Flights from Winnipeg to Chicago (YWG → MDW)

YWG
Winnipeg
Winnipeg International, Canada
MDW
Chicago
Chicago Midway International, USA
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No direct flights found. Here are the 10 fastest 1-stop options.
viaMinneapolis(MSP)
YWG→MSP+1h 30mMSP→MDW
2h 55m
viaDenver(DEN)
YWG→DEN+1h 30mDEN→MDW
4h 41m
viaAtlanta(ATL)
YWG→ATL+1h 30mATL→MDW
5h 5m
viaOrlando(MCO)
YWG→MCO+1h 30mMCO→MDW
6h 36m
viaPhoenix(PHX)
YWG→PHX+1h 30mPHX→MDW
6h 49m
viaLas Vegas(LAS)
YWG→LAS+1h 30mLAS→MDW
6h 51m
viaFort Lauderdale(FLL)
YWG→FLL+1h 30mFLL→MDW
7h 17m
viaCancun(CUN)
YWG→CUN+1h 30mCUN→MDW
8h 9m
viaMontego Bay(MBJ)
YWG→MBJ+1h 30mMBJ→MDW
9h 19m
viaPunta Cana(PUJ)
YWG→PUJ+1h 30mPUJ→MDW
10h 19m
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 Winnipeg to Chicago? Currently, there are no direct flights from YWG 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 Winnipeg → Chicago.

Cheap flights from Winnipeg 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 Winnipeg

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

YRL → MDW 275 km from YWG Red Lake → Chicago Canada · 5 destinations YPM → MDW 312 km from YWG Pikangikum → Chicago Canada · 5 destinations FAR → MDW 333 km from YWG Fargo → Chicago USA · 11 destinations

Or try a nearby airport to Chicago

Flights from Winnipeg (YWG) to other airports within 350 km of Chicago.

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

Other flights from Winnipeg (YWG)

Atlanta (ATL) Calgary (YYC) Cancun (CUN) Chicago (ORD) Churchill (YYQ) Denver (DEN) Edmonton (YEG) Flin Flon (YFO) All 42 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 →