Flights from Chicago to Grand Cayman Island (MDW → GCM)

MDW
Chicago
Chicago Midway International, USA
GCM
Grand Cayman Island
Grand Cayman, Cayman Islands
Loading map...
No direct flights found. Here are the 18 fastest 1-stop options.
viaAtlanta(ATL)
MDW→ATL+1h 30mATL→GCM
4h 32m
viaTampa(TPA)
MDW→TPA+1h 30mTPA→GCM
4h 32m
viaOrlando(MCO)
MDW→MCO+1h 30mMCO→GCM
4h 35m
viaMiami(MIA)
MDW→MIA+1h 30mMIA→GCM
4h 36m
viaFort Lauderdale(FLL)
MDW→FLL+1h 30mFLL→GCM
4h 37m
viaCharlotte(CLT)
MDW→CLT+1h 30mCLT→GCM
4h 41m
viaDetroit(DTW)
MDW→DTW+1h 30mDTW→GCM
4h 56m
viaMontego Bay(MBJ)
MDW→MBJ+1h 30mMBJ→GCM
5h 10m
viaBaltimore(BWI)
MDW→BWI+1h 30mBWI→GCM
5h 18m
viaHouston(IAH)
MDW→IAH+1h 30mIAH→GCM
5h 24m
viaPhiladelphia(PHL)
MDW→PHL+1h 30mPHL→GCM
5h 33m
viaDallas(DFW)
MDW→DFW+1h 30mDFW→GCM
5h 34m
viaAustin(AUS)
MDW→AUS+1h 30mAUS→GCM
5h 44m
viaNew York(EWR)
MDW→EWR+1h 30mEWR→GCM
5h 45m
viaMinneapolis(MSP)
MDW→MSP+1h 30mMSP→GCM
5h 45m
viaBoston(BOS)
MDW→BOS+1h 30mBOS→GCM
6h 21m
viaDenver(DEN)
MDW→DEN+1h 30mDEN→GCM
6h 57m
viaLos Angeles(LAX)
MDW→LAX+1h 30mLAX→GCM
9h 31m
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 Chicago to Grand Cayman Island? Currently, there are no direct flights from MDW to GCM. 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 → Grand Cayman Island.

Cheap flights from Chicago to Grand Cayman Island Cheapest month to fly to Grand Cayman Island Flights from USA Flights to Cayman Islands Visa-free with USA passport All airports in Cayman Islands

Try a nearby airport to Chicago

Flights to Grand Cayman Island (GCM) from other airports within 350 km of Chicago. Often unlocks cheaper fares or better times.

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

Other flights from Grand Cayman Island (GCM)

Atlanta (ATL) Austin (AUS) Baltimore (BWI) Boston (BOS) Cayman Brac Island (CYB) Charlotte (CLT) Chicago (ORD) Dallas (DFW) All 30 destinations →