Flights from Chicago to Santiago (MDW → STI)

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

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

Try a nearby airport to Chicago

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

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

Or try a nearby airport to Santiago

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

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

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 →