Flights from Chicago to Toronto (MDW → YYZ)

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

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

Try a nearby airport to Chicago

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

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

Or try a nearby airport to Toronto

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

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

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