Flights from Gulf Shores to Chicago (GUF → MDW)

GUF
Gulf Shores
Jack Edwards Airport, USA
MDW
Chicago
Chicago Midway International, USA
Loading map...
No direct flights found. Here are the 8 fastest 1-stop options.
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
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 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.

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

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.

PNS → MDW 50 km from GUF Pensacola → Chicago USA · 29 destinations MOB → MDW 70 km from GUF Mobile → Chicago USA · 5 destinations VPS → MDW 110 km from GUF Fort Walton Beach → Chicago USA · 50 destinations GPT → MDW 135 km from GUF Gulfport → Chicago USA · 8 destinations ECP → MDW 180 km from GUF Panama City → Chicago USA · 21 destinations

Or try a nearby airport to Chicago

Flights from Gulf Shores (GUF) to other airports within 350 km of Chicago.

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

Other flights from Gulf Shores (GUF)

Appleton (ATW) Belleville (BLV) Bentonville (XNA) Cincinnati (CVG) Des Moines (DSM) Huntsville (HSV) Kansas City (MCI) Knoxville (TYS) All 13 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 →