Flights from Calgary to Chicago (YYC → MDW)

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

Cheap flights from Calgary 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 Calgary

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

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

Or try a nearby airport to Chicago

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

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

Other flights from Chicago (MDW)

Aguascalientes (AGU) Albany (ALB) Albuquerque (ABQ) Asheville (AVL) Atlanta (ATL) Austin (AUS) Baltimore (BWI) Birmingham (BHM) All 97 destinations →