Flights from Gulf Shores to Chicago (GUF → MDW)
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viaNashville(BNA)
GUF→BNA+1h 30mBNA→MDW
3h 1m
viaLouisville(SDF)
GUF→SDF+1h 30mSDF→MDW
3h 4m
viaCincinnati(CVG)
GUF→CVG+1h 30mCVG→MDW
3h 9m
viaKnoxville(TYS)
GUF→TYS+1h 30mTYS→MDW
3h 12m
viaKansas City(MCI)
GUF→MCI+1h 30mMCI→MDW
3h 40m
viaDes Moines(DSM)
GUF→DSM+1h 30mDSM→MDW
3h 41m
viaOmaha(OMA)
GUF→OMA+1h 30mOMA→MDW
3h 59m
viaOklahoma City(OKC)
GUF→OKC+1h 30mOKC→MDW
4h 5m
Frequently asked questions
Are there direct flights from Gulf Shores to Chicago? Currently, there are no direct flights from GUF 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 Gulf Shores → Chicago.
Try a nearby airport to Gulf Shores
Flights to Chicago (MDW) from other airports within 350 km of Gulf Shores. Often unlocks cheaper fares or better times.
Or try a nearby airport to Chicago
Flights from Gulf Shores (GUF) to other airports within 350 km of Chicago.