Flights from Chicago to Hilton Head (MDW → HHH)

MDW
Chicago
Chicago Midway International, USA
HHH
Hilton Head
Hilton Head, USA
Loading map...
No direct flights found. Here are the 7 fastest 1-stop options.
viaCharlotte(CLT)
MDW→CLT+1h 30mCLT→HHH
3h
viaAtlanta(ATL)
MDW→ATL+1h 30mATL→HHH
3h 4m
viaWashington(DCA)
MDW→DCA+1h 30mDCA→HHH
3h 35m
viaPhiladelphia(PHL)
MDW→PHL+1h 30mPHL→HHH
3h 55m
viaNew York(EWR)
MDW→EWR+1h 30mEWR→HHH
4h 8m
viaNew York(LGA)
MDW→LGA+1h 30mLGA→HHH
4h 12m
viaBoston(BOS)
MDW→BOS+1h 30mBOS→HHH
4h 47m
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 Hilton Head? Currently, there are no direct flights from MDW to HHH. 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 → Hilton Head.

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

Try a nearby airport to Chicago

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

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

Or try a nearby airport to Hilton Head

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

MDW → SAV 49 km from HHH Chicago → Savannah USA · 39 destinations MDW → CHS 96 km from HHH Chicago → Charleston USA · 55 destinations MDW → AGS 175 km from HHH Chicago → Augusta USA · 7 destinations MDW → CAE 195 km from HHH Chicago → Columbia USA · 13 destinations MDW → JAX 214 km from HHH Chicago → Jacksonville USA · 50 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 Hilton Head (HHH)

Atlanta (ATL) Boston (BOS) Charlotte (CLT) Chicago (ORD) New York (EWR) New York (LGA) Philadelphia (PHL) Washington (DCA) All 8 destinations →