Flights from Chicago to Madison (MDW → MSN)

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

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

Try a nearby airport to Chicago

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

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

Or try a nearby airport to Madison

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

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

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