Flights from Chicago to Havana (MDW to HAV)

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viaTampa(TPA)

MDW→TPA+1h 30mTPA→HAV

4h 2m

viaMiami(MIA)

MDW→MIA+1h 30mMIA→HAV

4h 11m

viaCancun(CUN)

MDW→CUN+1h 30mCUN→HAV

4h 49m

viaPunta Cana(PUJ)

MDW→PUJ+1h 30mPUJ→HAV

7h 3m

Frequently asked questions

Are there direct flights from Chicago to Havana? Currently, there are no direct flights from MDW to HAV. 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 → Havana.

Try a nearby airport to Chicago

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

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

Or try a nearby airport to Havana

Flights from Chicago (MDW) to other airports within 350 km of Havana.

MDW → VRA 100 km from HAV Chicago → Varadero Cuba · 8 destinations MDW → EYW 185 km from HAV Chicago → Key West USA · 26 destinations MDW → SNU 259 km from HAV Chicago → Santa Clara Cuba · 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 Havana (HAV)

Balboa (BLB) Bogota (BOG) Buenos Aires (EZE) Cancun (CUN) Caracas (CCS) Cayo Coco (CCC) Georgetown (GEO) Grand Cayman Island (GCM) All 32 destinations →

Flights from Chicago to Havana (MDW → HAV)