Flights from Toronto to Chicago (YYZ → MDW)

YYZ
Toronto
Pearson International, Canada
MDW
Chicago
Chicago Midway International, USA
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No direct flights found. Here are the 20 fastest 1-stop options.
viaDetroit(DTW)
YYZ→DTW+1h 30mDTW→MDW
2h 20m
viaCleveland(CLE)
YYZ→CLE+1h 30mCLE→MDW
2h 27m
viaColumbus(CMH)
YYZ→CMH+1h 30mCMH→MDW
2h 37m
viaIndianapolis(IND)
YYZ→IND+1h 30mIND→MDW
2h 38m
viaPittsburgh(PIT)
YYZ→PIT+1h 30mPIT→MDW
2h 40m
viaCincinnati(CVG)
YYZ→CVG+1h 30mCVG→MDW
2h 45m
viaSaint Louis(STL)
YYZ→STL+1h 30mSTL→MDW
3h 13m
viaWashington(DCA)
YYZ→DCA+1h 30mDCA→MDW
3h 19m
viaPhiladelphia(PHL)
YYZ→PHL+1h 30mPHL→MDW
3h 25m
viaMinneapolis(MSP)
YYZ→MSP+1h 30mMSP→MDW
3h 27m
viaNashville(BNA)
YYZ→BNA+1h 30mBNA→MDW
3h 28m
viaNew York(EWR)
YYZ→EWR+1h 30mEWR→MDW
3h 29m
viaNew York(LGA)
YYZ→LGA+1h 30mLGA→MDW
3h 32m
viaCharlotte(CLT)
YYZ→CLT+1h 30mCLT→MDW
3h 43m
viaRaleigh/Durham(RDU)
YYZ→RDU+1h 30mRDU→MDW
3h 43m
viaBoston(BOS)
YYZ→BOS+1h 30mBOS→MDW
3h 57m
viaAtlanta(ATL)
YYZ→ATL+1h 30mATL→MDW
4h 1m
viaCharleston(CHS)
YYZ→CHS+1h 30mCHS→MDW
4h 20m
viaJacksonville(JAX)
YYZ→JAX+1h 30mJAX→MDW
4h 51m
viaNew Orleans(MSY)
YYZ→MSY+1h 30mMSY→MDW
5h 10m
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 Toronto to Chicago? Currently, there are no direct flights from YYZ 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 Toronto → Chicago.

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

Try a nearby airport to Toronto

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

YTZ → MDW 18 km from YYZ Toronto → Chicago Canada · 19 destinations YHM → MDW 62 km from YYZ Hamilton → Chicago Canada · 12 destinations BUF → MDW 109 km from YYZ Buffalo → Chicago USA · 29 destinations YXU → MDW 144 km from YYZ London → Chicago Canada · 6 destinations ROC → MDW 169 km from YYZ Rochester → Chicago USA · 27 destinations

Or try a nearby airport to Chicago

Flights from Toronto (YYZ) to other airports within 350 km of Chicago.

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

Other flights from Toronto (YYZ)

Abu Dhabi (AUH) Accra (ACC) Addis Ababa (ADD) Amsterdam (AMS) Antigua (ANU) Aruba (AUA) Athens (ATH) Atlanta (ATL) All 194 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 →