Flights from Chicago to Sint Maarten (MDW → SXM)

MDW
Chicago
Chicago Midway International, USA
SXM
Sint Maarten
Princess Juliana International, Sint Maarten
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No direct flights found. Here are the 11 fastest 1-stop options.
viaCharlotte(CLT)
MDW→CLT+1h 30mCLT→SXM
5h 39m
viaSan Juan(SJU)
MDW→SJU+1h 30mSJU→SXM
5h 46m
viaBaltimore(BWI)
MDW→BWI+1h 30mBWI→SXM
5h 49m
viaAtlanta(ATL)
MDW→ATL+1h 30mATL→SXM
5h 50m
viaPhiladelphia(PHL)
MDW→PHL+1h 30mPHL→SXM
5h 56m
viaOrlando(MCO)
MDW→MCO+1h 30mMCO→SXM
5h 57m
viaFort Lauderdale(FLL)
MDW→FLL+1h 30mFLL→SXM
6h 2m
viaNew York(EWR)
MDW→EWR+1h 30mEWR→SXM
6h 3m
viaMiami(MIA)
MDW→MIA+1h 30mMIA→SXM
6h 3m
viaBoston(BOS)
MDW→BOS+1h 30mBOS→SXM
6h 25m
viaMinneapolis(MSP)
MDW→MSP+1h 30mMSP→SXM
6h 58m
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 Sint Maarten? Currently, there are no direct flights from MDW to SXM. 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 → Sint Maarten.

Cheap flights from Chicago to Sint Maarten Cheapest month to fly to Sint Maarten Flights from USA Flights to Sint Maarten Visa-free with USA passport All airports in Sint Maarten

Try a nearby airport to Chicago

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

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

Or try a nearby airport to Sint Maarten

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

MDW → AXA 19 km from SXM Chicago → Anguilla Anguilla · 10 destinations MDW → SBH 32 km from SXM Chicago → Saint Barthelemy Saint Barthelemy · 7 destinations MDW → SKB 91 km from SXM Chicago → Saint Kitts St. Kitts and Nevis · 16 destinations MDW → EIS 157 km from SXM Chicago → Beef Island British Virgin Islands · 9 destinations MDW → ANU 172 km from SXM Chicago → Antigua Antigua and Barbuda · 27 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 Sint Maarten (SXM)

Amsterdam (AMS) Anguilla (AXA) Antigua (ANU) Aruba (AUA) Atlanta (ATL) Baltimore (BWI) Beef Island (EIS) Bonaire (BON) All 43 destinations →