Flights from Santiago to Chicago (STI → MDW)

STI
Santiago
Cibao International, Dominican Republic
MDW
Chicago
Chicago Midway International, USA
Loading map...
No direct flights found. Here are the 7 fastest 1-stop options.
viaOrlando(MCO)
STI→MCO+1h 30mMCO→MDW
5h 7m
viaFort Lauderdale(FLL)
STI→FLL+1h 30mFLL→MDW
5h 10m
viaMiami(MIA)
STI→MIA+1h 30mMIA→MDW
5h 10m
viaPhiladelphia(PHL)
STI→PHL+1h 30mPHL→MDW
5h 30m
viaNew York(EWR)
STI→EWR+1h 30mEWR→MDW
5h 39m
viaSan Juan(SJU)
STI→SJU+1h 30mSJU→MDW
5h 59m
viaBoston(BOS)
STI→BOS+1h 30mBOS→MDW
6h 7m
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 Santiago to Chicago? Currently, there are no direct flights from STI 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 Santiago → Chicago.

Cheap flights from Santiago to Chicago Cheapest month to fly to Chicago Flights from Dominican Republic Flights to USA Visa-free with Dominican Republic passport All airports in USA

Try a nearby airport to Santiago

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

POP → MDW 39 km from STI Puerto Plata → Chicago Dominican Republic · 18 destinations AZS → MDW 92 km from STI El Catey/Samana → Chicago Dominican Republic · 5 destinations JBQ → MDW 113 km from STI Santo Domingo → Chicago Dominican Republic · 6 destinations SDQ → MDW 146 km from STI Santo Domingo → Chicago Dominican Republic · 49 destinations CAP → MDW 171 km from STI Cap Haitien → Chicago Haiti · 11 destinations

Or try a nearby airport to Chicago

Flights from Santiago (STI) to other airports within 350 km of Chicago.

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

Other flights from Santiago (STI)

Boston (BOS) Fort Lauderdale (FLL) Madrid (MAD) Miami (MIA) New York (EWR) New York (JFK) Orlando (MCO) Panama City (PTY) All 11 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 →