Flights from Madison to Chicago (MSN → MDW)

MSN
Madison
Dane Co Rgnl Truax Fld, USA
MDW
Chicago
Chicago Midway International, USA
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No direct flights found. Here are the 18 fastest 1-stop options.
viaDetroit(DTW)
MSN→DTW+1h 30mDTW→MDW
2h 31m
viaMinneapolis(MSP)
MSN→MSP+1h 30mMSP→MDW
2h 36m
viaCharlotte(CLT)
MSN→CLT+1h 30mCLT→MDW
3h 56m
viaAtlanta(ATL)
MSN→ATL+1h 30mATL→MDW
3h 57m
viaWashington(DCA)
MSN→DCA+1h 30mDCA→MDW
3h 58m
viaRaleigh/Durham(RDU)
MSN→RDU+1h 30mRDU→MDW
4h 8m
viaPhiladelphia(PHL)
MSN→PHL+1h 30mPHL→MDW
4h 13m
viaNew York(EWR)
MSN→EWR+1h 30mEWR→MDW
4h 21m
viaNew York(LGA)
MSN→LGA+1h 30mLGA→MDW
4h 24m
viaDallas(DFW)
MSN→DFW+1h 30mDFW→MDW
4h 34m
viaDenver(DEN)
MSN→DEN+1h 30mDEN→MDW
4h 46m
viaBoston(BOS)
MSN→BOS+1h 30mBOS→MDW
4h 53m
viaOrlando(MCO)
MSN→MCO+1h 30mMCO→MDW
5h 29m
viaTampa(TPA)
MSN→TPA+1h 30mTPA→MDW
5h 30m
viaFort Myers(RSW)
MSN→RSW+1h 30mRSW→MDW
5h 55m
viaMiami(MIA)
MSN→MIA+1h 30mMIA→MDW
6h 12m
viaPhoenix(PHX)
MSN→PHX+1h 30mPHX→MDW
6h 52m
viaLos Angeles(LAX)
MSN→LAX+1h 30mLAX→MDW
8h
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 Madison to Chicago? Currently, there are no direct flights from MSN 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 Madison → Chicago.

Cheap flights from Madison 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 Madison

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

RFD → MDW 106 km from MSN Rockford → Chicago USA · 8 destinations MKE → MDW 119 km from MSN Milwaukee → Chicago USA · 34 destinations ATW → MDW 142 km from MSN Appleton → Chicago USA · 23 destinations ORD → MDW 175 km from MSN Chicago → Chicago USA · 282 destinations GRB → MDW 180 km from MSN Green Bay → Chicago USA · 6 destinations

Or try a nearby airport to Chicago

Flights from Madison (MSN) to other airports within 350 km of Chicago.

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

Other flights from Madison (MSN)

Atlanta (ATL) Boston (BOS) Charlotte (CLT) Chicago (ORD) Dallas (DFW) Denver (DEN) Detroit (DTW) Fort Myers (RSW) All 19 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 →