MIA)
MDW→MIA+1h 30mMIA→EYW
3h 58m
viaCharlotte(CLT)
MDW→CLT+1h 30mCLT→EYW
4h
viaFort Lauderdale(FLL)
MDW→FLL+1h 30mFLL→EYW
4h
viaRaleigh/Durham(RDU)
MDW→RDU+1h 30mRDU→EYW
4h 13m
viaPittsburgh(PIT)
MDW→PIT+1h 30mPIT→EYW
4h 21m
viaWashington(DCA)
MDW→DCA+1h 30mDCA→EYW
4h 35m
viaPhiladelphia(PHL)
MDW→PHL+1h 30mPHL→EYW
4h 54m
viaHouston(IAH)
MDW→IAH+1h 30mIAH→EYW
4h 58m
viaDallas(DFW)
MDW→DFW+1h 30mDFW→EYW
5h 5m
viaNew York(EWR)
MDW→EWR+1h 30mEWR→EYW
5h 6m
viaNew York(LGA)
MDW→LGA+1h 30mLGA→EYW
5h 9m
viaBoston(BOS)
MDW→BOS+1h 30mBOS→EYW
5h 43m
Frequently asked questions
Are there direct flights from Chicago to Key West? Currently, there are no direct flights from MDW to EYW. 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 Chicago → Key West.
Try a nearby airport to Chicago
Flights to Key West (EYW) from other airports within 350 km of Chicago. Often unlocks cheaper fares or better times.
Or try a nearby airport to Key West
Flights from Chicago (MDW) to other airports within 350 km of Key West.