Flights from Chicago to Calgary (MDW → YYC)

MDW
Chicago
Chicago Midway International, USA
YYC
Calgary
Calgary International, Canada
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No direct flights found. Here are the 20 fastest 1-stop options.
viaMinneapolis(MSP)
MDW→MSP+1h 30mMSP→YYC
4h 9m
viaDenver(DEN)
MDW→DEN+1h 30mDEN→YYC
4h 54m
viaDetroit(DTW)
MDW→DTW+1h 30mDTW→YYC
4h 54m
viaSalt Lake City(SLC)
MDW→SLC+1h 30mSLC→YYC
5h 15m
viaNashville(BNA)
MDW→BNA+1h 30mBNA→YYC
5h 28m
viaSeattle(SEA)
MDW→SEA+1h 30mSEA→YYC
5h 37m
viaPortland(PDX)
MDW→PDX+1h 30mPDX→YYC
5h 50m
viaDallas(DFW)
MDW→DFW+1h 30mDFW→YYC
5h 54m
viaAtlanta(ATL)
MDW→ATL+1h 30mATL→YYC
6h 14m
viaCharlotte(CLT)
MDW→CLT+1h 30mCLT→YYC
6h 20m
viaLas Vegas(LAS)
MDW→LAS+1h 30mLAS→YYC
6h 20m
viaAustin(AUS)
MDW→AUS+1h 30mAUS→YYC
6h 30m
viaHouston(IAH)
MDW→IAH+1h 30mIAH→YYC
6h 33m
viaPhoenix(PHX)
MDW→PHX+1h 30mPHX→YYC
6h 33m
viaNew York(EWR)
MDW→EWR+1h 30mEWR→YYC
6h 39m
viaNew York(LGA)
MDW→LGA+1h 30mLGA→YYC
6h 42m
viaSan Francisco(SFO)
MDW→SFO+1h 30mSFO→YYC
6h 56m
viaBoston(BOS)
MDW→BOS+1h 30mBOS→YYC
7h 4m
viaLos Angeles(LAX)
MDW→LAX+1h 30mLAX→YYC
7h 6m
viaSan Diego(SAN)
MDW→SAN+1h 30mSAN→YYC
7h 12m
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 Calgary? Currently, there are no direct flights from MDW to YYC. 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 → Calgary.

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

Try a nearby airport to Chicago

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

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

Or try a nearby airport to Calgary

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

MDW → YEG 244 km from YYC Chicago → Edmonton Canada · 54 destinations MDW → FCA 315 km from YYC Chicago → Kalispell USA · 17 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 Calgary (YYC)

Abu Dhabi (AUH) Amsterdam (AMS) Anchorage (ANC) Atlanta (ATL) Austin (AUS) Barcelona (BCN) Belize City (BZE) Boston (BOS) All 113 destinations →