Flights from Chicago to Winnipeg (MDW → YWG)

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

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

Try a nearby airport to Chicago

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

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

Or try a nearby airport to Winnipeg

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

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

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